Citation: Jinjie Li, Huixian Jin, Zhikun Shang, Jie Wang, Donglai Tian, Yun Ding, Aiguo Hu. Synthesis of cycloparaphenylene under spatial nanoconfinement[J]. Chinese Chemical Letters, ;2023, 34(6): 107912. doi: 10.1016/j.cclet.2022.107912 shu

Synthesis of cycloparaphenylene under spatial nanoconfinement

Shanghai Key Laboratory of Advanced Polymeric Materials, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China

hagmhsn@ecust.edu.cn

Received Date: 6 September 2022
Revised Date: 8 October 2022
Accepted Date: 17 October 2022
Available Online: 19 October 2022

Figures(3)

Suzuki coupling reactions between symmetrical monomers were conducted in various mesoporous silica nanoreactors grafted with palladium catalysts, enabling the selective formation of [12]cycloparaphenylene precursor with separate yield up to 25% in one-pot reactions, much higher than that in homogeneous reaction. The spatial nanoconfinement of the nanoreactors promotes the macrocyclization while limits the concomitant linear oligomer formation, offering more possibilities for the synthesis of macrocycles from symmetrical monomers in one-pot reaction.
- Nanoreactor,
- Spatial confinement,
- Cyclization reaction,
- One-pot reaction,
- Suzuki coupling reaction
1. [1]
  G.M. Whitesides, M.E. Wilson, J. Am. Chem. Soc. 100 (1978) 306–307. doi: 10.1021/ja00469a064
2. [2]
  M. Jeschek, R. Reuter, T. Heinisch, C. Trindler, J. Klehr, S. Panke, T.R. Ward, Nature 537 (2016) 661–665. doi: 10.1038/nature19114
3. [3]
  M.T. Reetz, Acc. Chem. Res. 52 (2019) 336–344. doi: 10.1021/acs.accounts.8b00582
4. [4]
  S. Mosca, Y. Yu, J.V. Gavette, K.D. Zhang, J. Rebek, J. Am. Chem. Soc. 137 (2015) 14582–14585. doi: 10.1021/jacs.5b10028
5. [5]
  J.R. Donald, W.P. Unsworth, Chem. Eur. J. 23 (2017) 8780–8799. doi: 10.1002/chem.201700467
6. [6]
  Q. Shi, D. Masseroni, J. Rebek Jr., J. Am. Chem. Soc. 138 (2016) 10846–10848. doi: 10.1021/jacs.6b06950
7. [7]
  N.W. Wu, I.D. Petsalakis, G. Theodorakopoulos, Y. Yu, J. Rebek Jr., Angew. Chem. Int. Ed. 57 (2018) 15091–15095. doi: 10.1002/anie.201808265
8. [8]
  J.M. Yang, Y. Yu, J. Rebek Jr., J. Am. Chem. Soc. 143 (2021) 2190–2193. doi: 10.1021/jacs.0c12302
9. [9]
  F. Ziegler, J. Teske, I. Elser, et al., J. Am. Chem. Soc. 141 (2019) 19014–19022. doi: 10.1021/jacs.9b08776
10. [10]
  F. Ziegler, H. Kraus, M.J. Benedikter, et al., ACS Catal. 11 (2021) 11570–11578. doi: 10.1021/acscatal.1c03057
11. [11]
  S.T. Emmerling, F. Ziegler, F.R. Fischer, et al., Chem. Eur. J. 28 (2022) e202104108.
12. [12]
  H. Omachi, T. Nakayama, E. Takahashi, Y. Segawa, K. Itami, Nat. Chem. 5 (2013) 572–576. doi: 10.1038/nchem.1655
13. [13]
  R. Jasti, C.R. Bertozzi, Chem. Phys. Lett. 494 (2010) 1–7. doi: 10.1016/j.cplett.2010.04.067
14. [14]
  V. Parekh, P.J. Guha, Indian Chem. Soc. 11 (1934) 95–100.
15. [15]
  R. Jasti, J. Bhattacharjee, J.B. Neaton, C.R. Bertozzi, J. Am. Chem. Soc. 130 (2008) 17646–17647. doi: 10.1021/ja807126u
16. [16]
  K. Itami, Angew. Chem. Int. Ed. 48 (2009) 6112–6116. doi: 10.1002/anie.200902617
17. [17]
  Y. Ishii, Y. Nakanishi, H. Omachi, et al., Chem. Sci. 3 (2012) 2340–2345. doi: 10.1039/c2sc20343j
18. [18]
  F. Sibbel, K. Matsui, Y. Segawa, A. Studer, K. Itami, Chem. Commun. 50 (2014) 954–956. doi: 10.1039/C3CC48683D
19. [19]
  E.R. Darzi, T.J. Sisto, R. Jasti, J. Org. Chem. 77 (2012) 6624–6628. doi: 10.1021/jo3011667
20. [20]
  S. Deng, J. Zhi, X. Zhang, Q. Wu, Y. Ding, A. Hu, Angew. Chem. Int. Ed. 53 (2014) 14144–14148. doi: 10.1002/anie.201407387
21. [21]
  Y. Wu, M. Ding, J. Wang, et al., CCS Chem. 2 (2020) 64–70. doi: 10.31635/ccschem.020.202000126
22. [22]
  Y. Wu, J. Wang, Y. Zhu, et al., Chem. Commun. 57 (2021) 4146–4149. doi: 10.1039/D1CC00338K
23. [23]
  Y. Wu, Y. Zhu, J. Wang, et al., Chem. Eur. J. 28 (2022) e202102979. doi: 10.1002/chem.202102979
24. [24]
  J.M. Thomas, R. Raja, Acc. Chem. Res. 41 (2008) 708–720. doi: 10.1021/ar700217y
25. [25]
  K. Wang, J.H. Jordan, X.Y. Hu, L. Wang, Angew. Chem. Int. Ed. 59 (2020) 13712–13721. doi: 10.1002/anie.202000045
26. [26]
  U. Tallarek, J. Phys. Chem. C 122 (2018) 12350–12361. doi: 10.1021/acs.jpcc.8b03630
27. [27]
  L. Rossa, F. Vögtle, Top. Curr. Chem. 113 (1983) 1–86.
28. [28]
  M.R. Buchmeiser, ChemCatChem 13 (2021) 785–786. doi: 10.1002/cctc.202001941
1. [1]
  Jun Dong , Senyuan Tan , Sunbin Yang , Yalong Jiang , Ruxing Wang , Jian Ao , Zilun Chen , Chaohai Zhang , Qinyou An , Xiaoxing Zhang . Spatial confinement of free-standing graphene sponge enables excellent stability of conversion-type Fe₂O₃ anode for sodium storage. Chinese Chemical Letters, 2025, 36(3): 110010-. doi: 10.1016/j.cclet.2024.110010
2. [2]
  Cheng Cheng , Nasir Ali , Ji Liu , Juan Qiao , Ming Wang , Li Qi . Construction of degradable liposome-templated microporous metal-organic frameworks with commodious space for enzymes. Chinese Chemical Letters, 2024, 35(11): 109812-. doi: 10.1016/j.cclet.2024.109812
3. [3]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
4. [4]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
5. [5]
  Xuanyu Wang , Zhao Gao , Wei Tian . Supramolecular confinement effect enabling light-harvesting system for photocatalytic α-oxyamination reaction. Chinese Chemical Letters, 2024, 35(11): 109757-. doi: 10.1016/j.cclet.2024.109757
6. [6]
  Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
7. [7]
  Mengli Xu , Zhenmin Xu , Zhenfeng Bian . Achieving Ullmann coupling reaction via photothermal synergy with ultrafine Pd nanoclusters supported on mesoporous TiO2. Chinese Journal of Structural Chemistry, 2024, 43(7): 100305-100305. doi: 10.1016/j.cjsc.2024.100305
8. [8]
  Lu Dai , Yuxin Ren , Shuang Li , Meidi Wang , Chentao Hu , Ya-Pan Wu , Guangtong Hai , Dong-Sheng Li . Room-temperature synthesis of Co(OH)₂/Mo₂TiC₂T_x hetero-nanosheets with interfacial coupling for enhanced oxygen evolution reaction. Chinese Chemical Letters, 2025, 36(4): 109774-. doi: 10.1016/j.cclet.2024.109774
9. [9]
  Ren Shen , Yanmei Fang , Chunxiao Yang , Quande Wei , Pui-In Mak , Rui P. Martins , Yanwei Jia . UV-assisted ratiometric fluorescence sensor for one-pot visual detection of Salmonella. Chinese Chemical Letters, 2025, 36(4): 110143-. doi: 10.1016/j.cclet.2024.110143
10. [10]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
11. [11]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
12. [12]
  Tiantian Long , Hongmei Luo , Jingbo Sun , Fengniu Lu , Yi Chen , Dong Xu , Zhiqin Yuan . Carbonization-engineered ultrafast chemical reaction on nanointerface. Chinese Chemical Letters, 2025, 36(3): 109728-. doi: 10.1016/j.cclet.2024.109728
13. [13]
  Mengxing Liu , Jing Liu , Hongxing Zhang , Jianan Tao , Peiwen Fan , Xin Lv , Wei Guo . One-pot accessing of meso–aryl heptamethine indocyanine NIR fluorophores and potential application in developing dye-antibody conjugate for imaging tumor. Chinese Chemical Letters, 2025, 36(4): 109994-. doi: 10.1016/j.cclet.2024.109994
14. [14]
  Xuan Song , Teng Fu , Yajie Yang , Yahan Kuang , Xiuli Wang , Yu-Zhong Wang . Spatial-confinement combustion strategy enabling free radicals chemiluminescence direct-measurement in flame-retardant mechanism. Chinese Chemical Letters, 2025, 36(5): 110699-. doi: 10.1016/j.cclet.2024.110699
15. [15]
  Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
16. [16]
  Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
17. [17]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
18. [18]
  Zhao Li , Huimin Yang , Wenjing Cheng , Lin Tian . Recent progress of in situ/operando characterization techniques for electrocatalytic energy conversion reaction. Chinese Chemical Letters, 2024, 35(9): 109237-. doi: 10.1016/j.cclet.2023.109237
19. [19]
  Kunsong Hu , Yulong Zhang , Jiayi Zhu , Jinhua Mai , Gang Liu , Manoj Krishna Sugumar , Xinhua Liu , Feng Zhan , Rui Tan . Nano-engineered catalysts for high-performance oxygen reduction reaction. Chinese Chemical Letters, 2024, 35(10): 109423-. doi: 10.1016/j.cclet.2023.109423
20. [20]
  Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(542)
HTML views(43)

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