Citation: Hui Qiang, Tao Chen, Zhuo Wang, Wenqian Li, Yunzhe Guo, Jie Yang, Xueshun Jia, Hui Yang, Weibo Hu, Ke Wen. Pillar[5]arene based conjugated macrocycle polymers with unique photocatalytic selectivity[J]. Chinese Chemical Letters, ;2020, 31(12): 3225-3229. doi: 10.1016/j.cclet.2020.04.020 shu

Pillar[5]arene based conjugated macrocycle polymers with unique photocatalytic selectivity

Hui Qiang ^{a, b} ,
Tao Chen ^{b, c} ,
Zhuo Wang ^d ,
Wenqian Li ^{b, c} ,
Yunzhe Guo ^{b, c} ,
Jie Yang ^d ,
Xueshun Jia ^a ,
Hui Yang ^b ,
Weibo Hu ^{b, *,} ,
Ke Wen ^{b, d, *,}

a.
College of Science, Shanghai University, Shanghai 200444, China
b.
Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201210, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China
d.
School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China

huwb@sari.ac.cn

wenk@sari.ac.cn

Received Date: 4 March 2020
Revised Date: 27 March 2020
Accepted Date: 27 March 2020
Available Online: 15 December 2020

Figures(3)

The development of heterogeneous catalysts with substrate shape, size or electronic constitution selectivity is a huge challenge in photocatalysis. Reported herein is a host-guest interaction strategy to endow photocatalysts with special selectivity. By adjusting the precursors, conjugated macrocycle polymers (CMPs) with pillar[5]arene struts (CMP-1 and CMP-2) and a corresponding non-pillar[5]arene-contained conjugated organic polymer (COP-1) were prepared and the photocatalytic activities toward sulfide derivatives were investigated. The sulfides showed similar conversions when COP-1 was used as a photocatalyst, but exhibited significant differences when it turned to the CMPs. Remarkably, the conversion yield of S-1 achieved near 18 folds over the one of S-2 when CMP-2 was used as a catalyst. Mechanism studies confirmed that the "host-guest" effect of pillar[5]arene struts in CMPs was the main cause of the difference. The present work establishes CMPs as novel heterogeneous photocatalysts with substrate selectivity, and such a method will inspire the researchers concerning preparation of heterogeneous catalysts with excellent selectivity.
- Heterogeneous photocatalysis,
- Selectivity,
- Host-guest,
- Pillar[5]arene,
- Sulfide
1. [1]
  W. Zhang, W.Z. Lai, R. Cao, Chem. Rev. 117(2017) 3717-3797. doi: 10.1021/acs.chemrev.6b00299
2. [2]
  P. Zhang, J.J. Zhang, J.L. Gong, Chem. Soc. Rev. 43(2014) 4395-4422. doi: 10.1039/C3CS60438A
3. [3]
  H.L. Dong, H.F. Zhu, Q. Meng, et al., Chem. Soc. Rev. 41(2012) 1754-1808. doi: 10.1039/C1CS15205J
4. [4]
  S.D. Xu, J.H. Tang, Q.W. Zhou, et al., ACS Sustainable Chem. Eng. 7(2019) 16190-16199. doi: 10.1021/acssuschemeng.9b03149
5. [5]
  Q. Liu, J.S. Dordick, C.Z. Dinu, ACS Appl. Mater. Interfaces 11(2019) 31049-31059. doi: 10.1021/acsami.9b10438
6. [6]
  M.F. Zheng, T. Yuan, J.L. Shi, et al., ACS Catal. 9(2019) 8068-8072. doi: 10.1021/acscatal.9b02550
7. [7]
  W.X. Huang, Z.L. Wu, J.W. Tang, et al., Chin. Chem. Lett. 29(2018) 725-726. doi: 10.1016/j.cclet.2018.05.021
8. [8]
  N. Yadav, F. Seidi, S. Del Gobbo, et al., Polym. Chem. 10(2019) 3571-3584. doi: 10.1039/C9PY00597H
9. [9]
  M.X. Wu, Y.W. Yang, Chin. Chem. Lett. 28(2017) 1135-1143. doi: 10.1016/j.cclet.2017.03.026
10. [10]
  I.C. Howard, C. Hammond, A. Buchard, Polym. Chem. 10(2019) 5894-5904. doi: 10.1039/C9PY01472A
11. [11]
  W. Zhu, X. Wang, T. Li, et al., Polym. Chem. 9(2018) 1430-1438. doi: 10.1039/C8PY00092A
12. [12]
  Y. Xu, T.Q. Wang, Z.D. He, et al., Polym. Chem. 9(2018) 4017-4024. doi: 10.1039/C8PY00694F
13. [13]
  J.L. White, M.F. Baruch, J.E. Pander, et al., Chem. Rev. 115(2015) 12888-12935. doi: 10.1021/acs.chemrev.5b00370
14. [14]
  Z.J. Wang, R. Li, K. Landfester, et al., Polymer 126(2017) 291-295. doi: 10.1016/j.polymer.2017.04.052
15. [15]
  L. Wang, W. Huang, R. Li, et al., Angew. Chem. Int. Ed. 55(2016) 9783-9787. doi: 10.1002/anie.201603789
16. [16]
  Y. Shiraishi, S. Kanazawa, Y. Kofuji, et al., Angew. Chem. Int. Ed. 53(2014) 13454-13459. doi: 10.1002/anie.201407938
17. [17]
  J.K. Liu, S.H. Wen, Y. Hou, et al., Angew. Chem. Int. Ed. 52(2013) 3241-3245. doi: 10.1002/anie.201209363
18. [18]
  Y.H. Fu, X.L. Zhu, L. Huang, et al., Appl. Catal. B:Environ. 239(2018) 46-51. doi: 10.1016/j.apcatb.2018.08.004
19. [19]
  L.M. Dai, Y.H. Xue, L.T. Qu, et al., Chem. Rev. 115(2015) 4823-4892. doi: 10.1021/cr5003563
20. [20]
  D.C. Wu, F. Xu, B. Sun, et al., Chem. Rev. 112(2012) 3959-4015. doi: 10.1021/cr200440z
21. [21]
  W.J. Zhang, J.T. Tang, W.G. Yu, et al., ACS Catal. 8(2018) 8084-8091. doi: 10.1021/acscatal.8b01478
22. [22]
  X.Y. Wang, L.J. Chen, S.Y. Chong, et al., Nat. Chem. 10(2018) 1180-1189. doi: 10.1038/s41557-018-0141-5
23. [23]
  V. Sadhasivam, M. Mariyappan, A. Siva, ChemistrySelect 3(2018) 13442-13455. doi: 10.1002/slct.201802977
24. [24]
  M. Zhang, W.D. Rouch, R.D. McCulla, Eur. J. Org. Chem. (2012) 6187-6196.
25. [25]
  B.C. Patra, S. Khilari, R.N. Manna, et al., Acs Catal. 7(2017) 6120-6127. doi: 10.1021/acscatal.7b01067
26. [26]
  Y. Zhou, Z.H. Xiang, D.P. Cao, et al., Ind. Eng. Chem. Res. 53(2014) 1359-1367. doi: 10.1021/ie403279y
27. [27]
  Z. Li, X. Li, Y.W. Yang, Small 15(2019) 1805509. doi: 10.1002/smll.201805509
28. [28]
  Y.J. Liang, J.L. Wei, X. Qiu, et al., Chem. Rev. 118(2018) 4912-4945. doi: 10.1021/acs.chemrev.7b00193
29. [29]
  M.K. Singh, D. Bandyopadhyay, J. Chem. Sci. 128(2016) 1-8. doi: 10.1007/s12039-015-0994-8
30. [30]
  M. Xu, C.L. Guo, H.Z. Dou, et al., Polym. Chem. 10(2019) 3786-3796. doi: 10.1039/C9PY00174C
31. [31]
  Z.H. Xiang, D.P. Cao, L.M. Dai, Polym. Chem. 6(2015) 1896-1911. doi: 10.1039/C4PY01383B
32. [32]
  C.R. Shugrue, S.J. Miller, Chem. Rev. 117(2017) 11894-11951. doi: 10.1021/acs.chemrev.7b00022
33. [33]
  S. Shoda, H. Uyama, J. Kadokawa, et al., Chem. Rev. 116(2016) 2307-2413. doi: 10.1021/acs.chemrev.5b00472
34. [34]
  Y. Zhao, Y.C. Huang, H. Zhu, et al., J. Am. Chem. Soc. 138(2016) 16645-16654. doi: 10.1021/jacs.6b07590
35. [35]
  D.C. Harris, X.Z. Chu, J. Jayawickramarajah, Supramol. Chem. 21(2009) 316-323. doi: 10.1080/10610270802549717
36. [36]
  J.i. Kadokawa, T. Shoji, K. Yamamoto, Catalysts 9(2019) 211. doi: 10.3390/catal9030211
37. [37]
  R. Ikura, J. Park, M. Osaki, et al., Macromolecules 52(2019) 6953-6962. doi: 10.1021/acs.macromol.9b01198
38. [38]
  C. Lescop, Acc. Chem. Res. 50(2017) 885-894. doi: 10.1021/acs.accounts.6b00624
39. [39]
  M.R. Patil, A.R. Kapdi, A.V. Kumar, ACS Sustainable Chem. Eng. 6(2018) 3264-3278. doi: 10.1021/acssuschemeng.7b03448
40. [40]
  J.H. Tang, Y. Li, Q. Wu, et al., Nat. Commun. 10(2019) 4599. doi: 10.1038/s41467-019-12534-6
41. [41]
  G.J. Qu, Y.P. Zhang, X. Ma, Chin. Chem. Lett. 30(2019) 1809-1814. doi: 10.1016/j.cclet.2019.07.042
42. [42]
  Y. Xu, M. von Delius, Angew. Chem. Int. Ed. 59(2020) 559-573. doi: 10.1002/anie.201906069
43. [43]
  W.B. Hu, C.D. Xie, W.J. Hu, et al., J. Org. Chem. 80(2015) 7994-8000. doi: 10.1021/acs.joc.5b01038
44. [44]
  G. Wang, H. Qiang, Y.Z. Guo, et al., Org. Biomol. Chem. 17(2019) 4600-4604. doi: 10.1039/C9OB00396G
45. [45]
  W.B. Hu, Z. Wang, X.L. Zhao, et al., Chem. Eur. J. 25(2019) 2189-2194.
46. [46]
  W.B. Hu, W.J. Hu, X.L. Zhao, et al., J. Org. Chem. 81(2016) 3877-3881. doi: 10.1021/acs.joc.6b00617
47. [47]
  W.B. Hu, H.M. Yang, W.J. Hu, et al., Chem. Commun. 50(2014) 10460-10463. doi: 10.1039/C4CC01810A
48. [48]
  B. Hua, W. Zhou, Z.L. Yang, et al., J. Am. Chem. Soc. 140(2018) 15651-15654. doi: 10.1021/jacs.8b11156
49. [49]
  U. Manna, G. Das, New J. Chem. 42(2018) 19164-19177. doi: 10.1039/C8NJ04457K
50. [50]
  D. Preston, K.F. White, J.E.M. Lewis, et al., Chem. Eur. J. 23(2017) 10559-10567. doi: 10.1002/chem.201701477
51. [51]
  N. Liu, K. Higashi, J. Kikuchi, et al., ., J. Phys. Chem. B 120(2016) 4496-4507. doi: 10.1021/acs.jpcb.6b00939
52. [52]
  L. Voorhaar, R. Hoogenboom, Chem. Soc. Rev. 45(2016) 4013-4031. doi: 10.1039/C6CS00130K
53. [53]
  X.F. Ji, D.Y. Xia, X.Z. Yan, et al., Acta Polym. Sinica (2017) 9-18.
54. [54]
  D.Y. Xia, P.F. Wei, B.B. Shi, et al., Chem. Commun. 52(2016) 513-516. doi: 10.1039/C5CC08038J
55. [55]
  Z.B. Zhang, Q. Zhao, J.Y. Yuan, et al., Chem. Commun. 50(2014) 2595-2597. doi: 10.1039/c3cc49108k
56. [56]
  E.R. Li, K.C. Jie, Y.J. Zhou, et al., J. Am. Chem. Soc. 140(2018) 15070-15079. doi: 10.1021/jacs.8b10192
57. [57]
  H. Zou, J. Liu, Y. Li, et al., Small 14(2018) 1802234. doi: 10.1002/smll.201802234
58. [58]
  Q.L. Li, Y. Sun, L. Ren, et al., ACS Appl. Mater. Interfaces 10(2018) 29314-29324. doi: 10.1021/acsami.8b09330
59. [59]
  Y.J. Choi, D.Y. Kim, M. Park, et al., ACS Appl. Mater. Interfaces 8(2016) 9490-9498. doi: 10.1021/acsami.6b03364
60. [60]
  D.R. Cao, H. Meier, Chin. Chem. Lett. 30(2019) 1758-1766. doi: 10.1016/j.cclet.2019.06.026
61. [61]
  X. Li, Z. Li, Y.W. Yang, Adv. Mater. 30(2018) 1800177. doi: 10.1002/adma.201800177
62. [62]
  A.I. Cooper, Adv. Mater. 21(2009) 1291-1295. doi: 10.1002/adma.200801971
63. [63]
  H. Zhang, Q. Huang, W.J. Zhang, et al., Chemphotochem 3(2019) 645-651.
64. [64]
  C.J. Li, K. Han, J. Li, et al., Org. Lett. 14(2012) 42-45. doi: 10.1021/ol2027834
65. [65]
  M.K. Dhinakaran, W.T. Gong, Y. Yin, et al., Polym. Chem. 8(2017) 5295-5302. doi: 10.1039/C7PY00845G
66. [66]
  T. Ogoshi, T. Kakuta, T.A. Yamagishi, Angew. Chem. Int. Ed. Engl. 58(2019) 2197-2206. doi: 10.1002/anie.201805884
1. [1]
  Cai-Li Sun , Jiang-Fei Xu , Yu-Zhe Chen , Li-Ya Niu , Li-Zhu Wua , Chen-Ho Tung , Qing-Zheng Yang . Monofunctionalized pillar[5]arene-based stable [1]pseudorotaxane. Chinese Chemical Letters, 2015, 26(7): 843-846. doi: 10.1016/j.cclet.2015.05.030
2. [2]
  Yufeng Cao , Yanmei Chen , Zhecheng Zhang , Jin Wang , Xiaolei Yuan , Qin Zhao , Yue Ding , Yong Yao . CO₂ and photo-controlled reversible conversion of supramolecular assemblies based on water soluble pillar[5]arene and coumarin-containing guest. Chinese Chemical Letters, 2021, 32(1): 349-352. doi: 10.1016/j.cclet.2020.03.058
3. [3]
  Shu Sun , Jian-Bing Shi , Yu-Ping Dong , Chen Lin , Xiao-Yu Hub , Le-Yong Wang . A pillar[5]arene-based side-chain pseudorotaxanes and polypseudorotaxanes as novel fluorescent sensors for the selective detection of halogen ions. Chinese Chemical Letters, 2013, 24(11): 987-992.
4. [4]
  Wajahat Ali , Weitao Gong , Mehdi Hassan , Weidong Qu , Lu Liu , Guiling Ning . Guest induced morphology transitions of star shaped pillar[5]arene trimer via endo host-guest and "exo-wall" electron-transfer interactions. Chinese Chemical Letters, 2021, 32(1): 371-374. doi: 10.1016/j.cclet.2020.03.044
5. [5]
  Chen Zhang , Xin Wen Guo , Ya Nan Wang , Xiang Sheng Wang , Chun Shan Song . Methylation of 2-methylnaphthalene with methanol to 2,6-dimethylnaphthalene over HZSM-5 modified by NH₄F and SrO. Chinese Chemical Letters, 2007, 18(10): 1281-1284. doi: 10.1016/j.cclet.2007.07.025
6. [6]
  Majdi Kacem , Gael Plantard , Nathalie Wery , Vincent Goetz . Kinetics and efficiency displayed by supported and suspended TiO₂ catalysts applied to the disinfection of Escherichia coli. Chinese Journal of Catalysis, 2014, 35(9): 1571-1577. doi: 10.1016/S1872-2067(14)60125-X
7. [7]
  Kai Lu , Wei Liu , Mei Ling Qi , Ruo Nong Fu . Retention behaviors of novel ionic liquid stationary phases and their selectivity for capillary gas chromatography. Chinese Chemical Letters, 2010, 21(12): 1475-1478. doi: 10.1016/j.cclet.2010.06.039
8. [8]
  Bo Yang , Yan Liu , Ming Li . Separation of CO₂–N₂ using zeolite NaKA with high selectivity. Chinese Chemical Letters, 2016, 27(6): 933-937. doi: 10.1016/j.cclet.2016.01.017
9. [9]
  Arash Ghorbani-Choghamarani , Mina Abbasi . Poly(4-vinylpyridinium tribromide) as metal-free,green and recoverable oxidizing polymer for the chemoselective oxidation of sulfides into sulfoxides. Chinese Chemical Letters, 2011, 22(1): 114-118. doi: 10.1016/j.cclet.2010.09.011
10. [10]
  Mehdi Bakavoli , Alireza Motavalizadeh Kakhky , Ali Shiri , Mahdieh Ghabdian , Abolghasem Davoodnia , Hossein Eshghi , Mola Khatami . Selective and mild oxidation of sulfides to sulfoxides by H₂O₂ using DBUH-Br₃ as catalyst. Chinese Chemical Letters, 2010, 21(6): 651-655. doi: 10.1016/j.cclet.2010.01.004
11. [11]
  Zhang Zibin , Sun Kechang , Li Shijun , Yu Guocan . A pillar[5]arene-based molecular grapple of hexafluorophosphate. Chinese Chemical Letters, 2019, 30(5): 957-960. doi: 10.1016/j.cclet.2019.01.018
12. [12]
  Sheng Yu , Yaqi Wang , Sobhan Chatterjee , Feng Liang , Fei Zhu , Haibing Li . Pillar[5]arene-functionalized nanochannel platform for detecting chiral drugs. Chinese Chemical Letters, 2021, 32(1): 179-183. doi: 10.1016/j.cclet.2020.11.055
13. [13]
  Chen Jian-Yu , Xiao Qi , Behera Harekrushna , Hou Jun-Li . Unimolecular artificial transmembrane channel with terminal dihydrogen phosphate groups showing transport selectivity for ammonium. Chinese Chemical Letters, 2020, 31(1): 77-80. doi: 10.1016/j.cclet.2019.05.009
14. [14]
  Wang Mengjun , Du Xusheng , Tian Huasheng , Jia Qiong , Deng Rong , Cui Yahan , Wang Chunyu , Meguellati Kamel . Design and synthesis of self-included pillar[5]arene-based bis-[1]rotaxanes. Chinese Chemical Letters, 2019, 30(2): 345-348. doi: 10.1016/j.cclet.2018.10.014
15. [15]
  Tianwei Cui , Guoxing Liu , Wenjing Zhang , Xinju Zhu , Juhua Leng , Xin-Qi Hao , Pu Mao , Mao-Ping Song . Metal-organic supramolecular nanoarchitectures by Ru(Ⅱ) bis-(terpyridine)-bridged pillar[5]arene dimers with triphenylamine. Chinese Chemical Letters, 2021, 32(1): 357-361. doi: 10.1016/j.cclet.2020.02.024
16. [16]
  Hui Chong , Cuiyun Nie , Lihong Wang , Sicong Wang , Ying Han , Yang Wang , Chengyin Wang , Chaoguo Yan . Construction and investigation of photo-switch property of azobenzene-bridged pillar[5]arene-based [3]rotaxanes. Chinese Chemical Letters, 2021, 32(1): 57-61. doi: 10.1016/j.cclet.2020.11.020
17. [17]
  Ye Junmei , Zhang Runmiao , Yang Wenjuan , Han Ying , Guo Hao , Xie Ju , Yan Chaoguo , Yao Yong . Pillar[5]arene-based[3]rotaxanes: Convenient construction via multicomponent reaction and pH responsive self-assembly in water. Chinese Chemical Letters, 2020, 31(6): 1550-1553. doi: 10.1016/j.cclet.2019.11.041
18. [18]
  Dana Bílková , Petr Jansa , Iva Paterová , Libor Červený . Hydrogenation of coumarin to octahydrocoumarin over a Ru/Ccatalyst. Chinese Journal of Catalysis, 2015, 36(7): 957-960. doi: 10.1016/S1872-2067(15)60860-9
19. [19]
  Hua Yang Zhao , Yi Ming Li , Tian Jun Gong , Qing Xiang Guo . A highly selective and easy-to-synthesize Zn(Ⅱ) fluorescent probe based on 6-methoxyquinolin. Chinese Chemical Letters, 2011, 22(9): 1013-1016. doi: 10.1016/j.cclet.2011.03.007
20. [20]
  Mao Zhong Tian , Feng Feng , Shuang Ming Meng , Yue Hua Yuan . A new selective fluorescent probe for lead ions. Chinese Chemical Letters, 2009, 20(3): 326-329. doi: 10.1016/j.cclet.2008.11.013

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