Supporting Information. Reversible Light-Directed Red, Green and Blue Reflection with. Thermal Stability Enabled by a Self-Organized Helical
|
|
- Jeffery Clark
- 5 years ago
- Views:
Transcription
1 Supporting Information Reversible Light-Directed Red, Green and Blue Reflection with Thermal Stability Enabled by a Self-rganized Helical Superstructure Yannian Li, Augustine Urbas, and Quan Li *, Liquid Crystal Institute, Kent State University, Kent, hio 44242, United States Materials and Manufacturing Directorate, Air Force Research Laboratory WPAFB, hio 45433, United States * qli1@kent.edu Contents: 1. General Information. 2. Synthesis of Light-driven Dithienylethene Chiral Switches (S,S)-1 and (R,R)-1 3. Conformation Analysis of (S,S)-1 4. Photoisomerization and Spectra Data of (S,S)-1 in rganic Solvent. 5. Microscopic Textures and Pitch Changes Induced by Photoisomerization of (S,S)-1 in Nematic LC. 6. Measurement of Pitch and Helical Twisting Power. 7. References. 8. Copies of 1 H NMR and 13 C NMR SI1
2 1. General information All chemicals and solvents were purchased from commercial supplies and used without further purification. 1 H and 13 C NMR spectra were recorded on 400 or 200 MHz spectrometer in CDCl 3 or THF-d 8. Chemical shifts are in δ units (ppm) with the residual solvent peak or TMS as the internal standard. The coupling constant (J) is reported in hertz (Hz). NMR splitting patterns are designated as follows: s, singlet; d, doublet; t, triplet; and m, multiplet. Column chromatography was carried out on silica gel ( mesh). Analytical thin layer chromatography (TLC) was performed on commercially coated 60 mesh F 254 glass plates. Spots were rendered visible by exposing the plate to UV light. Melting points are uncorrected. Mass spectral data were measured with ESI ion mode. Textures and disclination line distance changes were observed by optical microscopy with temperature controller. UV-vis and Cicular dichroism (CD) spectra were collected at room temperature. The UV and visible light irradiation was carried out Xenon light source (100W) through a filter at 310 nm or 550 nm. Reflection spectra were measured with a spectrometer in the dark. The achiral nematic liquid crystals E7 and 5CB were commercially available. E7 is a eutectic mixture of LC components commercially designed for display applications and 5CB is 4 -pentyl-4-biphenylcarbonitrile (Figure S1). CN (5CB) 51% CN (7CB) 25% CN (8CB) 16% CN (5CT) 8% Figure S1. Chemical structures and composition of E7. SI2
3 2. Synthesis of light-driven axially chiral switches (S,S)-1 and (R,R)-1 Intermediate 2 was synthesis by a known procedure 1 and the characterization data were in accordance with the reference. Figure S2. Synthesis of intermediate 2. Intermediates (S)-4 and (R)-4 were synthesized starting from (S) and (R)-1,1 -Binaphthol in two steps, respectively. Figure S3. Synthesis of intermediates (S)-4 and (R)-4. The target compounds (S,S)-1 and (R,R)-1 were synthesized from 2 and (S)-4 or (R)-4 by a Suzuki coupling reaction, respectively. Figure S4. Synthesis of (S,S)-1 and (R,R)-1. SI3
4 (S)-2,2'- Methylenedioxy-1,1'-binaphthyl (S)-3 2 A mixture of (S)-1,1 -bi(2-naphthol) (1.43 g, 5 mmol), diiodomethane (4.01 g, 15 mmol) and anhydrous K 2 C 3 (4.14 g, 30 mmol) in acetone (50 ml) was stirred magnetically and refluxed until the reaction was complete as monitored by TLC. After cooling to room temperature, the reaction mixture was poured into water and extracted with ether (3 50 ml). The combined organic layer was washed with water, dried over Na 2 S 4 and concentrated. The crude product was purified by flash column chromatography over silica gel to give the product as white solid (1.37 g, 92%). Mp: o C. 1 H NMR (CDCl 3, 200 MHz) δ = (m, 4H), (m, 6H), (m, 2H), 5.70 (s, 2H). 13 C NMR (CDCl 3, 50 MHz) δ = 151.2, 132.2, 131.8, 130.3, 128.4, 126.9, , , 125.0, 120.9, HRMS (ESI) calcd for C 21 H 14 2 Na + : , found: (R)-2,2'-Methylenedioxy-1,1'-binaphthyl (R)-3 3 This intermediate was prepared by the same procedure as that used for (S)-3 from (R)-1,1 -bi(2-naphthol). The spectral data are the same as those for (S)-3. Mp: o C. HRMS (ESI) calcd for C 21 H 14 2 Na + : , found: SI4
5 I (S)-3-Iodo-2,2'-methylenedioxy-1,1'-binaphthyl (S)-4 To a THF solution (40 ml) of (S)-3 (596 mg, 2 mmol) at -78 o C under nitrogen was added t-buli (1.5 ml, 1.7 M in pentane, 2.5 mmol). The solution was stirred at this temperature for 1h. To the resulting solution was added a solution of I 2 (660 mg, 2.6 mmol) in THF (10 ml). The reaction mixture was allowed to warm to room temperature and stirred for an additional 10 h. The excess iodine was reduced with 1M Na 2 S 2 3. The reaction mixture was allowed to warm to room temperature, poured into water, and extracted with ethyl acetate (2 20 ml). The combined organic layers were dried over Na 2 S 4 and concentrated. The residue was purified by flash column chromatography to give the product as white solid (382 mg, 45%). Mp: o C. 1 H NMR (CDCl 3, 400 MHz) δ = 8.50 (s, 1H), 8.00 (d, J = 9.2 Hz, 1H), 7.94 (dd, J = 8.8, 1.2 Hz, 1H), 7.83 (d, J = 8.4 Hz, 1H), (m, 5H), (m, 2H), 5.71 (d, J = 3.6 Hz, 1H), 5.67 (d, J = 3.6 Hz, 1H). 13 C NMR (CDCl 3, 50 MHz) δ = 151.5, 149.3, 139.2, 133.1, 132.0, 131.7, 130.7, 128.4, 127.3, 127.0, 126.9, 126.7, 126.5, 126.2, 125.8, 125.1, 120.8, 102.6, Anal Calcd for C 21 H 13 I 2 : C, 59.45, H, 3.09; found: C, 59.22, H, HRMS (ESI) calcd for C 21 H 13 I 2 Na + : , found: I SI5
6 (R)-3-Iodo-2,2'-methylenedioxy-1,1'-binaphthyl (R)-4 This intermediate was prepared by the same procedure as that used for (S)-4 from (R)-3. The spectral data are the same as those for (S)-4. Mp: o C. Anal Calcd for C 21 H 13 I 2 : C, 59.45, H, 3.09; found: C, 59.19, H, HRMS (ESI) calcd for C 21 H 13 I 2 Na + : , found: Figure S5. Left: CD spectra of intermediates (S)-3 and (R)-3 (8 µm in hexane); Right: CD spectra of intermediates (S)-4 and (R)-4 (8 µm in hexane). S S (S,S)-1,2-Bis[2-methyl-5-(2,2'-methylenedioxy-1,1'-binaphthyl-3-yl)-3-thienyl] cyclopentene (S,S)-1 To a solution of 2 (164 mg, 0.5 mmol) in anhydrous THF (10 ml) was added n-buli (0.65 ml, 1.6 M in hexane, 1 mmol) dropwise, and the mixture was stirred at room temperature for 1h. Then B(Bu) 3 (345 mg, 1.5 mmol) was added and stirred at room temperature for another 1h followed by addition of (S)-4 (425 mg, 1 mmol), 20% Na 2 C 3 (8 ml) aqueous solution and Pd(PPh 3 ) 4 (35 mg, 0.03 mmol). The reaction SI6
7 mixture was heated and stirred for 10 h. After the mixture was cooled to room temperature, the organic layer was separated and the water layer was extracted with ethyl acetate (2 10 ml). The combined organic layers were washed dried over Na 2 S 4 and concentrated. The crude product was purified by flash column chromatography over silica gel to give the product as off-white solid (344 mg, 81%). Mp: o C. 1 H NMR (CDCl 3, 400 MHz) δ = 8.16 (s, 2H), 7.94 (d, J = 8.8 Hz, 2H), 7.93 (d, J = 8.0 Hz, 2H), 7.50 (d, J = 8.8 Hz, 2H), (m, 2H), (m, 8H), (m, 2H), (m, 2H), 5.59 (d, J = 3.6 Hz, 2H), 5.56 (d, J = 3.2 Hz, 2H), (m, 4H), (m, 2H), 2.13 (s, 6H). 13 C NMR (CDCl 3, 50 MHz) δ = 151.2, 147.6, 136.3, 136.0, 134.9, 134.1, 132.2, 131.7, 131.6, 131.1, 130.3, 128.4, 127.8, 127.4, 127.2, 126.9, 126.7, 126.2, 126.1, 125.8, 125.5, 125.0, 120.8, 102.4, 38.4, 23.1, Anal Calcd for C 57 H 40 4 S 2 : C, 80.25, H, 4.73; found: C, 80.27, H, HRMS (ESI) calcd for C 57 H 40 4 S 2 Na + : , found: S S (R,R)-1,2-Bis[2-methyl-5-(2,2'-methylenedioxy-1,1'-binaphthyl-3-yl)-3-thienyl] cyclopentene (R,R)-1 This compound was prepared by the same procedure as that used for (S,S)-1 from (R)-4. The spectral data are the same as those for (S,S)-1. Mp: o C. Anal Calcd SI7
8 for C 57 H 40 4 S 2 : C, 80.25, H, 4.73; found: C, 79.99, H, HRMS (ESI) calcd for C 57 H 40 4 S 2 Na + : , found: Conformation analysis of (S,S)-1 pen form θ~49 o Closed form θ~55 o Figure S6. ptimized structures and dihedral angels (θ) of (S,S)-1 at open form and closed form (Chem 3D, MM2 minimize energy, ball-stick model). 4. Photoisomerization and spectra data of (S,S)-1 in organic solvent SI8
9 Figure S7. 1 H NMR changes of light-driven chiral switch (S,S)-1 in THF-d 8 upon UV irradiation at 310 nm for different time. Absorbance Initial 5 s 15 s 25 s 40 s 60 s, PSS-UV A Wavelength (nm) PSS-UV 2 min B 5 min 7 min 10 min 15 min, PSS-Vis Wavelength (nm) Figure S8. UV-vis spectra changes of light-driven chiral switch (S,S)-1 (10 µm in hexane) upon UV irradiation at 310 nm (left) and upon visible light irradiation at 550 nm from PSS 310nm (right). Figure S9. Plot of absorbance at 550 nm of light-driven chiral switch (S,S)-1 in THF (20 µm) at room temperature: upon irradiation at 310 nm (left), then upon irradiation at 550 nm (right). 0.3 Absorbance Absorbance Cycles Time (days) Figure S10. Left: Cyclical absorbance of light-driven chiral switch (S,S)-1 (10 µm in hexane) at 553 nm as the solution was repeatedly irradiated with UV light (310 nm) SI9
10 for 1 min and then with visible light (550 nm) for 15 min. Right: Thermal stability of (S,S)-1 in dark at room temperature monitored by UV absorbance of 553 nm at PSS 310nm. 5. Microscopic textures and pitch changes induced by photoisomerization of (S,S)-1 in nematic liquid crystals Figure S11. Crossed polarized optical texture of 0.5 wt% (A and B) and 1.5 wt% (C and D) (S,S)-1 in E7 before (A and C) and after (B and D) UV irradiation at 310 nm. Figure S12. Change of distance (R) between Cano s lines of 1.0 wt% (S,S)-1 in E7 upon irradiation at 310 nm and visible light irradiation at 550 nm. 6. Measurement of pitch and helical twisting power A conventional technique for pitch measurement is Grandjean-Cano wedge method 4. Such wedge cell with an opening angle θ is made by applying two differently sized SI10
11 spacers at each end of the cell (Figure S13). If the alignment of the substrates is planar (the director lies parallel to the surface) and the rubbing directions of the substrates are parallel to one another, the cholesteric LC becones discrete. Because the value of the pitch is fixed, and the alignment is also fixed, the cholesteric LC arranges itself as in Figure S11. This arrangement produces disclination lines between areas that contain a different number of layers. The difference in thickness between each domain must be p/2 in order to satisfy the alignment boundary condition. The disclination lines of the cholesteric liquid crystal in the wedge cell can be seen through a polarizing optical microscope. The pitch was determined according to the equaton p=2r tanθ, where R represents the distance between the Grandjean lines and θ is the wedge angle of wedge cells (EHC, KCRK-07, tanθ = ). The inverse of pitch proportionally increases with increase in the concentration of a chiral dopant and HTP values is β = 1/(pc), where β is the helical twisting power, i.e, the ability of the chiral dopant to twist a nematic LC, and is the concentration of the chiral dopant. Figure S13. Schematic illustation of a Grandjean-Cano wedge cell for the pitch measurement of cholesteric LC. Disclination lines are pointed out with arrows and the thickness change between two domains is marked as p/2. The chiral nematic liquid crystal was prepared by weighing appropriate amount of host liquid crystal and the dopant into a vial followed by mixing them with the SI11
12 addition of a few drops of dichloromethane. After evaporation of the solvent under reduced pressure, the mixture was loaded into the wedge cell by capillary action at room temperature. The pitch was then determined by measuring the intervals of Cano s lines appearing on the surfaces of wedge-type liquid crystalline cells. Three different concentrations were used by this method for each sample, and the HTP were determined by plotting 1/p (µm -1 ) against concentration of the dopant c (mol%) according to the equation β = 1/(pc). Figure S14. Reciprocal helical pitch as a function of concentration of (S,S)-1 in nematic LC E7. 7. Reference: 1. (a) Lucas, L. N.; de Jong, J. J. D.; van Esch, J. H.; Kellogg, R. M.; Feringa, B. L. Eur. J. rg. Chem. 2003, (b) Akazawa, M.; Uchida, K.; de Jong, J. J. D.; Areephong, J.; Stuart, M.; Carili, G.; Browne, W. R.; Feringa, B. L. rg. Biomol. Chem. 2008, 6, van Es, J. J. G. S.; Biemans, H. A. M.; Meijer, E. W. Tetrahedron: Asymmetry 1997, 8, Simpson, J. E.; Daub, G. H.; Hayes, F. N. J. rg. Chem. 1973, 38, SI12
13 4. (a) Grandjean, F. C. R. Hebd. Seances Acad. Sci. 1921, 172, (b) Cano, R. Bull. Soc. Fr. Mineral. 1968, 91, (c) Heppke, G.; estreicher, F. Mol. Cryst. Liq. Cryst. 1978, 41, SI13
14 8. Copies of 1 H NMR and 13 C NMR 1 H NMR of intermediate 3: SI14
15 13 C NMR of intermediate 3: SI15
16 1 H NMR of intermediate 4: SI16
17 13 C NMR of intermediate 4: SI17
18 1 H NMR of (S, S)-1: SI18
19 13 C NMR of (S,S)-1: SI19
Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic
More informationSupporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S
Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS
More informationSupplementary information. Optically intensity-driven reversible photonic bandgaps in selforganized. helical superstructures with handedness inversion
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2017 Supplementary information ptically intensity-driven reversible photonic
More informationSupporting Information for
Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,
More informationChiral nematic organo-siloxane oligopodes based on an axially chiral binaphthalene core
Chiral nematic organo-siloxane oligopodes based on an axially chiral binaphthalene core Christopher P. J. Schubert, M. Gabriela Tamba and Georg, H. Mehl * Department of Chemistry, University of Hull, Hull,
More informationN-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic supplementary information for -Hydroxyphthalimide: a new photoredox catalyst for [4+1]
More informationDomino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,
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 informationCarbonylative Coupling of Allylic Acetates with. Arylboronic Acids
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Carbonylative Coupling of Allylic Acetates with Arylboronic Acids Wei Ma, a Ting Yu, Dong Xue,*
More informationTetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon
SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone
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 informationSupplementary Table S1: Response evaluation of FDA- approved drugs
SUPPLEMENTARY DATA, FIGURES AND TABLE BIOLOGICAL DATA Spheroids MARY-X size distribution, morphology and drug screening data Supplementary Figure S1: Spheroids MARY-X size distribution. Spheroid size was
More informationDepartment of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures
Supporting Information Low Temperature n-butyllithium-induced [3,3]-Sigmatropic Rearrangement/Electrophile Trapping Reactions of Allyl-1,1- Dichlorovinyl Ethers. Synthesis of - - and -lactones. Aaron Christopher
More informationSYNTHESIS OF A 3-THIOMANNOSIDE
Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,
More informationSupporting Information to
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2016 Supporting Information to Novel Planar Chiral Dopants with High Helical
More informationThe First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C
Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,
More informationSynthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity
Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic
More informationSupplementary Information
Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)
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 informationMolecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe
Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments
More informationSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,
More informationDivergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site of Acid Catalysts
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site
More informationSupporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline
Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Chunpu Li 1,2, Lei Zhang 2, Shuangjie Shu 2 and Hong Liu* 1,2 Address: 1 Department of Medicinal
More informationElectronic Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2012
Ring Expansion of Alkynyl Cyclopropanes to Highly substituted Cyclobutenes via a N-Sulfonyl-1,2,3-Triazole Intermediate Renhe Liu, Min Zhang, Gabrielle Winston-Mcerson, and Weiping Tang* School of armacy,
More informationRational design of light-directed dynamic spheres
Electronic Supplementary Information (ESI) Rational design of light-directed dynamic spheres Yumi Okui a and Mina Han* a,b a Department of Chemistry and Department of Electronic Chemistry Tokyo Institute
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 informationSupporting Information. Light-induced Wide Range Color Switching of Liquid Crystal. Blue Phase doped with Hydrogen-bonded Chiral Azobenzene.
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Light-induced Wide Range Color Switching of Liquid Crystal Blue Phase
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl
More informationEnantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supplementary Information Enantioselectivity switch in copper-catalyzed conjugate addition
More informationSupporting Information
ne-pot synthesis of pyrrolidino- and piperidinoquinolinones by three-component aza-diels Alder reactions of -arylimines with in situ generated cyclic enamides. Wenxue Zhang, Yisi Dai, Xuerui Wang, Wei
More informationSynthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain
rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry
More informationReactions. James C. Anderson,* Rachel H. Munday. School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK
Vinyl-dimethylphenylsilanes as Safety Catch Silanols in Fluoride free Palladium Catalysed Cross Coupling Reactions. James C. Anderson,* Rachel H. Munday School of Chemistry, University of Nottingham, Nottingham,
More informationSupporting Information
Supporting Information Nano CuFe 2 O 4 as a Magnetically Separable and Reusable Catalyst for the Synthesis of Diaryl / Aryl Alkyl Sulfides via Cross-Coupling Process under Ligand Free Conditions Kokkirala
More informationSupporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones
Supporting Information Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Marco Bandini,* Riccardo Sinisi, Achille Umani-Ronchi* Dipartimento di Chimica Organica G. Ciamician, Università
More informationSynthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition
Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition Sonia Amel Diab, Antje Hienzch, Cyril Lebargy, Stéphante Guillarme, Emmanuel fund
More informationSupporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany A Highly Enantioselective Brønsted Acid Catalyst for the Strecker Reaction Magnus Rueping, * Erli Sugiono and Cengiz Azap General: Unless otherwise
More informationPhotooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins
S1 Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins Antonia Kouridaki, Tamsyn Montagnon, Maria Tofi and Georgios Vassilikogiannakis* Department of
More informationSupporting Information
Supporting Information ACA: A Family of Fluorescent Probes that Bind and Stain Amyloid Plaques in Human Tissue Willy M. Chang, a Marianna Dakanali, a Christina C. Capule, a Christina J. Sigurdson, b Jerry
More informationBulletin of the Chemical Society of Japan
Supporting Information Bulletin of the Chemical Society of Japan Enantioselective Copper-Catalyzed 1,4-Addition of Dialkylzincs to Enones Followed by Trapping with Allyl Iodide Derivatives Kenjiro Kawamura,
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
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 214 Supporting Information Rapid and sensitive detection of acrylic acid using a novel fluorescence
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 informationSupplementary Material
10.1071/CH13324_AC CSIRO 2013 Australian Journal of Chemistry 2013, 66(12), 1570-1575 Supplementary Material A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination
More informationElectronic Supplementary Information for. A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective
Electronic Supplementary Information for A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective and Sensitive Detection of H 2 S: Synthesis, Spectra and Bioimaging Changyu Zhang, 1 Runyu Wang,
More informationHalogen bonded dimers and ribbons from the self-assembly of 3-halobenzophenones Patricia A. A. M. Vaz, João Rocha, Artur M. S. Silva and Samuel Guieu
Electronic Supplementary Material (ES) for CrystEngComm. This journal is The Royal Society of Chemistry 27 Halogen bonded dimers and ribbons from the self-assembly of -halobenzophenones Patricia A. A.
More informationDual Catalyst System provides the Shortest Pathway for l-menthol Synthesis
Chemical Communications Supporting Information Dual Catalyst System provides the Shortest Pathway for l-menthol Synthesis Hironori Maeda, Shinya Yamada, Hisanori Itoh, and Yoji Hori* Takasago International
More informationSupporting Information. DBU-Mediated Metal-Free Oxidative Cyanation of α-amino. Carbonyl Compounds: Using Molecular Oxygen as the Oxidant
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information DBU-Mediated Metal-Free Oxidative Cyanation of α-amino
More informationElectronic Supplementary Material
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly
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 informationEffect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted
More informationFast and Flexible Synthesis of Pantothenic Acid and CJ-15,801.
Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801. Alan L. Sewell a, Mathew V. J. Villa a, Mhairi Matheson a, William G. Whittingham b, Rodolfo Marquez a*. a) WestCHEM, School of Chemistry,
More informationSolvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols
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 informationEnantioselective Conjugate Addition of 3-Fluoro-Oxindoles to. Vinyl Sulfone: An Organocatalytic Access to Chiral. 3-Fluoro-3-Substituted Oxindoles
Enantioselective Conjugate Addition of 3-Fluoro-Oxindoles to Vinyl Sulfone: An Organocatalytic Access to Chiral 3-Fluoro-3-Substituted Oxindoles Xiaowei Dou and Yixin Lu * Department of Chemistry & Medicinal
More informationSupporting Information
Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy
More informationSupporting Information. Table of Contents. 1. General Notes Experimental Details 3-12
Supporting Information Table of Contents page 1. General Notes 2 2. Experimental Details 3-12 3. NMR Support for Timing of Claisen/Diels-Alder/Claisen 13 4. 1 H and 13 C NMR 14-37 General Notes All reagents
More informationEfficient Pd-Catalyzed Amination of Heteroaryl Halides
1 Efficient Pd-Catalyzed Amination of Heteroaryl Halides Mark D. Charles, Philip Schultz, Stephen L. Buchwald* Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 Supporting
More informationFormal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis
Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, and Hideo Kigoshi* Department of Chemistry,
More informationHalogen halogen interactions in diiodo-xylenes
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society
More informationhydroxyanthraquinones related to proisocrinins
Supporting Information for Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins Joyeeta Roy, Tanushree Mal, Supriti Jana and Dipakranjan Mal* Address: Department of Chemistry,
More informationA Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones. Jin-Quan Yu, a and E. J.
A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones Jin-Quan Yu, a and E. J. Corey b * a Department of Chemistry, Cambridge University, Cambridge CB2 1EW, United
More informationSupporting Information
Supporting Information Calix[4, 5]tetrolarenes: A New Family of Macrocycles Yossi Zafrani* and Yoram Cohen* School of Chemistry, The Sackler Faculty of Exact Sciences, Tel Aviv University, Ramat Aviv 69978,
More informationSUPPORTING INFORMATION
SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry
More informationEfficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene
Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene Seyoung Choi and Sangho Koo* Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea. E-mail:
More informationBrønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis
Supporting Information Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-iminoesters through Auto-Tandem Catalysis Azusa Kondoh, b and Masahiro Terada* a a Department of Chemistry, Graduate School
More informationSupporting Information
Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and
More informationElectronic Supplementary Information. An Ultrafast Surface-Bound Photo-active Molecular. Motor
This journal is The Royal Society of Chemistry and wner Societies 2013 Electronic Supplementary Information An Ultrafast Surface-Bound Photo-active Molecular Motor Jérôme Vachon, [a] Gregory T. Carroll,
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 informationBlock: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection
Electronic Supplementary Information (ESI) Luminogenic Materials Constructed from Tetraphenylethene Building Block: Synthesis, Aggregation-Induced Emission, Two-Photon Absorption, Light Refraction, and
More informationSupporting Information
Supporting Information for Cu-Mediated trifluoromethylation of benzyl, allyl and propargyl methanesulfonates with TMSCF 3 Xueliang Jiang 1 and Feng-Ling Qing* 1,2 Address: 1 Key Laboratory of Organofluorine
More informationSupporting Information
An Improved ynthesis of the Pyridine-Thiazole Cores of Thiopeptide Antibiotics Virender. Aulakh, Marco A. Ciufolini* Department of Chemistry, University of British Columbia 2036 Main Mall, Vancouver, BC
More informationLight irradiation experiments with coumarin [1]
Materials and instruments All the chemicals were purchased from commercial suppliers and used as received. Thin-layer chromatography (TLC) analysis was carried out on pre-coated silica plates. Column chromatography
More informationHow to build and race a fast nanocar Synthesis Information
How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,
More informationEfficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2MgCl 2 2LiCl ** Stefan H. Wunderlich and Paul Knochel*
Efficient Mono- and Bis-Functionalization of 3,6-Dichloropyridazine using (tmp) 2 Zn 2Mg 2 2Li ** Stefan H. Wunderlich and Paul Knochel* Ludwig Maximilians-Universität München, Department Chemie & Biochemie
More informationHighly stereocontrolled synthesis of trans-enediynes via
Supporting Information for Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes Tsutomu Konno*, Misato Kishi, and Takashi Ishihara Address: Department of Chemistry
More informationPreparation of Polythiophene Films Showing Optical Activity by Electrochemical Polymerisation in Cholesteric Liquid Crystal Containing Coumarine
International Letters of Chemistry, Physics and Astronomy Online: 2015-01-26 ISSN: 2299-3843, Vol. 46, pp 42-47 doi:10.18052/www.scipress.com/ilcpa.46.42 2015 SciPress Ltd., Switzerland Preparation of
More informationElectronic Supplementary Information (ESI)
Electronic Supplementary Information (ESI) A thin-layered chromatography plate prepared from naphthalimide-based receptor immobilized SiO 2 nanoparticles as a portable chemosensor and adsorbent for Pb
More informationAziridine in Polymers: A Strategy to Functionalize Polymers by Ring- Opening Reaction of Aziridine
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information (ESI) Aziridine in Polymers: A Strategy to Functionalize
More informationSupporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials
Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde
More informationSupporting Information. Cells. Mian Wang, Yanglei Yuan, Hongmei Wang* and Zhaohai Qin*
Electronic Supplementary Material (ESI) for Analyst. This journal is The Royal Society of Chemistry 2015 Supporting Information Fluorescent and Colorimetric Probe Containing Oxime-Ether for Pd 2+ in Pure
More informationSupporting Information
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry Supporting Information General Remarks Most of chemicals were purchased from Sigma-Aldrich, Strem,
More informationSupporting Information
Efficient Greenish Blue Electrochemiluminescence from Fluorene and Spirobifluorene Derivatives Federico Polo, *,, Fabio Rizzo, *, Manoel Veiga Gutierrez, Luisa De Cola, Silvio Quici Physikalisches Institut,
More informationPalladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles
Supporting Information for Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles Xiao-Li Lian, Zhi-Hui Ren, Yao-Yu
More informationElectronic Supplementary Information (12 pages)
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A C 2 -responsive pillar[5]arene: synthesis and self-assembly in water Kecheng Jie, Yong Yao, Xiaodong
More informationPoly(4-vinylimidazolium)s: A Highly Recyclable Organocatalyst Precursor for. Benzoin Condensation Reaction
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 24 Supporting Information Poly(4-vinylimidazolium)s: A Highly Recyclable rganocatalyst Precursor
More informationTriazabicyclodecene: an Effective Isotope. Exchange Catalyst in CDCl 3
Triazabicyclodecene: an Effective Isotope Exchange Catalyst in CDCl 3 Supporting Information Cyrille Sabot, Kanduluru Ananda Kumar, Cyril Antheaume, Charles Mioskowski*, Laboratoire de Synthèse Bio-rganique,
More informationAggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane
Electronic Supplementary Information (ESI) Aggregation-induced emission enhancement based on 11,11,12,12,-tetracyano-9,10-anthraquinodimethane Jie Liu, ab Qing Meng, a Xiaotao Zhang, a Xiuqiang Lu, a Ping
More informationSupporting Information. Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation. of Sulfoxonium Ylides. Xingwei Li*, Table of Contents
Supporting Information Rhodium(III)-Catalyzed Synthesis of Naphthols via C-H Activation of Sulfoxonium Ylides Youwei Xu,, Xifa Yang,, Xukai Zhou,, Lingheng Kong,, and Xingwei Li*, Dalian Institute of Chemical
More informationA fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media
Supplementary Information A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media Weiwei Wang and Quanrui Wang* Department of Chemistry,
More informationSUPPORTING INFORMATION. in the Synthesis of Fluorenones and ortho-arylated. Benzonitriles
SUPPRTING INFRMATIN Carbon-Hydrogen Bond Functionalization Approach in the Synthesis of Fluorenones and ortho-arylated Benzonitriles Dmitry Shabashov, Jesús R. Molina Maldonado and lafs Daugulis* Department
More informationSupporting Information for: Using a Lipase as a High Throughput Screening Method for Measuring the Enantiomeric. Excess of Allylic Acetates
Supporting Information for: Using a Lipase as a High Throughput Screening Method for Measuring the Enantiomeric Excess of Allylic Acetates M. Burak Onaran and Christopher T. Seto* Department of Chemistry,
More informationSupplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)
Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) A solution of propenyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and
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 informationCopper-Catalyzed Oxidative Cyclization of Carboxylic Acids
Copper-Catalyzed xidative Cyclization of Carboxylic Acids Supplementary material (51 pages) Shyam Sathyamoorthi and J. Du Bois * Department of Chemistry Stanford University Stanford, CA 94305-5080 General.
More informationSupplementary Information. Direct difunctionalization of alkynes with sulfinic acids and
Electronic upplementary Material (E) for RC Advances. This journal is The Royal ociety of Chemistry 204 upplementary nformation Direct difunctionalization of alkynes with sulfinic acids and melecular iodine:
More informationA Sumanene-based Aryne, Sumanyne
A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871
More informationYujuan Zhou, Kecheng Jie and Feihe Huang*
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 A redox-responsive selenium-containing pillar[5]arene-based macrocyclic amphiphile: synthesis,
More informationSupporting Information
Supporting Information Iridium-Catalyzed Highly Regioselective Azide-Ynamide Cycloaddition to Access 5-Amido-Fully-Substituted 1,2,3-Triazoles under Mild, Air, Aqueous and Bioorthogonal Conditions Wangze
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information for Chiral Brönsted Acid Catalyzed Asymmetric Baeyer-Villiger Reaction of 3-Substituted Cyclobutanones Using Aqueous
More informationSynthesis of Secondary and Tertiary Amine- Containing MOFs: C-N Bond Cleavage during MOF Synthesis
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 Supporting Information Synthesis of Secondary and Tertiary Amine- Containing MFs: C-N Bond
More information