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: 9 April 2020
Available Online: 19 April 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]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
2. [2]
  Ting-Ting Huang , Jin-Fa Chen , Juan Liu , Tai-Bao Wei , Hong Yao , Bingbing Shi , Qi Lin . A novel fused bi-macrocyclic host for sensitive detection of Cr₂O₇²⁻ based on enrichment effect. Chinese Chemical Letters, 2024, 35(7): 109281-. doi: 10.1016/j.cclet.2023.109281
3. [3]
  Dongsheng Yang , Zixin Li , Yaoyao Lian , Ziyao Fu , Tianjiao Li , Pengtao Ma , Guoping Yang . A novel square-shaped Zr-substituted polyoxotungstate for the efficient catalytic oxidation of sulfide to sulfone. Chinese Chemical Letters, 2025, 36(3): 109717-. doi: 10.1016/j.cclet.2024.109717
4. [4]
  Bin Zhao , Heping Luo , Jiaqing Liu , Sha Chen , Han Xu , Yu Liao , Xue Feng Lu , Yan Qing , Yiqiang Wu . S-doped carbonized wood fiber decorated with sulfide heterojunction-embedded S, N-doped carbon microleaf arrays for efficient high-current-density oxygen evolution. Chinese Chemical Letters, 2025, 36(5): 109919-. doi: 10.1016/j.cclet.2024.109919
5. [5]
  Caixia Zhu , Qing Hong , Kaiyuan Wang , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Single nanozyme-based colorimetric biosensor for dopamine with enhanced selectivity via reactivity of oxidation intermediates. Chinese Chemical Letters, 2024, 35(10): 109560-. doi: 10.1016/j.cclet.2024.109560
6. [6]
  Congyan Liu , Xueyao Zhou , Fei Ye , Bin Jiang , Bo Liu . Confined electric field in nano-sized channels of ionic porous framework towards unique adsorption selectivity. Chinese Chemical Letters, 2025, 36(2): 109969-. doi: 10.1016/j.cclet.2024.109969
7. [7]
  Zimo Yang , Yan Tong , Yongbo Liu , Qianlong Liu , Zhihao Ni , Yuna He , Yu Rao . Developing selective PI3K degraders to modulate both kinase and non-kinase functions. Chinese Chemical Letters, 2024, 35(11): 109577-. doi: 10.1016/j.cclet.2024.109577
8. [8]
  Runjing Xu , Xin Gao , Ya Chen , Xiaodong Chen , Lifeng Cui . Research status and prospect of rechargeable magnesium ion batteries cathode materials. Chinese Chemical Letters, 2024, 35(11): 109852-. doi: 10.1016/j.cclet.2024.109852
9. [9]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
10. [10]
  Junyi Yu , Yin Cheng , Anhong Cai , Xianfeng Huang , Qingrui Zhang . Synthetic Cu(Ⅲ) from copper plating wastewater for onsite decomplexation of Cu(Ⅱ)- and Ni(Ⅱ)-organic complexes. Chinese Chemical Letters, 2025, 36(2): 110549-. doi: 10.1016/j.cclet.2024.110549
11. [11]
  Weidan Meng , Yanbo Zhou , Yi Zhou . Green innovation unleashed: Harnessing tungsten-based nanomaterials for catalyzing solar-driven carbon dioxide conversion. Chinese Chemical Letters, 2025, 36(2): 109961-. doi: 10.1016/j.cclet.2024.109961
12. [12]
  Ying Wang , Hong Yang , Caixia Zhu , Qing Hong , Xuwen Cao , Kaiyuan Wang , Yuan Xu , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Cascading oxidoreductases-like nanozymes for high selective and sensitive fluorescent detection of ascorbic acid. Chinese Chemical Letters, 2025, 36(4): 110153-. doi: 10.1016/j.cclet.2024.110153
13. [13]
  Jie Yang , Xin-Yue Lou , Dihua Dai , Jingwei Shi , Ying-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818
14. [14]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
15. [15]
  Xueru Zhao , Aopu Wang , Shimin Wang , Zhijie Song , Li Ma , Li Shao . Adsorption and visual detection of nitro explosives by pillar[n]arenes-based host–guest interactions. Chinese Chemical Letters, 2025, 36(4): 110205-. doi: 10.1016/j.cclet.2024.110205
16. [16]
  Jingyu Chen , Sha Wu , Yuhao Wang , Jiong Zhou . Near-perfect separation of alicyclic ketones and alicyclic alcohols by nonporous adaptive crystals of perethylated pillar[5]arene and pillar[6]arene. Chinese Chemical Letters, 2025, 36(4): 110102-. doi: 10.1016/j.cclet.2024.110102
17. [17]
  Jianmei Guo , Yupeng Zhao , Lei Ma , Yongtao Wang . Ultra-long room temperature phosphorescence, intrinsic mechanisms and application based on host-guest doping systems. Chinese Journal of Structural Chemistry, 2024, 43(9): 100335-100335. doi: 10.1016/j.cjsc.2024.100335
18. [18]
  Cheng He , Renlan Huang , Lingling Wei , Qiuhui He , Jinbo Liu , Jiao Chen , Ge Gao , Cheng Yang , Wanhua Wu . Uncovering the mask of sensitizers to switch on the TTA-UC emission by supramolecular host-guest complexation. Chinese Chemical Letters, 2025, 36(4): 110103-. doi: 10.1016/j.cclet.2024.110103
19. [19]
  Lei Zhou , Youjun Zhou , Lizhen Fang , Yiqiao Bai , Yujia Meng , Liang Li , Jie Yang , Yong Yao . Pillar[5]arene based artificial light-harvesting supramolecular polymer for efficient and recyclable photocatalytic applications. Chinese Chemical Letters, 2024, 35(9): 109509-. doi: 10.1016/j.cclet.2024.109509
20. [20]
  Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . 表面硫物种对钯-硫纳米片加氢性能的影响. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-. doi: 10.3866/PKU.WHXB202309043

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1000)
HTML views(125)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142