Supporting Information

Electronic Supplementry Mteril (ESI) for Chemicl Science. This journl is The Royl Society of Chemistry 2015 Supporting Informtion Heterogeneous conversion of C 2 into cyclic crbontes t mbient pressure ctlyzed by ionotherml-derived mesomcroporous hierrchicl poly(ionic liquid)s Xiochen Wng, Yu Zhou, Zengjing Guo, Guojin Chen, Jing Li, Yuming Shi, Yngqing Liu, Jun Wng Stte Key Lbortory of Mterils-riented Chemicl Engineering, College of Chemistry nd Chemicl Engineering, njing Tech University (Former njing University of Technology), njing 209, Chin Corresponding uthor. Tel: +86-25-83172264, Fx: +86-25-83172261, E-mil: junwng@njtech.edu.cn (J. Wng) The uthors contributed eqully to this work. The detils of IR nd 13 C MR spectr As shown in the FT-IR spectr (Figure 2C), ll the smples s well s the bisvinylimidzolium slt [C 1 DVIM]Br exhibit very brod nd strong bnd t 3000-2850 cm -1 ttributble to stretching vibrtions of the C-H group. 1 The smples PDMBr-E, PDMBr-H nd PDMBr ll present the fetured bnds for imidzole ring t c. 1647 nd 1568 cm -1, evidencing the existence of the imidzolium moiety in the polyctionic frmework. 2,3, In ddition, the bnds round 962 cm -1 ttributed to the unsturted C-H vibrtions of vinyl groups re clerly observed on the spectrum of [C 1 DVIM]Br but disppers on the spectr of PDMBr-E, PDMBr-H nd PDMBr, suggesting the consuming of unrected vinyl groups. 4 The results demonstrte the successful polymeriztion of the bis-vinylimidzolium slt monomer with high polymeriztion degree. Besides, PDMBr-E, PDMBr-H nd PDMBr show similr spectr, indicting they hve the sme chemicl composition of the polymeric skeleton. Importntly, PDMBr prepred in IL [C 4 MIM]Br shows the similr spectr with PDMBr-E nd PDMBr-H, confirming the successful removl of IL solvent [C 4 MIM]Br from the polymer in the wshing step. 1

Figure 2D depicts the solid stte 13 C MR spectr of PDMBr-E, PDMBr-H nd PDMBr. Almost sme peks in 13 C MR spectr re observed over these three smples. The chemicl shift pek t pproximtely 42 ppm corresponds to terminl CH 2. The pek t round 55 ppm is ttributed to CH moiety nd the djcent pek t round 60 ppm corresponds to the methylene units linking the two imidzolium rings. The strong overlpping peks t round 125 ppm re scribed to the crbon toms of the C4 nd C5 toms in imidzolte ring. The C2 tom in the sme imidzolte ring is reflected by the single one t 138 ppm. 5 The lmost sme MR spectr over the smples PAMBr, PDMBr-E nd PDMBr-H further illustrte the sme chemicl frmework over these polymers, greeing with the results of FT-IR spectr. 2

A Br Br B Br Br Figure S1. (A) 1 H MR nd (B) 1 C MR of [C 1 DVIM]Br. 3

A BF 4 BF 4 B BF 4 BF 4 Figure S2. (A) 1 H MR nd (B) 1 C MR of [C 1 DVIM]BF 4. 4

A Br Br B Br Br Figure S3. (A) 1 H MR nd (B) 1 C MR of [C 2 DVIM]Br. 5

((A C 1s ((B 401.0 ev Intensity/.u. 1s 1s Br 3p3/2 Br 3s Br 3d5/2 Intensity (.u.) 800 600 400 200 0 Binding energy/ev 392 396 400 404 408 412 Binding Energy (ev) Figure S4. (A) Full XPS spectrum nd (B) the high resolution of 1s XPS spectrum for PAMBr. The peks corresponding to C 1s, 1s nd 1s cn be clerly observed in the XPS full spectrum, indicting tht the polyctionic chemicl components is crbon nd nitrogen, ccompnied by smll mount of oxygen come from the dsorbed wter (Figure S4A). The bromine element hs lso been detected in the XPS survey of PAMBr, reveling the existence of budunt bromine nion site in the polymer structure. 6 The high-resolution 1s XPS spectrum with the pek t 401.0 ev is ssigned to C- bonds in imidzolte ring (Figure S4B). 3 6

Percentge of weight/% 80 60 40 20 0 b c 200 300 400 500 600 700 Temperture/ o C Figure S5. TG curves of () PDMBr, (b) PDMBr-H nd (c) PDMBr-E. Intensity/.u. d c b 10 20 30 40 50 2 thet/degree Figure S6. XRD ptterns of () [C 1 DVIM]Br, (b) PDMBr, (c) PDMBr-H nd (d) PDMBr-E. 7

A Br B Br Figure S7. 1 H MR of (A) fresh [C 4 MIM]Br nd (B) recovered [C 4 MIM]Br. 8

A B C D E F Figure S8. SEM imges of the smples prepred with the initil mss composition of imidzolium slt monomer 0.3 g, [C 4 MIM]Br 6 g, H 2 0.75 g nd AIB 0.03 g. Imidzolium slt monomer: (A, B) [C 2 DVIM]Br; (C, D) [C 4 DVIM]Br; (E, F) [C 2 VIM]Br. 9

A B C D E F G H I Figure S9. SEM imges of the smples prepred with the initil mss composition of [C 1 DVIM]Br 0.3 g, IL 6 g, H 2 0.75 g nd AIB 0.03 g. IL: (A, B, C) [C 2 MIM]Br; (D, E, F) [C 6 MIM]Br; (G, H, I) [C 8 MIM]Br. 10

A B C D E F G H I Figure S10. SEM imges of the smples prepred with the initil mss composition of [C 1 DVIM]Br 0.3g, IL/ionic slt 6 g, H 2 0.75 g nd AIB 0.03 g. IL/ionic slt: (A, B, C) [P 4444 ]Br, (C, D, E) TPABr nd (F, G, H) TBABr. 11

50 = 145 m 2 g -1 0.02 Volume Adsorption/cm 3 g -1 b SBET = 222 m 2 g -1 c S = 260 BET m2 g -1 d = 181 m 2 g -1 e dv P /dd P /cm 3 g -1 b 0.01 c 0.01 d 0.02 e 40 = 55 m 2 g -1 0.002 0.0 0.2 0.4 0.6 0.8 1.0 P/P 0 1 10 Pore dimeter d P /nm Figure S11. 2 sorption isotherms (left) nd the corresponding pore size distribution curves (right) of the smples prepred with the initil mss composition of [C 1 DVIM]Br 0.3 g, IL 6 g nd H 2 0.75 g. IL/ionic slt: () [C 2 MIM]Br, (b) [C 6 MIM]Br, (c) TPABr, (d) TBABr nd (e) [P 4444 ]Br. 12

A B C D E F G H I J K L M P Q R Figure S12. SEM imges of the smples prepred with the initil mss composition of [C 1 DVIM]Br 0.3 g, [C 4 MIM]Br 6 g, H 2 x g nd AIB 0.03 g. (A, B, C) x=0; (D, E, F) x=0.25; (G, H, I) x=0.5; (J, K, L) x=1; (M,, ) x=1.5; (P, Q, R) x=2. 13

Volume Adsorption/cm 3 g -1 2 = 2 m 2 g -1 b = 147 m 2 g -1 c = 205 m 2 g -1 d = 189 m 2 g -1 e = 170 m 2 g -1 f S 25 BET = 62 m 2 g -1 0.0 0.2 0.4 0.6 0.8 1.0 P/P 0 dv P /dd P /cm 3 g -1 0.001 b 0.02 c 0.01 d 0.01 e 0.01 f 0.01 1 10 Pore dimeter d P /nm Figure S13. 2 sorption isotherms (left) nd the corresponding pore size distribution curves (right) of the smples prepred with the initil mss composition of [C 1 DVIM]Br 0.3 g, [C 4 MIM]Br 6 g, H 2 x g nd AIB 0.03 g. () x=0.25; (b) x= 0.5; (c) x= 0.75; (d) x= 1; (e) x= 1.5, nd (f) x= 2. = 219 m 2 g -1 0.02 Volume Adsorption/cm 3 g -1 b c d = 171 m 2 g -1 = 165 m 2 g -1 < 1 m 2 g -1 dv P /dd P /cm 3 g -1 0.01 b 0.01 c d 0.005 0.0 0.2 0.4 0.6 0.8 1.0 P/P 0 1 10 Pore dimeter d P /nm Figure S14. 2 sorption isotherms Reltive (left) pressure nd the corresponding (P/P 0 ) pore size distribution curves (right) of the smples prepred with the initil mss composition of [C 1 DVIM]Br 0.3 g, [C 4 MIM]Br x g, H 2 0.75 g nd AIB 0.03 g. () x=3, (b) x=2, (c) x=1 nd (d) x=0.5. 14

A B C D Figure S15. SEM imges of the smples prepred with the initil mss composition of [C 1 DVIM]Br 0.3g, [C 4 MIM]Br 6 g, co-solvent 0.75 g nd AIB 0.03 g. Co-solvent: (A, B) EtH; (C, D) DMS. 15

Volume Adsorption/cm 3 g -1 50 b c d e f 50 g 50 = 42 m 2 g -1 = 211m 2 g -1 = 224 m 2 g -1 = 190 m 2 g -1 = 156 m 2 g -1 = 62 m 2 g -1 = 57 m 2 g -1 0.0 0.2 0.4 0.6 0.8 1.0 P/P 0 dv P /dd P /cm 3 g -1 0.002 b 0.05 c 0.05 0.01 0.04 d e 0.01 0.01 f g 1 10 Pore dimeter d P /nm Figure S16. 2 sorption isotherms (left) nd the corresponding pore size distribution curves (right) of the smples with initil mss composition of [C 1 DVIM]BF 4 0.3g, [C 4 MIM]BF 4 6 g, co-solvent x g, nd AIB 0.03 g. H 2 is used s the co-solvent for () x=0, (b) x= 0.25, (c) x= 0.5, (d) x= 0.75, (e) x= 1. (f) 0.5 g DMF or (g) DMS is used s co-solvent. 16

Conversion/% 90 80 70 90 80 70 Selectivity/% Conversion (%) 80 60 80 60 Selectivity/% 60 60 40 90 110 120 130 0.0 0.5 1.0 1.5 2.0 Temperture/ o C Pressure/MP Figure S17. The effect of rection temperture nd pressure. Rection conditions: S (10 mmol), ctlyst PDMBr (0.05 g) nd rection time (4 h). 40 Conversion (%) Selectivity (%) 80 60 40 20 0 1 2 3 4 5 6 Run Figure S18. Ctlytic reusbility of PDMBr for cycloddition of C 2 to styrene oxide. Rection conditions: S 10 mmol, ctlyst PDMBr 0.05 g (1.3 mol%), C 2 pressure 1.0 MP, 110 C, 4 h. 17

Volume Adsorption/cm 3 g -1 400 300 200 A 0 0.0 0.2 0.4 0.6 0.8 1.0 P/P 0 dv P /dd P /cm 3 g -1 0.03 0.02 0.01 B 0.00 1 10 Pore dimeter d P /nm C D 5 μm 500 nm Figure S19. (A) 2 sorption isotherm, (B) pore size distribution curve nd (C, D) SEM imges of the recovered ctlyst PDMBr from cycloddition of C 2 to styrene oxide. Tble S1. Texturl properties of the smples prepred with the initil mss composition of [C 1 DVIM]Br 0.3 g, [C 4 MIM]Br 6 g, H 2 x g nd AIB 0.03 g. H 2 Entry (g) S BET V b p D c v (m 2 g -1 ) (cm 3 g -1 ) (nm) 1 d 0 - - - 2 0.25 2 0.01 14.3 3 0.5 147 0.32 8.7 4 0.75 205 0.57 11.0 5 1 189 0.51 10.6 6 1.5 170 0.44 10.3 7 2 62 0.14 9.2 8 e 0.75 197 0.59 12.1 9 f 0.75 12.0 0.08 26.0 10 g 0.75 11.5 0.06 21.6 BET surfce re. b Totl pore volume. c Averge pore dimeter. d Undetectble. e Recovered [C 4 MIM]Br is used s solvent. Initil mss composition: [C 1 DVIM]Br 0.3g, f DMF or g DMS 6 g, H 2 0.75 g nd AIB 0.03 g 18

Tble S2 The elementl nlysis dt of different smples. Elementl nlysis Clcd Elementl nlysis Found Smples C H C H C/ % % % % % % C/ [C 1 DVIM]Br 36.49 15.47 3.90 2.36 36.17 15.3 3.89 2.36 [C 1 DVIM]BF 35.15 14.91 3.75 2.36 34.90 14.85 3.536 2.35 PDMBr0.75 36.49 15.47 3.90 2.36 34.66 14.37 5.26 2.41 PDMBr-E 36.49 15.47 3.90 2.36 34.85 14.51 5.03 2.40 PDMBr-H 36.49 15.47 3.90 2.36 34.05 14.13 5.65 2.41 PDMBF 35.15 14.91 3.75 2.36 34.05 14.21 4.424 2.39 Tble S3 Texturl properties of the smples prepred with the initil mss composition of imidzolium slt monomer 0.3 g, [C 4 MIM]Br 6 g, H 2 0.75 g, nd AIB 0.03 g. Imidzolium slt Entry monomer S BET V b p D c v (m 2 g -1 ) (cm 3 g -1 ) (nm) 1 [C 1 DVIM]Br 205 0.57 11.0 2 [C 2 DVIM]Br 45 0.18 15.6 3 d [C 4 DVIM]Br - - - 4 d [C 2 VIM]Br - - - BET surfce re. b Totl pore volume. c Averge pore dimeter. d Undetectble. 19

Tble S4 Texturl properties of the smples prepred with the initil mss composition of [C 1 DVIM]Br 0.3 g, IL 6 g, H 2 0.75 g, nd AIB 0.03 g. Entry IL (m 2 g -1 ) V p b (cm 3 g -1 ) D v c (nm) 1 [C 2 MIM]Br 145 0.28 7.7 2 [C 4 MIM]Br 205 0.57 11.0 3 [C 6 MIM]Br 222 0.74 13.4 4 d [C 8 MIM]Br - - - 5 d [C 4 Py]Br - - - 6 [P 4444 ]Br 55 0.15 11.0 7 TPABr 260 0.62 9.6 8 TBABr 181 0.92 20.3 BET surfce re. b Totl pore volume. c Averge pore dimeter. d Undetectble. Tble S5 Texturl properties of the smples prepred with the initil mss composition of [C 1 DVIM]Br 0.3 g, [C 4 MIM]Br x g, H 2 0.75 g nd AIB 0.03 g. [C 4 MIM]Br Entry (g) S BET V b p D c v (m 2 g -1 ) (cm 3 g -1 ) (nm) 1 0.5 < 1 < 0.01 11.0 2 1 165 0.53 12.7 3 2 171 0.39 9.1 4 3 219 0.47 8.5 5 d 9 - - - BET surfce re. b Totl pore volume. c Averge pore dimeter. d Undetectble. 20

Tble S6 Texturl properties of the smples prepred with the initil mss composition of [C 1 DVIM]Br 0.3 g, [C 4 MIM]Br 6 g, cosolvent 0.75 g nd AIB 0.03 g. Entry Co-solvent (m 2 g -1 ) V p b (cm 3 g -1 ) D v c (nm) 1 EtH 4 0.01 8.9 2 AcH 10 0.05 17.5 3 DMF 7 0.03 16.7 4 DMS 10 0.05 19.2 BET surfce re. b Totl pore volume. c Averge pore dimeter. Tble S7. Texturl properties of the smples prepred with the initil mss composition of [C 1 DVIM]BF 4 0.3 g, [C 4 MIM]BF 4 6 g, co-solvent x g nd AIB 0.03 g. Entry Co-solvent/g S BET V b p D c v (m 2 g -1 ) (cm 3 g -1 ) (nm) 1 H 2 /0 42 0.2 20 2 H 2 /0.25 211 0.31 5.9 3 H 2 /0.5 224 0.40 7.2 4 H 2 /0.75 190 0.48 10.1 5 H 2 /1 156 0.37 9.5 6 DMF/0.5 62 0.17 11.2 7 DMS/0.5 57 0.18 12.2 BET surfce re. b Totl pore volume. c Averge pore dimeter. 21

Tble S8. Ctlytic ctivity of different poly(ionic liquid)s for cycloddition of C 2 to styrene oxide. Entry Ctlyst C 2 (MP) 1 Imidzolium-bsed polymeric ionic liquids Poly[vbim]Cl 5 140 24 67 [7] 2 Copolymeriztion of phosphorous ionic liquid PPIL-co-PEDMA 3 160 48 83.7 [8] 3 Phosphonium chlorides immobilized on fluorous polymer (homogeneous ctlyst) Temp. ( C) Time (h) Yield (%) Ref. 8 150 8 95 [9] 4 Silicon-bsed poly-imidzolium slts 1 110 2 96 [10] 5 Fluoro-functionlized PILs 1 120 9 96 [11] 6 Hydroxyl-functionlized PILs copolymer 2.5 130 6 90 [12] 7 Cross-linked-polymer-supported IL PVBIMCl 6 110 7 79.1 [13] 8 Mesoporous zwitterionic poly(ionic liquid)s 1 150 24 82 [14] 9 Chitosn functionlized ionic liquid CS-EMImBr 2 120 4 85 [15] 10 MCM-41-Imi/Br 3 4 97.7 [16] 11 12 Polymers nchored with crboxyl-functionlized di-ction ionic liquids Mesoporous polymer supported imidzolium-bsed ionic liquid FDU- HEIMBr 2.5 130 4 99.4 [17] 1 110 3 95 [18] 13 PDMBr 1 110 4 96.8 This work 22

Tble S9. Ctlytic ctivity of MF or microporous polymers for cycloddition of C 2 with epoxides under tmospheric pressure. Temp. Time Entry Ctlyst Co-ctlyst Epoxide Solvent ( C) (h) Yield (%) Ref. 1 PP-Br - DMF 90 70 80.4 [19] 2 MF-5 n-bu 4 Br - 50 15 92 [20] 3 Co-CMP n-bu 4 Br - 25 48 81.5 [21] 4 2D-CCB n-bu 4 Br 5 Hf-U-0 n-bu 4 Br - 12 91.1 [22] - 25 56 [23] 6 [SnIV(TH 2 PP)(Tf) 2 ]/CM-MIL-101 n-bu 4 PBr C 6 H 13 DMF 50 11 [24] 7 USTC-253-TFA n-bu 4 Br - 25 72 81.3 [25] 8 BIT-C n-bu 4 Br C 4 H 9-35 24 91 [26] 9 70 48 90.0 10 PDMBr - - 120 12 80.1 This work 11 C 12 H 25 120 48 97.1 23

Additionl explntion for Tbles S8 nd S9 nd ctivity comprison The comprison of ctlytic ctivities is difficult due to the vrition of the rection conditions (substrte, rection temperture, C 2 pressure, co-ctlyst, solvent, etc.) for different ctlysts. The comprison of the ctivity under the tmospheric pressure condition is especilly difficult becuse only severl reports re relted to the ctlytic performnces of heterogeneous ctlysts t such condition (Tble S9). Up to now, there is no report of heterogeneous ctlyst tht is ble to promote the cycloddition of C 2 to epoxides under mbient conditions without solvent or ddition of n externl homogeneous co-ctlyst. In this work, PDMBr is the first metl-solvent-dditive free recyclble heterogeneous ctlyst for cycloddition of C 2 under mbient conditions. Tble S9 lists the previous heterogeneous ctlysts for cycloddition of C 2 under different conditions. Quternry phosphonium-contining microporous polymer (PP-Br) gve the yield of 80.4% (90 C, 70 h) for the substrte of glycidyl phenyl ether when,dimethylformmide (DMF) ws used s the solvent (Tble S9, entry 1). By contrst, our synthesized PDMBr ctlyst exhibits the higher yield (90%) for the sme substrte t the lower temperture (70 C) nd shorter time (48 h) under the solvent-free condition, obviously demonstrting much higher ctivity thn PP-Br. In ddition, metl-orgnic frmeworks (MFs) or metl-coordinted conjugted microporous polymers (CMPs) in previous reports displyed efficient ctlytic ctivities for cycloddition of styrene oxide or propylene epoxide with C 2 into cyclic crbontes (1 tm, 25- C) (Tble S9, entry 2-6), but the homogeneous co-ctlysts like n-bu 4 Br or n-bu 4 PBr were needed to get those excellent results; otherwise, they presented inferior ctlytic performnce even t reltively high temperture nd C 2 pressure. 27-30 In other words, those ctlysts re short of specific bsic sites nd rely on the cidity of the metl cores within the frmework nd externl nucleophiles; 31,32 therefore, they themselves re unble to efficiently ctlyze the mbient cycloddition of C 2 to epoxides. The bove comprison llows drwing tht PDMBr of this work is more efficient heterogeneous ctlyst for cycloddition of C 2 to epoxides under mbient conditions. 24

For further insight into the present ctlyst PDMBr, it is lso evluted under the reltive mild conditions of 110 o C nd 1 MP, ccording to very recent reports. 10,18,32-35 Under such conditions, some previous heterogeneous ctlysts presented high ctivities, nonetheless, low yield ws observed over the inert substrtes like liphtic long crbon-chin lkyl epoxides, 10,15 nd decresed ctivity still occurred in recycling tests. 10,18,19 Generlly, styrene oxide is more rective thn long crbon-chin lkyl epoxides, but less rective thn those robust substrtes such s glycidyl ethers nd epichlorohydrin. In the erly studies (Tble S8, entry 1-3, 6, 7-11), the conversion of styrene oxide usully took plce t much higher temperture nd C 2 pressure with long rection time, wheres our PDMBr is more ctive, giving conversion of 99.0% nd selectivity of 98.5% t milder conditions. Compred with recently reported ones (Tble S8, entry 4, 5, 12), PDMBr lso exhibits better or t lest comprble ctivity, implying tht PDMBr is mong the most efficient IL-relted heterogeneous ctlysts for this rection. Further, other thn styrene oxide, PDMBr is ble to convert both the robust nd inert substrtes to corresponding cyclic crbontes with high yields under the reltive mild conditions of 110 o C nd 1 MP (Tble 2), which hs never been chieved before. An dditionl dvntge of PDMBr is its highly stble ctivity reveled by the recycling test. Bsed on bove nlysis, our obtined mteril PDMBr is n efficient ctlyst for C 2 conversion. It is the most efficient heterogeneous ctlyst under mbient conditions considering tht the high yields re chieved for vrious substrtes without ided by ny metls, dditives, nd solvents. References for Supporting Informtion [1] H. Chu, C. Yu, Y. Wn, D. Zho, J. Mter. Chem., 2009, 19, 8610-8618. [2] F. Liu, W. Li, Q. Sun, L. Zhu, X. Meng, Y.-H. Guo, F.-S. Xio, ChemSusChem, 2011, 4, 1059-1062. [3] G. Liu, M. Hou, J. Song, T. Jing, H. Fn, Z. Zhng, B. Hn, Green Chem., 2010, 12, 65-69. [4] L. Peng, J. Zhng, S. Yng, B. Hn, X. Sng, C. Liu, G. Yng, Chem. Commun., 2014, 50, 11957-11960. [5] H. Zho, L. Li, Y. Wng, R. Wng, Sci. Rep., 2014, 4, 5478. 25

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