Citation: Yongjun Lv, Chao Xiao, Jingyu Ma, Dayang Zhou, Wanhua Wu, Cheng Yang. Solvent and guest-binding-controlled chiroptical inversion of molecular devices based on pseudo[1]catenane-type pillar[5]arene derivatives[J]. Chinese Chemical Letters, ;2024, 35(1): 108757. doi: 10.1016/j.cclet.2023.108757 shu

Solvent and guest-binding-controlled chiroptical inversion of molecular devices based on pseudo[1]catenane-type pillar[5]arene derivatives

Yongjun Lv ^{a, b, *,} ,
Chao Xiao ^{b, c} ,
Jingyu Ma ^b ,
Dayang Zhou ^d ,
Wanhua Wu ^b ,
Cheng Yang ^{b, *,}

a.
College of Chemical Engineering, Sichuan University of Science & Engineering, Zigong 643000, China
b.
College of Chemistry, Sichuan University, Chengdu 610064, China
c.
Zhejiang NHU Pharmeceutical Co., Ltd., Shaoxing 312000, China
d.
Comprehensive Analysis Center, ISIR, Osaka University, Osaka 567-0047, Japan

yongjunlv@qq.com

yangchengyc@scu.edu.cn

Received Date: 11 May 2023
Revised Date: 20 June 2023
Accepted Date: 29 June 2023
Available Online: 30 June 2023

Figures(8)

Four pillar[5]arene-based bicyclic compounds, so-called molecular universal joint (MUJ), were synthesized by incorporating a bisamide ring containing N, O, or S-heteroatom groups, which served as stimuli-responsive chiroptical molecular devices. The structure of MUJ was confirmed by ¹H NMR spectra and single-crystal X-ray diffraction analysis, and their planar-chiral enantiomers were successfully separated. Chiroptical inversion behaviors from in to out configurations triggered by temperature, solvent, and guest complexation were investigated by circular dichroism spectra. Chiroptical inversion could be realized in the presence of adiponitrile in certain solvents due to the solvation effects on the side ring and the threading of the guest into the pillar[5]arene cavity. However, the stronger self-included interactions between the cavity and the inside ring of certain MUJs led to inhibition of the switching.
- Pillar[5]arene,
- N,O,S-containg ring,
- Bicycles,
- Solvation,
- Chirality inversion
1. [1]
  L. Zhang, L. Qin, X. Wang, H. Cao, M. Liu, Adv. Mater. 26 (2015) 6959–6964.
2. [2]
  S. Sun, Y. Yang, D. Li, J. Zhu, J. Am. Chem. Soc. 141 (2019) 19524–19528. doi: 10.1021/jacs.9b08737
3. [3]
  L. Yao, K. Fu, X. Wang, et al., ACS. Nano 17 (2023) 2159–2169. doi: 10.1021/acsnano.2c08315
4. [4]
  P. Xing, Y. Li, Y. Wang, et al., Angew. Chem. Int. Ed. 57 (2018) 7774–7779. doi: 10.1002/anie.201802825
5. [5]
  C. Shi, H. Li, X. Shi, L. Zhao, H. Qiu, Chin. Chem. Lett. 33 (2022) 3613–3622. doi: 10.1016/j.cclet.2021.12.010
6. [6]
  F. Mamiya, N. Ousaka, E. Yashima, Angew. Chem. Int. Ed. 54 (2015) 14442–14446. doi: 10.1002/anie.201507918
7. [7]
  Y. Nagata, T. Yamada, T. Adachi, et al., J. Am. Chem. Soc. 135 (2013) 10104–10113. doi: 10.1021/ja403391m
8. [8]
  H.K. Bisoyi, Q. Li, Angew. Chem. Int. Ed. 55 (2016) 2994–3010. doi: 10.1002/anie.201505520
9. [9]
  J. Kim, J. Lee, W.Y. Kim, et al., Nat. Commun. 6 (2015) 6959–6964. doi: 10.1038/ncomms7959
10. [10]
  M. Liu, L. Zhang, T. Wang, Chem. Rev. 115 (2015) 7304–7397. doi: 10.1021/cr500671p
11. [11]
  H. Liang, B. Hua, F. Xu, et al., J. Am. Chem. Soc. 142 (2020) 19772–19778. doi: 10.1021/jacs.0c10570
12. [12]
  R. Lin, H. Zhang, S. Li, et al., Chem. Eur. J. 17 (2011) 2420–2427. doi: 10.1002/chem.201001867
13. [13]
  J. Gregolinski, M. Hikita, T. Sakamoto, et al., Inorg. Chem. 55 (2016) 633–643. doi: 10.1021/acs.inorgchem.5b01902
14. [14]
  E. Ohta, H. Sato, S. Ando, et al., Nat. Chem. 3 (2011) 68–73. doi: 10.1038/nchem.900
15. [15]
  J. Suk, V.R. Naidu, X. Liu, M.S. Lah, K.S. Jeong, J. Am. Chem. Soc. 133 (2011) 13938–13941. doi: 10.1021/ja206546b
16. [16]
  T. Ogoshi, D. Yamafuji, T. Akutsu, M. Naito, T.A. Yamagishi, Chem. Commun. 49 (2013) 8782–8784. doi: 10.1039/c3cc44672g
17. [17]
  E. Lee, H. Ju, I.H. Park, et al., J. Am. Chem. Soc. 140 (2018) 9669–9677. doi: 10.1021/jacs.8b05751
18. [18]
  K. Kato, S. Fa, S. Ohtani, et al., Chem. Soc. Rev. 51 (2022) 3648–3687. doi: 10.1039/d2cs00169a
19. [19]
  F. Gao, X. Yu, L. Liu, et al., Chin. Chem. Lett. 34 (2023) 107558–107561. doi: 10.1016/j.cclet.2022.05.072
20. [20]
  T. Ogoshi, T. Yamagishi, Y. Nakamoto, Chem. Rev. 116 (2015) 7937–8002.
21. [21]
  S. Fa, T. Kakuta, T. Yamagishi, T. Ogoshi, Chem. Let. 48 (2019) 1278–1287. doi: 10.1246/cl.190544
22. [22]
  A. Imayoshi, B.V. Lakshmi, Y. Ueda, T. Yoshimura, T. Kawabata, Nat. Commun. 12 (2021) 404. doi: 10.1038/s41467-020-20372-0
23. [23]
  J. Ye, L. Li, Y. You, et al., J. Am. Chem. Soc. 145 (2023) 384–390. doi: 10.1021/jacsau.2c00630
24. [24]
  H. Zhang, Z. Liu, F. Xin, Y. Zhao, Coord. Chem. Rev. 420 (2020) 213425–213433. doi: 10.1016/j.ccr.2020.213425
25. [25]
  C. Yan, Z. Zhang, Y. Ding, et al., Chin. Chem. Lett. 32 (2021) 1267–1279. doi: 10.3390/en14051267
26. [26]
  S. Yu, Y. Wang, S. Chatterjee, et al., Chin. Chem. Lett 32 (2021) 179–183. doi: 10.1016/j.cclet.2020.11.055
27. [27]
  L. Wu, C. Han, X. Jing, Y. Yao, Chin. Chem. Lett. 32 (2021) 3322–3330. doi: 10.1016/j.cclet.2021.04.046
28. [28]
  F. Lu, Y. Chen, B. Fu, S. Chen, L. Wang, Chin. Chem. Lett. 33 (2022) 5111–5115. doi: 10.1016/j.cclet.2022.03.103
29. [29]
  C. Liu, L. Zhou, S. Guo, H. Zhang, J. Han, Polym. Chem. 13 (2022) 286–299. doi: 10.1039/d1py01397a
30. [30]
  K. Wang, X. Tian, J.H. Jordan, et al., Chin. Chem. Lett. 33 (2022) 89–96. doi: 10.1016/j.cclet.2021.06.026
31. [31]
  H. Qiang, T. Chen, Z. Wang, et al., Chin. Chem. Lett. 31 (2020) 3225–3229. doi: 10.1016/j.cclet.2020.04.020
32. [32]
  J. Yao, W. Wu, W. Liang, Y. Feng, C. Yang, Angew. Chem. Int. Ed. 129 (2017) 6869–6873. doi: 10.1002/anie.201702542
33. [33]
  S. Fa, K. Adachi, Y. Nagata, et al., Chem. Sci. 12 (2021) 3483–3488. doi: 10.1039/d1sc00074h
34. [34]
  X. Yu, W. Wu, D. Zhou, et al., CCS Chem 4 (2022) 1806–1814. doi: 10.31635/ccschem.021.202101036
35. [35]
  Y. Zhou, G. Zhuang, P. Du, Chin. Chem. Lett. 34 (2023) 108593.
36. [36]
  D. Zhang, W. Liang, J. Yi, et al., Sci. China Chem. 65 (2022) 1149–1156. doi: 10.1007/s11426-022-1233-x
37. [37]
  J. Yao, W. Wu, C. Xiao, et al., Nat. Commun. 12 (2021) 2600. doi: 10.1038/s41467-021-22880-z
38. [38]
  J. Yao, H. Mizuno, C. Xiao, et al., Chem. Sci. 12 (2021) 4361–4366. doi: 10.1039/d0sc06988d
39. [39]
  C. Fan, J. Yao, G. Li, et al., Chem. Eur. J. 25 (2019) 12526–12537. doi: 10.1002/chem.201902676
40. [40]
  C. Xiao, W. Wu, W. Liang, et al., Angew. Chem., Int. Ed. 59 (2020) 8094–8098. doi: 10.1002/anie.201916285
41. [41]
  Y. Lv, C. Xiao, C. Yang, New. J. Chem. 42 (2018) 19357–19359. doi: 10.1039/c8nj04802a
42. [42]
  S.H. Li, H.Y. Zhang, X. Xu, Y. Liu, Nat. Commun. 6 (2015) 7590–7596. doi: 10.1038/ncomms8590
43. [43]
  G. Yu, B. Hua, C. Han, Org. Lett. 16 (2014) 2486–2489. doi: 10.1021/ol500857w
44. [44]
  N.L. Strutt, R.S. Forgan, J.M. Spruell, Y.Y. Botros, J.F. Stoddart, J. Am. Chem. Soc. 133 (2011) 5668–5671. doi: 10.1021/ja111418j
45. [45]
  L. Shao, Y. Pan, B. Hua, et al., Angew. Chem., Int. Ed. 59 (2020) 11779–11783. doi: 10.1002/anie.202000338
46. [46]
  G. Huang, W. Liu, A. Valkonen, et al., Chin. Chem. Lett. 29 (2018) 91–94. doi: 10.1016/j.cclet.2017.07.005
47. [47]
  C. Li, Q. Xu, J. Li, F. Yao, X. Jia, Org. Biomol. Chem. 8 (2010) 1568–1576. doi: 10.1039/b920146g
48. [48]
  X. Shu, S. Chen, J. Li, et al., Chem. Commun. 48 (2012) 2967–2969. doi: 10.1039/c2cc00153e
49. [49]
  C. Tu, W. Wu, W. Liang, et al., Angew. Chem. Int. Ed. 61 (2022) e202203541. doi: 10.1002/anie.202203541
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]
  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
4. [4]
  Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
5. [5]
  Qianqian Liu , Xing Du , Wanfei Li , Wei-Lin Dai , Bo Liu . Synergistic Effects of Internal Electric and Dipole Fields in SnNb₂O₆/Nitrogen-Enriched C₃N₅ S-Scheme Heterojunction for Boosting Photocatalytic Performance. Acta Physico-Chimica Sinica, 2024, 40(10): 2311016-. doi: 10.3866/PKU.WHXB202311016
6. [6]
  Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361
7. [7]
  Changjun You , Chunchun Wang , Mingjie Cai , Yanping Liu , Baikang Zhu , Shijie Li . 引入内建电场强化BiOBr/C₃N₅ S型异质结中光载流子分离以实现高效催化降解微污染物. Acta Physico-Chimica Sinica, 2024, 40(11): 2407014-. doi: 10.3866/PKU.WHXB202407014
8. [8]
  Kexin Dong , Chuqi Shen , Ruyu Yan , Yanping Liu , Chunqiang Zhuang , Shijie Li . Integration of Plasmonic Effect and S-Scheme Heterojunction into Ag/Ag₃PO₄/C₃N₅ Photocatalyst for Boosted Photocatalytic Levofloxacin Degradation. Acta Physico-Chimica Sinica, 2024, 40(10): 2310013-. doi: 10.3866/PKU.WHXB202310013
9. [9]
  Kaihui Huang , Boning Feng , Xinghua Wen , Lei Hao , Difa Xu , Guijie Liang , Rongchen Shen , Xin Li . Effective photocatalytic hydrogen evolution by Ti3C2-modified CdS synergized with N-doped C-coated Cu2O in S-scheme heterojunctions. Chinese Journal of Structural Chemistry, 2023, 42(12): 100204-100204. doi: 10.1016/j.cjsc.2023.100204
10. [10]
  Yatian Deng , Dao Wang , Jinglan Cheng , Yunkun Zhao , Zongbao Li , Chunyan Zang , Jian Li , Lichao Jia . A new popular transition metal-based catalyst: SmMn₂O₅ mullite-type oxide. Chinese Chemical Letters, 2024, 35(8): 109141-. doi: 10.1016/j.cclet.2023.109141
11. [11]
  Haohao Sun , Wenxuan Wang , Yuli Xiong , Zelang Jian , Wen Chen . Boosting the electrochromic properties by large V₂O₅ nanobelts interlayer spacing tuned via PEDOT. Chinese Chemical Letters, 2024, 35(9): 109213-. doi: 10.1016/j.cclet.2023.109213
12. [12]
  Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
13. [13]
  Ke Wang , Jia Wu , Shuyi Zheng , Shibin Yin . NiCo Alloy Nanoparticles Anchored on Mesoporous Mo2N Nanosheets as Efficient Catalysts for 5-Hydroxymethylfurfural Electrooxidation and Hydrogen Generation. Chinese Journal of Structural Chemistry, 2023, 42(10): 100104-100104. doi: 10.1016/j.cjsc.2023.100104
14. [14]
  Long TANG , Yaxin BIAN , Luyuan CHEN , Xiangyang HOU , Xiao WANG , Jijiang WANG . Syntheses, structures, and properties of three coordination polymers based on 5-ethylpyridine-2,3-dicarboxylic acid and N-containing ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1975-1985. doi: 10.11862/CJIC.20240180
15. [15]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
16. [16]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
17. [17]
  Zhixue Liu , Haiqi Chen , Lijuan Guo , Xinyao Sun , Zhi-Yuan Zhang , Junyi Chen , Ming Dong , Chunju Li . Luminescent terphen[3]arene sulfate-activated FRET assemblies for cell imaging. Chinese Chemical Letters, 2024, 35(9): 109666-. doi: 10.1016/j.cclet.2024.109666
18. [18]
  Aimin Fu , Chunmei Chen , Qin Li , Nanjin Ding , Jiaxin Dong , Yu Chen , Mengsha Wei , Weiguang Sun , Hucheng Zhu , Yonghui Zhang . Niduenes A−F, six functionalized sesterterpenoids with a pentacyclic 5/5/5/5/6 skeleton from endophytic fungus Aspergillus nidulans. Chinese Chemical Letters, 2024, 35(9): 109100-. doi: 10.1016/j.cclet.2023.109100
19. [19]
  Xiaoning Li , Quanyu Shi , Meng Li , Ningxin Song , Yumeng Xiao , Huining Xiao , Tony D. James , Lei Feng . Functionalization of cellulose carbon dots with different elements (N, B and S) for mercury ion detection and anti-counterfeit applications. Chinese Chemical Letters, 2024, 35(7): 109021-. doi: 10.1016/j.cclet.2023.109021
20. [20]
  Junmei FAN , Wei LIU , Ruitao ZHU , Chenxi QIN , Xiaoling LEI , Haotian WANG , Jiao WANG , Hongfei HAN . High sensitivity detection of baicalein by N, S co-doped carbon dots and their application in biofluids. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2009-2020. doi: 10.11862/CJIC.20240120

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(223)
HTML views(13)

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