Supporting Information
|
|
- Rodger Patterson
- 5 years ago
- Views:
Transcription
1 Nnoporous Polymers Inorporting Sterilly Confine N-Heteroyli Crenes For Simultneous CO 2 Cpture n Conversion t Amient Pressure Siulu Niu Tlpneni, Onur Buyukkir, Sng-hyun Je, Smpth Srinivsn, Yongeom Seo, Kyriki Polyhronopoulou # n Ali Coskun, * Grute Shool of Energy, Environment, Wter n Sustinility (EEWS), Kore Avne Institute of Siene n Tehnology (KAIST), Dejeon , Repuli of Kore. Center for Nnomterils n Chemil Retions, Institute for Bsi Siene (IBS), Dejeon, Repuli of Kore. # Deprtment of Mehnil Engineering, Khlif University, Au Dhi, UAE. Deprtment of Chemistry, Kore Avne Institute of Siene n Tehnology (KAIST), Dejeon , Repuli of Kore. Emil: oskun@kist..kr Supporting Informtion * Corresponene Aress Professor Ali Coskun Grute Shool of EEWS n Deprtment of Chemistry Kore Avne Institute of Siene n Tehnology (KAIST) Guseong Dong, Yuseong Gu, Dejeon (Repuli of Kore). Tel: (+82) Fx: (+82) E-Mil: oskun@kist..kr
2 Contents: Setion 1. Mterils n Instrumenttion S3-S4 Setion 2. Experimentl protools for the preprtion of NP-Imine, NP-Imizolium n NP-N- Heteroyli rene (NP-NHC) S4 Setion 3. Synthesis of onventionl sterilly onfine N-heteroyli rene (NHC) S5-S6 Setion 4. Synthesis n routine hrteriztion of tetrphenyl methne inorporting 2,6- iisopropyl niline hyrohlorie (Compoun6. HCl) S6-S14 Setion 5. Synthesis of non-steri porous NHC (PNHC) s ontrol polymer S15-S16 Setion 6. Routine nlysis of nnoporous polymers S17-S28 Setion 7. Ctlyti onversion of CO 2 to yli rontes on NP-NHC orgnotlyst y using epoxies S29 Setion 8. Chrteriztion of yli rontes y 1 H NMR n gs hromtogrphy (GC) S30-S39 Setion 9. Referenes S40 S2
3 Setion 1. Mterils n Instrumenttion All mnipultions involving ir- n/or moisture-sensitive ompouns were rrie out using glove ox or stnr Shlenk line tehniques uner Ar tmosphere. Air-sensitive liquis were trnsferre vi syringe n were injete into the retion flsk through ruer sept. Moisture sensitive solis were trnsferre in ry gloveox uner Ar tmosphere. Anlytil thin-lyer hromtogrphy ws performe using sili gel pre-ote on luminum sheets. Visuliztion of evelope hromtogrms ws performe y exposure to UV or ioine vpor. Flsh olumn hromtogrphy ws rrie out using mesh sili. All hemils n solvents were purhse from Sigm-Alrih n use without further purifition. The 1 H NMR spetr were reore on Bruker DMX 300 MHz n 13 C NMR spetr were otine using Bruker Avne 400 MHz NMR instrument. Chemil shifts in 1 H NMR spetr re reporte in prts per million (ppm) from tetrmethylsilne, with the solvent resonne use s n internl stnr. Dt re presente in the following orer: hemil shift, multipliity (s = singlet, = oulet, t = triplet, q = qurtet, qn = quintet, sx = sextet, h = heptet, o = otet, m = multiplet, n r = ro), oupling onstnt in Hz, n integrtion. Chemil shifts for 13 C NMR spetr re reporte in prts per million (ppm) from tetrmethylsilne, using the entrl pek of the solvent resonne s the internl stnr. Quntittive nlysis ws onute y Shimzu GC-2010 system running with HP-5MS pillry olumn ws use. FT-IR spetr were reore on ATR moe y using Shimzu FTIR Spetrometer y verging 200 sns with resolution of 2 m -1, mesuring in trnsmission moe. 1 H n 13 C spetr were ollete on Bruker Avne 300 MHz NMR n Agilent 400 MHz NMR spetrometers t mient temperture. Soli-stte rosspolriztion mgi ngle spinning (CP/MAS) 13 C NMR spetr of polymers were tken using Bruker Digitl Avne III HD 400 WB (400 MHz) NMR spetrometer t mient temperture with mgi ngle spinning rte of 7.0 khz. The Ar sorption n esorption isotherms were mesure t 87 K on Mirometris 3Flex Surfe Chrteriztion Anlyzer. All smples were outgsse t 100 o C for 16 h prior to the nlysis. The speifi surfe res of smples were lulte using the BET n Lngmuir moel in the pressure rnge where the term V(1-P/P 0 ) ontinuously inreses with P/P 0 in the Rouquerol plot. The pore size istriutions of smples were lulte from rgon isotherms S3
4 oring to Nonlol Density Funtionl Theory (NLDFT) metho using zeolite ylinril pore moel. The morphology of the mterils ws oserve on Hithi S-4800 fiel emission snning eletron mirosope using n elerting voltge of 5.0 kv. Elementl nlysis (C, H, N) ws one on FlshEA 2000 (Series) [C, H, N, S] Elementl Anlyzer. Power X-ry iffrtion (PXRD) ptterns of the smples were quire from 2 to 70 y Rigku D/MAX (18 kw) mirore X-ry iffrtometer. Thermogrvimetri nlysis (TGA) ws performe on NETZSCH-TG 209 F3 instrument uner nitrogen or CO 2 tmospheres (flow rtes: 10 ml min -1 ). Quntittive nlysis ws onute y Shimzu GC-2010 system running with HP-5MS pillry olumn ws use. Setion 2. Experimentl protools for the synthesis of NP-Imine, NP- Imizolium n NP-N-Heteroyli rene (NP-NHC) Synthesis of NP-Imine. A 10-mL pyrex tue ws hrge with the orresponing romti tetrmine tetrhyrohlorie (50 mg, 0.04 mmol), glyoxl of 40 wt% in H 2 O (5.0 mg, ml, mmol), n 2.4 ml mixture of ioxne n 3M eti i (1/0.2 in v/v). The mixture ws ultrsonite for 30 min t 25 C n egsse using three freeze-pump-thw yles. The tue ws then sele n kept in n utolve t 120 C for 3 ys. The preipitte ws filtere off, wshe with ry ioxne (2 x 100 ml), THF (2 x 100 ml) n CH 2 Cl 2 (2 x 100 ml), n ws lyophilize t room temperture for 16 h to yiel NP-Imine s power in 90% yiel. Elementl nlysis (Clulte): C: 86.8%, N: 5.26%, H: 7.05%; Elementl nlysis (Experimentl): C: 82.36%, N: 4.86%, H: 7.64%. Synthesis of NP-Imizolium. To 50.0 mg of the NP-Imine in 2.0 ml of THF, n exess of prformlehye (14.2 mg, 0.47 mmol) ws e t one. Afterwrs, the retion mixture ws hete to 100 C until most of prformlehye ws issolve. It ws then oole to 40 C n 0.14 ml of HCl (0.47 mmol, 4M in ioxne) ws e vi syringe uner Ar tmosphere. The retion mixture ws hete to 80 C n kept t this temperture for 2 ys n then kept t room temperture for 24 h. The light rown preipitte ws ollete y filtrtion n wshe with THF (2 x 100 ml), n ws lyophilize t room temperture for 16 h to yiel NP- Imizolium in power form in 80% yiel. Elementl nlysis (Clulte): C: 81.6%, N: 4.82%, H: 7.46%, Cl: 5.95%; Elementl nlysis (Exp): C: 79.19%, N: 4.57%, H: 7.53%. Synthesis of NP-NHC. To mixture of 55 mg of the NP-Imizolium in 2 ml of ry THF, 57.0 mg of potssium tert-utoxie (0.5 mmol) ws e. The resulting mixture ws stirre for 3 ys t room temperture. The preipitte ws filtere off n wshe with exess THF (3 x 100 ml) n ethnol (2 x 100 ml). The resulting power ws lyophilize t room temperture for 16 h to yiel NP-NHC (45 mg, 93%). Elementl nlysis (Clulte for NP-NHC): C: 87.09%, N: 4.63%, H: 7.77 %; Elementl nlysis (Experimentl): C: 81.19%, N: 4.57%, H: 7.50%. S4
5 Setion 3. Synthesis of onventionl sterilly onfine N-heteroyli rene (NHC) The onventionl IPr NHC ws prepre y following the syntheti proeure reporte y Noln et l. 1 n use s referene to nlyze struturl fetures of NP-NHC. Formi i H O NH 2 N N N N + H O Ethnol / RT / 2 Toluene / 100 o C / 70 o C to RT / 2 H Cl 72% p-formlehye / HCl 42% IPr.HCl N N IPr.NHC KO t Bu THF / RT / 4 h 69% Figure S1. Syntheti sheme for the preprtion of onventionl IPr NHC. 1 Synthesis of is(2,6-iisopropylphenyl)izutiene. A 100 ml roun-ottom flsk ws hrge with 10 g (56.4 mmol) of 2,6-iisopropylniline, 4.1 ml (28.2 mol, 40% in wter) of glyoxl n 50 ml of solute EtOH. A few rops of formi i were e s tlyst. The olor of the retion mixture turne from olorless to yellow immeitely n the formtion of yellow preipitte ws oserve fter few hours. The retion mixture ws stirre for two ys t room temperture. The yellow soli ws ollete y filtrtion n wshe with ol MeOH to ffor the nlytilly pure ompoun. Yiel = 7.5 g (72%). Synthesis of Synthesis of IPr HCl. To solution of is(2,6-iisopropylphenyl)izutiene (6 g, 16 mmol) in toluene (120 ml) ws e 0.48 g (16 mmol) of prformlehye in soli form. The retion mixture ws hete to 100 C until most of prformlehye ws issolve. It ws then oole to 40 C n 4.5 ml of HCl (16 mmol, 4 M in ioxne) ws e vi syringe. The retion mixture ws hete to 70 C for 5 h uring whih the olor of the retion mixture turne rown n the formtion of white preipitte ws oserve. The retion mixture ws then llowe to stir t room temperture for 36 h. The off-white preipitte ws ollete y filtrtion n wshe with THF. Yiel = 2.9 g (42%). Synthesis of Synthesis of IPr NHC. To mixture of IPr.HCl (1.5 g, 3.46 mmol) n KO t Bu (0.43 g, 3.81 mmol) ws e THF (15 ml) t room temperture. The olor of the solution turne to rown olor immeitely n the formtion of white preipitte ws oserve. The S5
6 retion mixture ws stirre for 4 h t room temperture. The solvent ws remove uner vuum n the resiue ws tken up in hot toluene (70 C). The retion mixture ws then filtere through Celite n the evportion of the voltiles ffore rown soli. Yiel = 0.9 g (69%). Setion 4. Synthesis n routine hrteriztion of tetrphenyl methne inorporting 2,6-iisopropyl niline hyrohlorie (ompoun 6.HCl) Br 2 NH 2 Br NH 2 DCM / MeOH / 25 o C / 20 h 92% Benzophenone TEOS / t. H 2 SO 4 Br N 150 o C / % 2 O B O N 3 Bis(Pinolto)ioron / [PCl 2 (ppf)] / KOA DMSO / 80 o C / 2 50% N Br Br 4 Br Br + O B O 3 N [PCl 2 (ppf)] / CsF Dioxne : Wter (1:1) Reflux / 2 30% N N N NH 2 5 H 2 N Figure S2. Synthesis of ompoun 6.HCl. NH 2.4HCl 6 NH 2 4M HCl THF / 80 o C / 16 h 80% S6
7 Synthesis of ompoun 1. 2 To suspension of 2,6-iisopropyl niline (18.8 g, 106 mmol) in 50 ml CH 2 Cl 2 : MeOH (1:1) mixture, Br 2 (17.07 g, 214 mmol) in 50 ml CH 2 Cl 2 : MeOH (1:1) mixture ws e ropwise over 30 min. The mixture ws stirre t 25 C for 20 h, yieling rk olore suspension. After omplete onsumption of the strting mteril, the solvent ws remove uner reue pressure. The otine rue prout ws rerystllize from 1:1 mixture of CH 2 Cl 2 : hexne (50 ml). The preipitte ws filtere n wshe with 20 ml of ol hexne. The resiue ws neutrlize y treting with 150 ml (5 ml g -1 ) of 20 wt% queous NOH solution for 4 h. Upon extrtion with iethyl ether for three times, the orgni extrts were omine, rie over soium sulfte, n filtere. Removl of voltiles uner reue pressure yiels 25.0 g (92%) of the ompoun 1 s yellow oil. 1 H NMR (300 MHz, CDCl 3 ) = δ (r, 2H), 7.37 (s, 2H), (m, 2H), 1.30 (, J = 6.7 Hz, 12H) ppm. X X Figure S3. 1 H NMR (300 MHz, CDCl 3, 298 K) spetrum of ompoun 1. Synthesis of ompoun 2. Compoun 2 ws prepre y following the moifie proeure reporte y Lee et l. 2 To 250 ml flsk ontining ompoun 1 (8.0 g, 33.2 mmol) n enzophenone (8.53 g, 46.8 mmol) were e tetrethylorthosilite (130 ml, mmol) n S7
8 H 2 SO 4 (0.5 ml). The solution ws hete for 2 ys t 150 C uner Ar tmosphere. The retion mixture ws oole to room temperture, ilute with iethyl ether n wshe with 1M queous NOH solution n susequently with rine solution. Orgni lyer ws seprte, rie over N 2 SO 4 n onentrte uner reue pressure. The onentrte solution ws ilute with ethnol n 10 ml of ethnoli 1 M KOH (issolve in EtOH) solution ws e. The resulting mixture ws stirre t room temperture overnight. The suspension ws filtere n remining soli ws wshe with exess of iethyl ether. The omine filtrtes were wshe with H 2 O n rine solution. The orgni lyer ws rie over N 2 SO 4, filtere n evporte. The rue prout ws sujete to sili gel olumn hromtogrphy with hexne s the moile phse. Conentrte olumn frtions were llowe to rystlize in hexne to yiel reish yellow olore ompoun 2 (6.3g, 45%). 1 H NMR (300 MHz, CDCl 3 ) = δ 7.79 (, J = 7.3 Hz, 2H), 7.44 (, J = 6.7 Hz, 3H), (m, 3H), 7.07 (, J = 2.3 Hz, 4H), 2.83 (m, J = 13.6, 6.8 Hz, 2H), 1.12 (, J = 6.4 Hz, 6H), 0.93 (, J = 6.5 Hz, 6H) ppm. Figure S4. 1 H NMR (300 MHz, CDCl 3, 298 K) spetrum of ompoun 2. S8
9 Synthesis of ompoun 3. In flme-rie 250 ml triple nek roun ottom flsk, ompoun 2 (2.0 g, 4.75 mmol) ws isperse in 80 ml of Argon purge ry DMSO. Bis(pinolto)ioron (1.27 g, 4.98 mmol), KOA (1.4 g, mmol) n P(ppf)Cl 2 (0.12 g, 0.14 mmol) were e into the retion mixture while vigorously stirring the solution. The retion mixture ws then hete to 80 C for 2 ys. After ooling own to the room temperture, the retion mixture ws ilute with toluene n wshe with exess mount of H 2 O n rine in orer to remove DMSO. The toluene lyer ws rie over N 2 SO 4, filtere n evporte. The rue prout ws sujete to sili gel olumn hromtogrphy. The unrete strting mteril ws reovere with CHCl 3 : hexne (1:1) eluent n then the prout elute with CHCl 3. The olumn frtions were onentrte to yiel yellow olore ompoun 3 (1.1 g, 50 %). 1 H NMR (300 MHz, CDCl 3 ) = δ 7.78 (s, 2H), 7.43 (m, 4H), 7.26 (s, 6H), 2.86 (m, J = 13.7, 6.9 Hz, 2H), 1.33 (s, 12H), 1.12 (, 6H), (, 6H) ppm. 13 C NMR (100 MHz, CDCl 3 ) = δ 165.7, 145.8, 145.1, 138.9, 135.9, 135.0, 131.2, 129.2, 128.9, 127.9, 127.5, 125.5, 121.2, 63.9, 28.4, 23.8, 21.8 ppm. MALDI-TOF-MS for C 31 H 38 BNO 2 (lulte: ), foun: ([M] + ). Figure S5. 1 H NMR (300 MHz, CDCl 3, 298 K) spetrum of ompoun 3. S9
10 Figure S6. 13 C NMR (100 MHz, CDCl 3, 298 K) spetrum of ompoun 3. Synthesis of ompoun 4. The synthesis of ompoun 4 ws performe using previously reporte literture proeure. 3 A 150 ml roun ottom flsk equippe with mgneti stir r n wter-oole reflux onenser ws hrge with tetrphenylmethne (9 g, 28 mmol). Net Br 2 (10 ml, 196 mmol) ws slowly e n the resulting solution ws stirre for 1 h t room temperture. The rk slurry ws ilute with ethnol (200 ml) n further stirre for 30 min. The preipitte ws then filtere n oile in mixture of EtOH : CHCl 3 (1:1 v/v, 400 ml) for 10 min. The solution ws llowe to ool to room temperture. The preipitte soli ws filtere n rie uner ynmi vuum to ffor ompoun 4 s n off white soli (11.7 g, 66% yiel). 1 H NMR (300 MHz, CDCl 3 ): δ 7.39 (, J = 8.8 Hz, 8H), 7.01 (, J = 8.8 Hz, 8H) ppm. X X Figure S7. 1 H NMR (300 MHz, CDCl 3, 298 K) spetrum of ompoun 4. S10
11 Synthesis of ompoun 5. Compoun 3 (3 g, 6.42 mmol), ompoun 4 (0.7g, 1.07 mmol), CsF (1.95 g, mmol) n P(ppf)Cl 2 (0.175g, 0.21 mmol) were e into Shlenk flsk insie gloveox. Degsse ioxne (14 ml) n egsse H 2 O (7 ml) were e to the flsk whih ws then sele n hete to reflux for 2 ys. After ooling own to the room temperture, the retion mixture ws ilute with EtOA n filtere. The filtrte ws wshe with wter n rine solutions suessively. The EtOA lyer ws rie over N 2 SO 4, filtere n evporte. The otine rue prout ws sujete to sili gel olumn hromtogrphy with EtOA : hexne s n eluent. Column frtions were omine n onentrte to yiel rk yellow olore ompoun 5 (0.5g, 30%). 1 H NMR (300 MHz, CDCl 3 ) = δ 7.81 (, J = 7.0 Hz, 8H), (m, 34H), (m, 22H), (m, 8H), 1.18 (, J = 5.9 Hz, 24H), 0.97 (, J = 6.1 Hz, 24H) ppm. 13 C NMR (100 MHz, CDCl 3 ) = δ 164.9, 149.3, 134.6, 129.3, 129.0, 127.7, 83.1, 28.3, 24.8 ppm. MALDI-TOF-MS for C 125 H 120 N 4 (lulte: ), foun: ([M] + ). S11
12 X X g f e e, f & g & X e f & g & Figure S8. 1 H NMR (300 MHz, CDCl 3, 298 K) spetrum of ompoun 5. Figure S9. 13 C NMR (100 MHz, CDCl 3, 298 K) spetrum of ompoun 5. S12
13 Synthesis of ompoun 6. Compoun 5 (0.5 g, 0.3 mmol) ws issolve in 150 ml of THF n hrge with 20 ml of 4 N queous HCl. The resulting solution ws sujete to heting t 70 C n kept t this temperture for 12 h. The olor of the solution hnge from yellow to olorless uring the ourse of the retion. After ooling own to the room temperture, the retion mixture ws filtere n the preipitte ws stirre in EtOA (to remove the enzophenone imine y prout) for 2 h n gin filtere to yiel white olor ompoun 6 (0.3g, 80%). Compoun 6 ws neutrlize using 1 M queous NOH solution n extrte with EtOA to get the orresponing free mine. 1 H NMR (300 MHz, CDCl 3 ) = δ 7.49 (, J = 8.1 Hz, 8H), 7.37 (, J = 8.2 Hz, 8H), 7.31 (s, 8H), 3.79 (r, 8H), 2.97 (m, J = 13.6, 6.8 Hz, 8H), (, 48H) ppm. 13 C NMR (100 MHz, CDCl 3 ) = δ 144.8, 139.5, 139.3, 132.6, 131.3, 130.8, 125.4, 125.3, 121.5, 63.8, 27.9, 22.4 ppm. MALDI-TOF-MS for C 73 H 88 N 4 (lulte: ), foun: ([M] + ). e X e f e X f Figure S10. 1 H NMR (300 MHz, CDCl 3, 298 K) spetrum of ompoun 6. S13
14 Figure S C NMR (100 MHz, CDCl 3, 298 K) spetrum of ompoun 6. S14
15 Setion 5. Synthesis of non-steri porous NHC (PNHC) s ontrol polymer In orer to emonstrte the importne of steri onfinement in NP-NHC, non-steri porous NHC (PNHC) 4 hs een prepre uner ientil syntheti onitions to tht of NP-NHC strting from tetrkis(4-minophenyl)methne s shown elow. PImin PNHC PImCl Figure S12. Syntheti sheme for the preprtion of non-steri porous imine (PImin), imizolium hlorie (PImCl), N-heteroyli rene (PNHC). The lines t terminl positions imply the extension of perioi strutures. 4 S15
16 Non-steri porous imine (PImin). A 10-mL pyrex tue ws hrge with tetrkis(4- minophenyl)methne (60 mg, 0.15 mmol), glyoxl of 40 wt% in H 2 O (18.3 mg, 0.45 ml, mmol), n 3.0 ml mixture of ioxne n 3M queous eti i solution (1/0.2 in v/v). The mixture ws ultrsonite for 30 min t 25 C n egsse using three freeze-pump-thw yles. The tue ws then sele n kept in n utolve t 140 C for 3 ys. The preipitte ws filtere off, wshe with ioxne (2 x 100 ml), THF (2 x 100 ml) n CH 2 Cl 2 (2 x 100 ml), n ws lyophilize t room temperture for 16 h to yiel PImin in 95% yiel. Non-steri porous imizolium hlorie (PImCl). To 70.0 mg of the PImin in 3.0 ml of THF n exess of prformlehye (15.8 mg, mmol) ws e in soli form. The retion mixture ws hete to 100 C until most of prformlehye ws issolve. It ws then oole to 40 C n 0.15 ml of HCl (0.52 mmol, 4 M in ioxne) ws syringe in. The retion mixture ws hete to 80 C for 2 ys n llowe to stir t room temperture for itionl 24 h. The rown olore preipitte ws ollete y filtrtion n wshe with THF (100 ml), n lyophilize t room temperture for 16 h to yiel PImCl in 85% yiel. Non-steri porous N-heteroyli rene (PNHC). To mixture of 75 mg of the PImCl in 3 ml of ry THF, 70.0 mg of potssium tert-utoxie (0.63 mmol) ws e. The resulting mixture ws stirre for 3 ys n filtere off n the preipitte ws wshe with THF (3 x 100 ml) n EtOH (2 x 100 ml). The resulting power ws lyophilize t room temperture for 16 h to yiel PNHC (yiel: 70 mg, 93%). S16
17 Trnsmission (%) -NH 2 :3400 Amine NP-Imine Wvenumer, m -1 Figure S13. FT-IR spetr of sterilly onfine nnoporous imine (NP-Imine) n the orresponing extene romti tetrmine erivtive. S17
18 NHC-CO 2 :1621 Trnsmission (%) NP-NHC NP-Imizolium C=N:1705 NP-Imine Wvenumer, m -1 Figure S14. Enlrge ( m -1 ) FT-IR spetr of sterilly onfine nnoporous imine (NP-Imine), imizolium (NP-imizolium) n N-heteroyli rene (NP-NHC). Re otte lines inite key FT-IR ns ssoite with the rene n orresponing imizolium roxylte moieties. S18
19 Trnsmission (%) Crene 1700 Ipr-CO 2 :1675 IPr IPr.HCl C=N:1625 Imine Wvenumer, m -1 Figure S15. Enlrge ( m -1 ) FT-IR spetr of onventionl imine, imizolium n N-heteroyli rene (IPr NHC). Re otte line inites omplete ispperne of imine strething ns following yliztion. In ition hrteristi IR signtures of rene is lso highlighte. S19
20 Trnsmission (%) PNHC PImizolium PImine Wvenumer, m -1 Figure S16. Enlrge ( m -1 ) FT-IR spetr of non-steri ontrol polymer, PImine, PImCl n PNHC. Re otte line inites omplete ispperne of imine strething ns following yliztion. In ition hrteristi IR signtures of rene is lso highlighte. S20
21 Intensity (.u.) NP-Imine NP-Imizolium NP-NHC θ (Degree) Figure S17. Power X-ry iffrtion (XRD) ptterns of NP-Imine, NP-Imizolium n NP- NHC. S21
22 NP-Imine NP-Imizolium NP-NHC Figure S18. Fiel emission snning eletron mirosopy (FE-SEM) imges of NP-imine, NPimizolium n NP-NHC. SEM imges show the formtion of irregulr size spheril prtiles. S22
23 NP-Imine NP-Imizolium NP-NHC Mss (%) Temperture ( o C) Figure S19. Thermogrvimetri nlysis (TGA) of NP-Imine, NP-Imizolium n NP-NHC uner ir tmosphere up to 800 C t rte of 10 C min -1. S23
24 150 () V(1-P/P 0 ), m 3 g V(1-P/P 0 ), m 3 g Reltive pressure, P/P () Reltive pressure, P/P /[Q(P 0 /P - 1] BET : 483 ± 5 m²/g R 2 : y = x + 4X Reltive pressure, P/P 0 Figure S20. () Clulte Rouquerol plot for NP-Imine (Inset: enlrge plot) long with the pressure rnges use for the BET surfe re lultions. We hve use the pressure rnge where the term V(1-P/P 0 ) ontinuously inreses with P/P 0 for the surfe re lultions; () BET plot of NP-Imine otine from rgon isotherms t 87 K. The selete points re lote in the pressure rnges of 0.01 to 0.12 oring to the Rouquerol plots. S24
25 150 () V(1-P/P 0 ), m 3 g V(1-P/P 0 ), m 3 g Reltive pressure, P/P () Reltive pressure, P/P 0 1/[Q(P 0 /P - 1] BET : 537 ± 6 m²/g R 2 : y = x + 3X Reltive pressure, P/P 0 Figure S21. () Clulte Rouquerol plot for NP-Imizolium (Inset: enlrge plot) long with the pressure rnges use for the BET surfe re lultions. We hve use the pressure rnge where the term V(1-P/P 0 ) ontinuously inreses with P/P 0 for the surfe re lultions; () BET plot of NP-Imizolium otine from rgon isotherms t 87 K. The selete points re lote in the pressure rnges of 0.01 to 0.12 oring to the Rouquerol plots. S25
26 125 () V(1-P/P 0 ), m 3 g V(1-P/P 0 ), m 3 g Reltive pressure, P/P () Reltive pressure, P/P 0 1/[Q(P 0 /P - 1] BET : ± m²/g R 2 : y = x + 7X Reltive pressure, P/P 0 Figure S22. () Clulte Rouquerol plot for the NP-NHC (Inset: enlrge plot) long with the pressure rnges use for the BET surfe re lultions. We hve use the pressure rnge where the term V(1-P/P 0 ) ontinuously inreses with P/P 0 for the surfe re lultions; () BET plot of NP-NHC otine from rgon isotherms t 87 K. The selete points re lote in the pressure rnges of 0.01 to 0.12 oring to the Rouquerol plots. S26
27 Quntity sore, m 3 g () PImin PImCl PNHC Reltive pressure, P/P 0 Differentil pore volume, m 3 g () PImin PImCl 0.4 PNHC Pore size, nm Smple nme S BET (m 2 g -1 ) Lngmuir (m 2 g -1 ) V miro (m 3 g -1 ) miro (nm) S ext (m 2 g -1 ) S miro (m 2 g -1 ) V totl e (m 3 g -1 ) PImin PImCl PNHC Brunuer Emmett Teller (BET) surfe re lulte over the pressure rnge (P/P 0) Miropore volume lulte using the t-plot metho. Miropore imeter lulte from NLDFT metho. Miropore surfe re lulte from the sorption isotherm using the t-plot metho. e Totl pore volume otine t P/P 0 = Figure S23. ) Argon sorption esorption isotherms (open n lose symols represent esorption n sorption, respetively) n () NLDFT pore-size istriutions ( re squres: PImin, lue tringles: PImin, n green imons: PNHC) long with texturl prmeters of non-steri PImin, PImCl n PNHC mesure t 87 K. S27
28 CO 2 Fixing effiieny (%) 160 o C N o C N 2 25 / 40 / 80 / 120 o C 25 / 40 / 80 / 120 o C CO 2 CO 2 25 o C 40 o C 80 o C 120 o C Time (min) Figure S24. TGA urves for CO 2 pture-relese performne of non-steri PNHC t 25, 40, 80 n 120 o C. Prior egssing ws rrie out using N 2 flow (40 ml min -1 ) t 160 C for 60 min in orer to tivte the smple n remove ny pture tmospheri CO 2. S28
29 Quntity sore (mmol g -1 ) NP-Imine-CO 2 t 273 K NP-Imizolium-CO 2 t 273 K NP-Imine-CO 2 t 298 K NP-Imizolium-CO 2 t 298 K NP-Imine-CO 2 t 323 K NP-Imizolium-CO 2 t 323 K Pressure (Br) Figure S25. CO 2 gs sorption n esorption isotherms of NP-Imine n NP-Imizolium mesure up to 1 r t 273, 298 n 323 K. Fille n empty symols represent sorption n esorption, respetively. S29
30 Setion 7. Ctlyti onversion of CO 2 to yli rontes on NP-NHC orgnotlyst y using epoxies Ctlyti tests. A 50 ml glss line stinless-steel retor equippe with mgneti stirring r n pressure ontroller ws hrge with NP-NHC tlyst (5 wt%) n the orresponing epoxie (5.0 mmol). The vessel ws pressurize with CO 2 (0.1 MP). After stirring for 24 h t 120 C, the retion ws stoppe y ooling the retor to room temperture. The retion mixture ws filtere off n wshe thoroughly with ry CH 2 Cl 2 to ensure omplete removl of the prout n ny unrete strting mterils from the pores of the NP-NHC orgnotlyst. The filtrte ws onentrte uner reue pressure n the rue smples were nlyze y 1H NMR spetrosopy. After eh yle, the tlyst ws sujete to 160 C heting uner vuum to remove ll the solvents n use it for the next yles. Figure S26. Plusile tlyti yle n retion pthwy for the formtion of yli rontes through tom eonomy retion etween CO 2 n epoxies tlyze y the NP-NHC. 5, 6 S30
31 Setion 8. Chrteriztion of yli rontes y 1 H NMR n gs hromtogrphy (GC) X X X X Figure S27. 1 H NMR (300 MHz, CDCl 3, 298 K) spetr of (±)-propylene oxie n its orresponing yli ronte ( 1 H NMR spetrum ws otine from the rue smple). S31
32 S32 Figure S28. 1 H NMR (300 MHz, CDCl 3, 298 K) spetrum of 1,2-epoxyhexne n its orresponing yli ronte ( 1 H NMR spetrum ws otine from the rue smple). f & f X g e g e X e,& e f f g g X
33 S33 Figure S29. 1 H NMR (300 MHz, CDCl 3, 298 K) spetrum of (±)-epihlorohyrin n its orresponing yli ronte ( 1 H NMR spetrum ws otine from the rue smple). X X X X X
34 Figure S30. 1 H NMR (300 MHz, CDCl 3, 298 K) spetrum of styrene oxie n its orresponing retion mixture ( 1 H NMR spetrum ws otine from the rue smple). S34
35 e e Figure S31. 1 H NMR (300 MHz, CDCl 3, 298 K) spetrum of epoxypropylene enzene n its orresponing retion mixture ( 1 H NMR spetrum ws otine from the rue smple). S35
36 Figure S32. Representtive GC t otine for propylene oxie n its orresponing yli ronte fter yloition of CO 2 over NP-NHC (Gs hromtogrm ws otine from the rue retion mixture). S36
37 Figure S33. Representtive GC t otine for epoxy hexne n its orresponing yli ronte fter yloition of CO 2 over NP-NHC (Gs hromtogrm ws otine from the rue retion mixture). S37
38 Figure S34. Representtive GC t otine for (±)-epihlorohyrin n its orresponing yli ronte fter yloition of CO 2 over NP-NHC (Gs hromtogrm ws otine from the rue retion mixture). S38
39 Retion mixture GC Figure S35. Representtive GC t otine for styrene oxie n its orresponing retion mixture fter yloition of CO 2 over NPNHC (Gs hromtogrm ws otine from the rue retion mixture). S39
40 Retion mixture GC Figure S36. Representtive GC t otine for 2,3-epoxy propyl enzene n its orresponing retion mixture fter yloition of CO 2 over NPNHC (Gs hromtogrm ws otine from the rue retion mixture). S40
41 Setion 9. Referenes 1. Jfrpour, L.; Stevens, E. D.; Noln, S. P., A sterilly emning nuleophili rene:1,3-is(2,6-iisopropylphenyl)imizol-2-yliene). Thermohemistry n tlyti pplition in olefin metthesis. J. Orgmet. Chem. 2000, 606, Lee, B. Y.; Kwon, H. Y.; Lee, S. Y.; N, S. J.; Hn, S.; Yun, H.; Lee, H.; Prk, Y.-W., Bimetlli nilio-limine zin omplexes for epoxie/co 2 opolymeriztion. J. Am. Chem. So. 2005, 127, Pney, P.; Frh, O. K.; Spokoyny, A. M.; Mirkin, C. A.; Kntziis, M. G.; Hupp, J. T.; Nguyen, S. T., A lik-se porous orgni polymer from tetrherl uiling loks. J. Mter. Chem. 2011, 21, Thiel, K.; Zehe, R.; Roeser, J.; Struh, P.; Enthler, S.; Thoms, A., A polymer nlogous retion for the formtion of imizolium n NHC se porous polymer networks. Polymer Chem. 2013, 4, Zhou, H.; Zhng, W.-Z.; Liu, C.-H.; Qu, J.-P.; Lu, X.-B., CO 2 uts of N-heteroyli renes: Therml stility n tlyti tivity towr the oupling of CO 2 with epoxies. J. Org. Chem. 2008, 73, Kyki, Y.; Ymmoto, M.; Ikriy, T., N-Heteroyli renes s effiient orgnotlysts for CO 2 fixtion retions. Angew. Chem. Int. E. 2009, 48, S41
A Straightforward Protocol for the Highly Efficient Preparation of. Main-chain Azo Polymers Directly from Bisnitroaromatic Compounds
Supporting Informtion A Strightforwr Protool for the Highly Effiient Preprtion of Min-hin Azo Polymers Diretly from Bisnitroromti Compouns y the Phototlyti Proess Liing Wng, Xingqing Pn, Yin Zho, Yng Chen,
More informationSupporting Information
Supporting Informtion Control Synthesis of Tuulr Hyperrosslinke Polymers for Highly Porous Cron Nnotues Xioyn Wng, Pn Mu, Chong Zhng, Yu Chen, Jinghui Zeng, Feng Wng n Ji-Xing Jing *, Shnxi Key Lortory
More informationSupporting Information Mesoporous graphitic carbon nanodisks fabricated via catalytic carbonization of coordination polymers
Supporting Informtion Mesoporous grphiti ron nnodisks frited vi tlyti roniztion of oordintion polymers Pnpn Su, Ling Jing, Jio Zho, Jingwng Yn, Cn Li nd Qihu Yng Stte Key Lortory of Ctlysis, Dlin Institute
More informationZSM-5 zeolite single crystals with b-axis-aligned mesoporous channels as an efficient catalyst for conversion of bulky organic molecules
Supporting informtion ZSM-5 zeolite single rystls with -xis-ligne mesoporous hnnels s n effiient tlyst for onversion of ulky orgni moleules Fujin Liu,,e Tom Willhmmr, Ling Wng, Longfeng Zhu, Qi Sun, Xingju
More information4-cyanopentanoic acid dithiobenzoate (CPADB) was synthesized as reported by Y.
Eletroni upplementry Mteril (EI) for Journl of Mterils Chemistry B This journl is The Royl oiety of Chemistry 2012 ynthesis of 4-ynopentnoi id dithioenzote (CPADB). 4-ynopentnoi id dithioenzote (CPADB)
More informationElectronic Supporting Information for
Eletroni Supplementry Mteril (ESI) for Polymer Chemistry. This journl is The Royl Soiety of Chemistry 2016 Eletroni Supporting Informtion for BODIPY Bse Hyperbrnhe Conjugte Polymers for Deteting Orgni
More information1 This diagram represents the energy change that occurs when a d electron in a transition metal ion is excited by visible light.
1 This igrm represents the energy hnge tht ours when eletron in trnsition metl ion is exite y visile light. Give the eqution tht reltes the energy hnge ΔE to the Plnk onstnt, h, n the frequeny, v, of the
More information6.3.2 Spectroscopy. N Goalby chemrevise.org 1 NO 2 CH 3. CH 3 C a. NMR spectroscopy. Different types of NMR
6.. Spetrosopy NMR spetrosopy Different types of NMR NMR spetrosopy involves intertion of mterils with the lowenergy rdiowve region of the eletromgneti spetrum NMR spetrosopy is the sme tehnology s tht
More informationAppendix A SYNTHESIS AND CHARACTERIZATION OF SIDE-GROUP LIQUID CRYSTAL POLYMERS
191 Appenix A SYNTHESIS AND CHARACTERIZATIN F SIDE-GRUP LIQUID CRYSTAL PLYMERS Appenix A...191 A.1 Appenix...191 A.2 Tles...197 A.3 Shemes...23 A.4 Figures...25 A.5 Referenes...23 A.1 Appenix All regents
More informationSupporting Information. M13 Virus-Incorporated Biotemplates on Electrode Surfaces to Nucleate Metal Nanostructures by Electrodeposition
Supporting Informtion M13 Virus-Inorported iotempltes on Eletrode Surfes to Nulete Metl Nnostrutures y Eletrodeposition Shnmugm Mnivnnn [], Inhk Kng [],, Yeji Seo [], Hyo-Eon Jin [,], Seung-Wuk Lee []
More informationTitle. CitationCatalysis Science & Technology, 2(8): Issue Date Doc URL. Rights. Type. Additional There Information
Title Remrkle enhnement of Cu tlyst tivity in hy Wng, Y-nn; Dun, Xinping; Zheng, Jinwei; Lin, H Author(s) Askur, Kiyotk CittionCtlysis Siene & Tehnology, 2(8): 1637-1639 Issue Dte 2012-08 Do URL http://hl.hnle.net/2115/52662
More informationH 4 H 8 N 2. Example 1 A compound is found to have an accurate relative formula mass of It is thought to be either CH 3.
. Spetrosopy Mss spetrosopy igh resolution mss spetrometry n e used to determine the moleulr formul of ompound from the urte mss of the moleulr ion For exmple, the following moleulr formuls ll hve rough
More information6.3.2 Spectroscopy. N Goalby chemrevise.org 1 NO 2 H 3 CH3 C. NMR spectroscopy. Different types of NMR
6.. Spetrosopy NMR spetrosopy Different types of NMR NMR spetrosopy involves intertion of mterils with the lowenergy rdiowve region of the eletromgneti spetrum NMR spetrosopy is the sme tehnology s tht
More informationERT 316: REACTION ENGINEERING CHAPTER 3 RATE LAWS & STOICHIOMETRY
ER 316: REIO EGIEERIG HER 3 RE LWS & SOIHIOMERY 1 OULIE R 1: Rte Lws Reltive Rtes of Retion Retion Orer & Rte Lw Retion Rte onstnt, k R 2: Stoihiometry th System Stoihiometri le low System Stoihiometri
More information3.15 NMR spectroscopy Different types of NMR There are two main types of NMR 1. C 13 NMR 2. H (proton) NMR
.5 NMR spetrosopy Different types of NMR There re two min types of NMR. NMR. (proton) NMR There is only round % in orgni moleules ut modern NMR mhines re sensitive enough to give full spetr for The spetr
More informationThe Department of Chemistry, Brown University, Providence, RI The Department of Chemistry, Yale University, New Haven, CT 06520
Eletroni Supplementry Mteril (ESI) for Chemil Siene. This journl is The Royl Soiety of Chemistry 2015 Supporting Informtion: Iron Ctlyzed CO 2 Hydrogention to Formte Enhned y Lewis Aid Co-Ctlysts Yunyun
More informationElectronic Supplementary Information
Electronic Supplementry Informtion Assemling cron-coted hollow α-fe 2 nnohorns on the CNT ckone for superior lithium storge cpility Corresponding uthor: Xiong Wen (Dvid) Lou* School of Chemicl nd Biomedicl
More informationAnalytical Techniques Chromatography
Anlytil Tehniques hromtogrphy hromtogrphy is n nlytil tehnique tht seprtes omponents in mixture etween moile phse nd sttionry phse. Types of hromtogrphy inlude: thin-lyer hromtogrphy (TL) plte is oted
More information22.Analytical Techniques Chromatography
.Anlytil Tehniques hromtogrphy hromtogrphy is n nlytil tehnique tht seprtes omponents in mixture etween moile phse nd sttionry phse. Types of hromtogrphy inlude: thin-lyer hromtogrphy (TL) plte is oted
More informationSupplemental Material
Supplementl Mteril Sulfmethzine Sorption to Soil: Vegettive Mngement, ph, nd Dissolved Orgni Mtter Effets Bei Chu, Keith W. Goyne *, Stephen H. Anderson, Chung-Ho Lin 2, nd Roert N. Lerh 3 Deprtment of
More informationAluminizing of Nickel-Based Superalloys Grade IN 738 by Powder Liquid Coating
Mterils Trnstions, Vol. 51, No. 5 (2010) pp. 982 to 987 #2010 The Jpn Institute of Metls Aluminizing of Nikel-Bse Superlloys Gre IN 738 y Power Liqui Coting Ptm Visuttipitukul 1; *, Nuntiy Limvnutpong
More informationElectronic supporting information
Eletroni supporting informtion Dully Ctioni n Anioni p/temperture-sensitive Injetle yrogels n Potentil Applition s Protein Crrier Cong Tru uynh, Minh Khnh guyen n Doo Sung Lee* 1. Experimentl 1.1. Mterils
More informationMorphology characterization. (a), SEM image of PS template nanospheres showing
b Supplementry Figure 1 Morphology chrcteriztion. (), SEM imge of PS templte nnospheres showing mono-dispersed sphericl shpe with pproximtely 200 nm in dimeter. The scle br is 500 nm. (b), SEM imge of
More informationSupplementary Information
Eletroni upplementry Mteril (EI) for Chemil Communitions This journl is The Royl oiety of Chemistry 0 Verstile Grfting Approhes to tr-hped P-Contining Hyrid Polymers using RAFT Polymeriztion nd Clik Chemistry
More informationHydrothermal saline promoted grafting: A new route to sulfonic acid SBA-15 silica with ultra-high acid site loading for biodiesel synthesis
Eletroni Supplementry Mteril (ESI) for Green Chemistry. This journl is The Royl Soiety of Chemistry 2014 yrotherml sline promote grfting: A new route to sulfoni i SBA-15 sili with ultr-high i site loing
More informationChemistry Practice Exam
Chemistry Prtie Exm 1 2 3 Whih of the following is n element? A rop of merury. A splinter of woo. A rystl of sugr. A rop of wter. Whih of the following nswers ontins only elements? Soium, soium hlorie,
More informationsupplementary information
DOI: 1.138/n2131 Protein levels (% of ) e Full-length protein remining (%) 1 5 1 5 1 1 5 5 Hs7 Syt1 Syt2 β-atin CSP +tsyn Hs7 Syt1 Syt2 P4 rin.1.1.1 1 [Trypsin] (g/l) f +tsyn SNARE-omplexes remining (%)
More informationThe Stirling Engine: The Heat Engine
Memoril University of Newfounln Deprtment of Physis n Physil Oenogrphy Physis 2053 Lortory he Stirling Engine: he Het Engine Do not ttempt to operte the engine without supervision. Introution Het engines
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Porous cationic polymers: The impact of counteranions and charges on CO 2 capture and conversion
More informationSupporting Information
Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,
More informationSupporting Information
Electronic Supplementry Mteril (ESI) for Nnoscle. This journl is The Royl Society of Chemistry Supporting Informtion A Dul-Emitting d-f Nnocrystlline Metl-Orgnic Frmework s Self- Clirting Luminescent Sensor
More informationSUPPLEMENTAL INFORMATION
SUPPLEMENTAL INFORMATION Evlution of Modified Boehm Titrtion Methods for Use with Lignoellulosi Biohrs Rivk B. Fidel, Dvid A. Lird*, Mihel L. Thompson Deprtment of Agronomy, Iow Stte University, Ames,
More information1 This question is about mean bond enthalpies and their use in the calculation of enthalpy changes.
1 This question is out men ond enthlpies nd their use in the lultion of enthlpy hnges. Define men ond enthlpy s pplied to hlorine. Explin why the enthlpy of tomistion of hlorine is extly hlf the men ond
More informationAppendix A: HVAC Equipment Efficiency Tables
Appenix A: HVAC Equipment Effiieny Tles Figure A.1 Resientil Centrl Air Conitioner FEMP Effiieny Reommention Prout Type Reommene Level Best Aville 11.0 or more EER 14.6 EER Split Systems 13.0 or more SEER
More informationLow temperature RAFT/MADIX gel polymerisation: access to controlled ultra-high molar mass polyacrylamides
Eletroni upplementry Mteril (EI) for Polymer Chemistry This journl is The Royl oiety of Chemistry 2014 Eletroni upplementry Informtion Low temperture RAFT/MADIX gel polymeristion: ess to ontrolled ultr-high
More informationAP CALCULUS Test #6: Unit #6 Basic Integration and Applications
AP CALCULUS Test #6: Unit #6 Bsi Integrtion nd Applitions A GRAPHING CALCULATOR IS REQUIRED FOR SOME PROBLEMS OR PARTS OF PROBLEMS IN THIS PART OF THE EXAMINATION. () The ext numeril vlue of the orret
More informationSupplementary Figures.
Supplementry Figures. c c Supplementry Figure 1 13 C NMR spectrum of representtive smple of PCPC in CDCl 3. The polymer ws purified y using DMS/MeH. CH 2 Cl 2 H 2 DMS Supplementry Figure 2 1 H NMR spectrum
More informationPoly(vinylamine) Microgels: ph-responsive Particles with High Primary Amine Contents
SUPPLEMENTARY INFORMATION Poly(vinylmine) Microgels: ph-responsive Prticles with High Primry Amine Contents Sineent Thioonro, Cory Berkln, Amir H. Milni, Rein Ulijn c n Brin R. Suners, * Polymer Science
More informationVISIBLE AND INFRARED ABSORPTION SPECTRA OF COVERING MATERIALS FOR SOLAR COLLECTORS
AGRICULTURAL ENGINEERING VISIBLE AND INFRARED ABSORPTION SPECTRA OF COVERING MATERIALS FOR SOLAR COLLECTORS Ltvi University of Agriulture E-mil: ilze.pelee@llu.lv Astrt Use of solr energy inreses every
More informationSupplementary Information
Supplementry Informtion Lignd exchnge triggered controlled-relese trgeted drug delivery system sed on core shell superprmgnetic mesoporous microspheres cpped with nnoprticles Zhogng Teng, Xingng Zhu, Gengfeng
More informationChapter 4rth LIQUIDS AND SOLIDS MCQs
Chpter 4rth LIQUIDS AND SOLIDS MCQs Q.1 Ioni solis re hrterize y () low melting points () goo onutivity in soli stte () high vpour pressure () soluility in polr solvents Q.2 Amorphous solis. () hve shrp
More informationConstruction of right-handed-, left-handed- and racemic helical. coordination polymers. Enantioselective recognition via chiral.
Construction of right-hnded-, left-hnded- nd rcemic helicl coordintion polymers. Enntioselective recognition vi chirl helicl crystls Kyung Hwn Prk, Te Hwn Noh, Yoon-Bo
More informationSynthesis, Characterization, and Polymerization of Sulfonamide Based Bifunctional Monomers
Synthesis, Chrteriztion, nd Polymeriztion of Sulfonmide Bsed Bifuntionl Monomers A thesis submitted in prtil fulfillment of the requirements for the degree of Mster of Siene By BRADY HALL B.S., The University
More informationUniversity of Sioux Falls. MAT204/205 Calculus I/II
University of Sioux Flls MAT204/205 Clulus I/II Conepts ddressed: Clulus Textook: Thoms Clulus, 11 th ed., Weir, Hss, Giordno 1. Use stndrd differentition nd integrtion tehniques. Differentition tehniques
More informationResearch Article Hydrothermal Synthesis of Ni/Al Layered Double Hydroxide Nanorods
Nnotehnology Volume 2011, Artile ID 646409, 6 pges doi:10.1155/2011/646409 Reserh Artile Hydrotherml Synthesis of Ni/Al Lyered Doule Hydroxide Nnorods Yun Zho, Fenfei Xio, nd Qingze Jio Shool of Chemil
More informationFirst compression (0-6.3 GPa) First decompression ( GPa) Second compression ( GPa) Second decompression (35.
0.9 First ompression (0-6.3 GP) First deompression (6.3-2.7 GP) Seond ompression (2.7-35.5 GP) Seond deompression (35.5-0 GP) V/V 0 0.7 0.5 0 5 10 15 20 25 30 35 P (GP) Supplementry Figure 1 Compression
More informationSupporting Information
tom-thik Interlyer Mde of VD-Grown Grphene Film on Seprtor for dvned thium-sulfur tteries Zhenzhen Du 1, hengkun Guo 2, njun Wng 3, jun Hu 1, Song Jin 1, Timing Zhng 1, Honghng Jin 1, Zhiki Qi 1, Sen Xin
More informationSilicon Nanowire Based Single-Molecule SERS Sensor
Supporting informtion Silicon Nnowire Bsed Single-Molecule SERS Sensor Hui Wng, Xuemei Hn, Xuemei Ou, Chun-Sing Lee, Xiohong Zhng* nd Shuit-Tong Lee S1, A series of Si nnowires coted with compct ggregtes
More informationThermodynamics. Question 1. Question 2. Question 3 3/10/2010. Practice Questions PV TR PV T R
/10/010 Question 1 1 mole of idel gs is rought to finl stte F y one of three proesses tht hve different initil sttes s shown in the figure. Wht is true for the temperture hnge etween initil nd finl sttes?
More informationSupporting Information
Supporting Informtion Ultrfst nd Stble CO Cpture Using Alkli Metl Slt-Promoted MgO-CCO 3 Sorbents Hongjie Cui, Qiming Zhng, Yunwu Hu, Chong Peng, Xingchen Fng, Zhenmin Cheng, Vldimir V. Glvit nd Zhiming
More informationSupplementary Information. High-Performance Mixed-Dimensional Perovskite Solar Cells with Enhanced
Eletroni Supplementry Mteril (ESI) for Journl of Mterils Chemistry A. This journl is The Royl Soiety of Chemistry 201 Supplementry Informtion High-Performne Mixed-Dimensionl Perovskite Solr Cells with
More informationSupporting Information
Supporting Informtion ICGM, ENSCM, Univ Montpellier, CNRS, 34296 Cedex 5, Montpellier, Frne L-LA monomer ws kindly gifted y Pur nd purified y stirring in dry diethyl ether followed y rerystlliztion in
More informationSupporting information
Electronic Supplementry Mteril (ESI) for Ctlysis Science & Technology. This journl is The Royl Society of Chemistry 2017 Supporting informtion PdAu imetllic nnoprticles nchored on mine-modified mesoporous
More informationCALCULATING REACTING QUANTITIES
MODULE 2 14 WORKSHEET WORKSHEET For multiple-hoie questions 1 5 irle the letter orresponding to the most orret nswer. 1 The lned eqution for the urning of utnol (C 4 H 9 OH) is given elow: C 4 H 9 OH(l)
More informationSynthesis of chiral 2-methyl-5,6,7,8-tetrahydroquinolines from naturally occurring monoterpenes
Generl Ppers ARKIVC 2004 (xiv) 44-50 Synthesis of hirl 2-methyl-5,6,7,8-tetrhydroquinolines from nturlly ourring monoterpenes Giorgio Chelui,* Ginmuro rrù, nd Frno Soolini Diprtimento di Chimi, Università
More informationElectronic Supplementary Information. Noninvasive Functionalization of Polymers of Intrinsic Microporosity for Enhanced CO 2 Capture
Electronic Supplementary Information Noninvasive Functionalization of Polymers of Intrinsic Microporosity for Enhanced CO 2 Capture Hasmukh A. Patel and Cafer T. Yavuz* Oxide and Organic Nanomaterials
More informationSynthesis of borinic acids and borinate adducts using diisopropylaminoborane
Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Ludovic Marciasini, Bastien Cacciuttolo, Michel Vaultier and Mathieu Pucheault* Institut des Sciences Moléculaires, UMR 5255,
More informationStraightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol
S1 Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2010 Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol Julien
More informationElectronic Supplementary Information
Electronic Supplementary Information General and highly active catalyst for mono and double Hiyama coupling reactions of unreactive aryl chlorides in water Dong-Hwan Lee, Ji-Young Jung, and Myung-Jong
More informationRed Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated
More informationCalix-Tris-Tröger s Bases A New Cavitand Family
Supplementry Mteril (ESI) for Chemicl Communictions This journl is (c) The Royl Society of Chemistry 200 Clix-Tris-Tröger s Bses A ew Cvitnd Fmily Mrtin Vlík, Jn Čejk, Mrtin vlík, Vldimír Král, Bohumil
More informationColorimetric detection and separation of chiral tyrosine. based on N-acetyl-L-cysteine modified gold. nanoparticles
Colorimetric detection nd seprtion of chirl tyrosine sed on N-cetyl-L-cysteine modified gold nnoprticles Hiyn Su, Qiuling Zheng nd Hiing Li* Key Lortory of Pesticide nd Chemicl Biology (CCNU), Ministry
More informationAn Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol
An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL
More informationSupporting Information
Supporting Information Towards Singlet Oxygen Delivery at a Measured Rate: A Selfreporting Photosensitizer Sundus Erbas-Cakmak #, Engin U. Akkaya # * # UNAM-National Nanotechnology Research Center, Bilkent
More informationChemical Equilibrium
Chpter 16 Questions 5, 7, 31, 33, 35, 43, 71 Chemil Equilibrium Exmples of Equilibrium Wter n exist simultneously in the gs nd liquid phse. The vpor pressure of H O t given temperture is property ssoited
More informationStructural Effect of Thioureas on the Detection of Chemical Warfare Agent Simulants
Structurl Effect of Thioures on the Detection of Chemicl Wrfre Agent Simulnts Seonggyun H, Minhe Lee, Hyun Ook Seo, b Sun Gu Song, Kyung-su Kim, Chn Heum Prk, Il Hee Kim, Young Dok Kim nd Chngsik Song*
More informationSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013 ph-controlled Reversible Formation of a Supramolecular Hyperbranched Polymer Showing Fluorescence Switching Bingran
More informationSupporting Information. (1S,8aS)-octahydroindolizidin-1-ol.
SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.
More informationSupporting Information
Supporting Information An efficient and general method for the Heck and Buchwald- Hartwig coupling reactions of aryl chlorides Dong-Hwan Lee, Abu Taher, Shahin Hossain and Myung-Jong Jin* Department of
More informationSynthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes
Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi
More informationEnhanced Photocatalytic CO 2 -Reduction Activity of Anatase TiO 2 by Coexposed {001} and {101} Facets
Supplementry Informtion for the Journl of Americn Chemicl Society The Americn Chemicl Society 04 Enhnced Photoctlytic CO -Reduction Activity of Antse TiO y Coexposed {00} nd {0} Fcets Jiguo Yu,*, Jingxing
More informationFacile Multistep Synthesis of Isotruxene and Isotruxenone
Facile Multistep Synthesis of Isotruxene and Isotruxenone Jye-Shane Yang*, Hsin-Hau Huang, and Shih-Hsun Lin Department of Chemistry, National Taiwan University, Taipei, Taiwan 10617 jsyang@ntu.edu.tw
More informationCEM143 MWF 8:00 8:50 am. October 5, 2018
CEM43, Fll 208 st Miterm CEM43 MWF 8:00 8:50 m st Miterm toer 5, 208 Nme: Setion: PID: TA: This is lose ook n note exmintion. This exm hs 35 questions. Answer ll questions on the seprte nswer sheet (ule
More informationCEM143 MWF 8:00 8:50 am. October 5, 2018
CEM43, Fll 208 st Miterm CEM43 MWF 8:00 8:50 m st Miterm toer 5, 208 Nme: Setion: PID: TA: This is lose ook n note exmintion. This exm hs 35 questions. Answer ll questions on the seprte nswer sheet (ule
More informationSupporting Information
Supporting Information Dynamic Crosslinking of Polymeric Binders Based on Host- Guest Interactions for Silicon Anodes in Lithium Ion Batteries Tae-woo Kwon,, You Kyeong Jeong,, Erhan Deniz, Siham Y. AlQaradawi,
More informationThermal energy 2 U Q W. 23 April The First Law of Thermodynamics. Or, if we want to obtain external work: The trick of using steam
April 08 Therml energy Soures of het Trnsport of het How to use het The First Lw of Thermoynmis U W Or, if we wnt to otin externl work: U W 009 vrije Universiteit msterm Close yle stem power plnt The trik
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 214 Supporting Information Lei Liu, ab Yijie Xia, b Jie Zhang* b a) China Center for Modernization
More informationDownloaded on T09:14:59Z
Title Investigtion of itive effets in enntioseletive opper-tlyse C- H insertion n romti ition retions of α-izoronyl ompouns Author(s) Slttery, Ctherine.; Clrke, Leslie-Ann; 'eill, Shne T.; Ring, Aoife;
More informationSUPPORTING INFORMATION
Dynamic covalent templated-synthesis of [c2]daisy chains. Altan Bozdemir, a Gokhan Barin, a Matthew E. Belowich, a Ashish. Basuray, a Florian Beuerle, a and J. Fraser Stoddart* ab a b Department of Chemistry,
More informationChem Homework 11 due Monday, Apr. 28, 2014, 2 PM
Chem 44 - Homework due ondy, pr. 8, 4, P.. . Put this in eq 8.4 terms: E m = m h /m e L for L=d The degenery in the ring system nd the inresed sping per level (4x bigger) mkes the sping between the HOO
More informationa) Read over steps (1)- (4) below and sketch the path of the cycle on a P V plot on the graph below. Label all appropriate points.
Prole 3: Crnot Cyle of n Idel Gs In this prole, the strting pressure P nd volue of n idel gs in stte, re given he rtio R = / > of the volues of the sttes nd is given Finlly onstnt γ = 5/3 is given You
More informationMomentum and Energy Review
Momentum n Energy Review Nme: Dte: 1. A 0.0600-kilogrm ll trveling t 60.0 meters per seon hits onrete wll. Wht spee must 0.0100-kilogrm ullet hve in orer to hit the wll with the sme mgnitue of momentum
More informationApplied. Grade 9 Assessment of Mathematics. Multiple-Choice Items. Winter 2005
Applie Gre 9 Assessment of Mthemtis Multiple-Choie Items Winter 2005 Plese note: The formt of these ooklets is slightly ifferent from tht use for the ssessment. The items themselves remin the sme. . Multiple-Choie
More informationBabak Karimi* and Majid Vafaeezadeh
Electronic upplementary Material (EI) for RC Advances This journal is The Royal ociety of Chemistry 2013 BA-15 functionalized sulfonic acid confined hydrophobic and acidic ionic liquid: a highly efficient
More informationH SERIES. Algebra Basics. Algebra Basics. Solutions. Curriculum Ready.
Alger Bsis H SERIES Alger Bsis Curriulum Rey www.mthletis.om Copyright 009 P Lerning. All rights reserve. First eition printe 009 in Austrli. A tlogue reor for this ook is ville from P Lerning Lt. ISBN
More informationElectronic Supplementary Information
Electronic Supplementary Information The directing effect of linking unit on building microporous architecture in tetraphenyladmantane-based poly(schiffbase) networks Guiyang Li, Biao Zhang, Jun Yan and
More informationChemical Equilibrium. Problem Set: Chapter 16 questions 25, 27, 33, 35, 43, 71
Chemil Equilibrium roblem Set: Chpter 16 questions 5, 7, 33, 35, 43, 71 Exmples of Equilibrium Wter n exists simultneously in the gs nd liquid phse. The vpor pressure of H O t given temperture is property
More informationLecture 6: Coding theory
Leture 6: Coing theory Biology 429 Crl Bergstrom Ferury 4, 2008 Soures: This leture loosely follows Cover n Thoms Chpter 5 n Yeung Chpter 3. As usul, some of the text n equtions re tken iretly from those
More informationSupporting Information
Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,
More informationSupporting Information for
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for
More informationSupporting Information
Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook
More informationSupporting Information. Vesicles of double hydrophilic pullulan and. poly(acrylamide) block copolymers: A combination
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information Vesicles of double hydrophilic pullulan and poly(acrylamide) block
More informationSTABILITY EVALUATI ON OF ph AND TEMPERATURE RESPONSIVE PARTICLES FROM STEADY-STATE RHEOLOGICAL MEASUREM ENTS
STABILITY EVALUATI ON OF ph AND TEMPERATURE RESPONSIVE PARTICLES FROM STEADY-STATE RHEOLOGICAL MEASUREM ENTS An M. S. Mi, Prisil S. Curti, Nívi N. Mrques, Rosngel C. Bln* Universie Feerl o Rio Grne o Norte
More informationSUPPLEMENTARY INFORMATION
Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some
More informationES-TA-3..1 Six- and Ten-Input E-Stop Safety Modules with DeviceNet
Emergeny Stop Sfety Moules Moel Seletion ES-TA-3..1 Six- n Ten-Input E-Stop Sfety Moules with DevieNet Sfety Moules s up to ten normlly lose emergeny stop swith iruits for ontt filure or wiring fult Diverse-reunnt
More information1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in
Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow
More informationExceptional Organic Solvents Uptake by Disulfide linked Polymeric. Networks
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Exceptional Organic Solvents Uptake by Disulfide linked
More informationSpacetime and the Quantum World Questions Fall 2010
Spetime nd the Quntum World Questions Fll 2010 1. Cliker Questions from Clss: (1) In toss of two die, wht is the proility tht the sum of the outomes is 6? () P (x 1 + x 2 = 6) = 1 36 - out 3% () P (x 1
More informationLight-Controlled Switching of a Non- Photoresponsive Molecular Shuttle
Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South
More informationCompounds and equations SAMPLE
USING CHEMISTRY 105 ACTIVITY 7.1 Litery Proessing n nlysing t n informtion Compouns n equtions Nming rules for ompouns When two or more elements hemilly join together, ompoun is forme. The nme of the ompoun
More information