Citation: 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[J]. Chinese Chemical Letters, ;2021, 32(1): 371-374. doi: 10.1016/j.cclet.2020.03.044 shu

Guest induced morphology transitions of star shaped pillar[5]arene trimer via endo host-guest and "exo-wall" electron-transfer interactions

Wajahat Ali ^a ,
Weitao Gong ^{a, *,} ,
Mehdi Hassan ^b ,
Weidong Qu ^a ,
Lu Liu ^a ,
Guiling Ning ^{a, *,}

a.
State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China
b.
Department of Chemistry University of Baltistan, Skardu, Pakistan

wtgong@dlut.edu.cn

ninggl@dlut.edu.cn

Received Date: 16 January 2020
Revised Date: 3 March 2020
Accepted Date: 16 March 2020
Available Online: 19 March 2020

Figures(9)

Star shape bridged pillar[5]arene trimer (C3-PLT) based on benzene-1,3,5-tricarboxamide (BTAs) was successfully synthesized, which exhibited outstanding guest responsive morphology transition properties. The morphology tuning studies was efficiently achieved with the addition of competitive guest molecules G1 and G2 by various self-assembly mechanisms. C3-PLT itself displays nanofiber morphology through H-type π-π stacking, and this nanofiber morphology can be completely transformed into spherical vesicles by host-guest interaction G1, while upon addition of G2 into C3-PLT by means of "exo-wall" electron-transfer interactions, sheet superstructures can be observed. SEM, ¹H NMR, DOSY, fluorescence spectroscopy, and viscosity have verified the formation of supramolecular polymers and morphological transitions between C3-PLT with both guests.
- Pillar[5]arene,
- Supramolecular polymers,
- Host-guest interactions
1. [1]
  X. Yan, J. Li, Chem. Soc. Rev. 39 (2010) 1877-1890. doi: 10.1039/b915765b
2. [2]
  X. Zhang, C. Dong, W. Huang, et al., Nanoscale 7 (2015) 16666-16670. doi: 10.1039/C5NR05213K
3. [3]
  Y. Zhou, D. Yan, Chem. Commun. (2009) 1172-1188.
4. [4]
  B.Y. Zhou, W. Huang, J. Liu, X. Zhu, D. Yan, Adv. Mater. 22 (2010) 4567-4590. doi: 10.1002/adma.201000369
5. [5]
  Z. Guo, Y. Zhang, W. Huang, Y. Zhou, D. Yan, Macromol. Rapid Commun. 29 (2008) 1746-1751. doi: 10.1002/marc.200800450
6. [6]
  W. Dong, Y. Zhou, D. Yan, Y. Liu, Phys. Chem. Chem. Phys. 9 (2007) 1255-1262. doi: 10.1039/b615525c
7. [7]
  R. Deng, M.J. Derry, C.J. Mable, Y. Ning, S.P. Armes, J. Am. Chem. Soc. 139 (2017) 7616-7623. doi: 10.1021/jacs.7b02642
8. [8]
  Y. Bai, C. Liu, D. Chen, et al., Beilstein J. Org. Chem. 15 (2019) 1925-1932. doi: 10.3762/bjoc.15.188
9. [9]
  D. Mandal, S.K. Mandal, M. Ghosh, P. Kumar, Chem. Eur. J. 21 (2015) 12042-12052. doi: 10.1002/chem.201501170
10. [10]
  C. Maity, W.E. Hendriksen, J.H. Van Esch, R. Eelkema, Angew. Chem. Int. Ed. 54 (2015) 998-1001. doi: 10.1002/anie.201409198
11. [11]
  A.T. Haedler, K. Kreger, A. Issac, et al., Nature 523 (2015) 196-199. doi: 10.1038/nature14570
12. [12]
  H. Jin, W. Huang, X. Zhu, Y. Zhou, D. Yan, Chem. Soc. Rev. 41 (2012) 5986-5997. doi: 10.1039/c2cs35130g
13. [13]
  J. Zhang, P.X. Ma, Angew. Chem. Int. Ed. 48 (2009) 964-968. doi: 10.1002/anie.200804135
14. [14]
  V.A. Online, Y. Yao, J. Li, et al., RSC Adv. 4 (2014) 9039-9043. doi: 10.1039/c3ra46681g
15. [15]
  B.C. Wang, Q. Chen, H. Xu, Z. Wang, X. Zhang, Adv. Mater. 22 (2010) 2553-2555. doi: 10.1002/adma.200904334
16. [16]
  P. Moitra, K. Kumar, P. Kondaiah, S. Bhattacharya, Angew. Chem. Int. Ed. 53 (2014) 1113-1117. doi: 10.1002/anie.201307247
17. [17]
  S. Fleming, R.V. Ulijn, Chem. Soc. Rev. 43 (2014) 8150-8177. doi: 10.1039/C4CS00247D
18. [18]
  G. Fichman, E. Gazit, Acta Biomater. 10 (2014) 1671-1682. doi: 10.1016/j.actbio.2013.08.013
19. [19]
  Y. Wang, N. Ma, Z. Wang, X. Zhang, Angew. Chem. Int. Ed. 46 (2007) 2823-2826. doi: 10.1002/anie.200604982
20. [20]
  T. Liu, S. Wang, Y. Song, J. Li, H. Yan, Polym. Chem. 8 (2017) 1306-1314. doi: 10.1039/C6PY02215D
21. [21]
  D. Ke, C. Zhan, A.D.Q. Li, J. Yao, Angew. Chem. Int. Ed. 50 (2011) 3715-3719. doi: 10.1002/anie.201006897
22. [22]
  S. Sun, M. Geng, L. Huang, et al., Chem. Commun. 54 (2018) 13006-13009. doi: 10.1039/C8CC07658H
23. [23]
  K.I. Anderson, R. Saunders, R.V. Ulijn, Biomater. Sci. 3 (2015) 246-249. doi: 10.1039/C4BM00297K
24. [24]
  G.M. Huurne, M.A.J. Gillissen, A.R.A. Palmans, I.K. Voets, E.W. Meijer, Macromolecules 40 (2015) 3949-3956.
25. [25]
  P. Van Der Schoot, E.W. Meijer, A.R.A. Palmans, Chem. Commun. 48 (2012) 3803-3805. doi: 10.1039/c2cc17284d
26. [26]
  H. Zhang, K.T. Nguyen, X. Ma, et al., Org. Biomol. Chem. 11 (2013) 2070-2074. doi: 10.1039/c2ob27340c
27. [27]
  T. Ogoshi, S. Kanai, S. Fujinami, T.A. Yamagishi, Y. Nakamoto, J. Am. Chem. Soc. 130 (2008) 5022-5023. doi: 10.1021/ja711260m
28. [28]
  Y. Liu, Y. Zhang, H. Zhu, et al., Mater. Chem. Front. 2 (2018) 1568-1573. doi: 10.1039/C8QM00220G
29. [29]
  J. Zhang, J. Zhu, C. Lu, et al., Polym. Chem. 7 (2016) 4317-4321. doi: 10.1039/C6PY00872K
30. [30]
  X. Wang, H. Deng, J. Li, et al., Macromol. Rapid Commun. 34 (2013) 1856-1862. doi: 10.1002/marc.201300731
31. [31]
  S. Sarkar, P. Choudhury, S. Dinda, P.K. Das, Langmuir 34 (2018) 10449-10468. doi: 10.1021/acs.langmuir.8b00259
32. [32]
  A. Ajayaghosh, C. Vijayakumar, R. Varghese, S.J. George, Angew. Chem. Int. Ed. 45 (2006) 456-460. doi: 10.1002/anie.200503258
33. [33]
  L. Brunsveld, J.A.J.M. Vekemans, J.H.K.K. Hirschberg, R.P. Sijbesma, E.W. Meijer, Proc. Natl. Acad. Sci. 99 (2002) 499-4982.
34. [34]
  X. Kuang, A. Wajahat, W. Gong, et al., Soft Matter 13 (2017) 4074-4079. doi: 10.1039/C7SM00642J
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]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
13. [13]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
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]
  Xianchen Hu , Junli Yang , Fang Gao , Zhiyong Zhao , Simin Liu . Highly selective [4+4] cross-photodimerization of (4a-azonia)anthracenes driven by confinement of D-A hetero-guest pair in cucurbit[10]uril host. Chinese Chemical Letters, 2025, 36(3): 109967-. doi: 10.1016/j.cclet.2024.109967
16. [16]
  Xiangjun Zhang , Xiaodi Yang , Yan Wang , Zhongping Xu , Sisi Yi , Tao Guo , Yue Liao , Xiyu Tang , Jianxiang Zhang , Ruibing Wang . A supramolecular nanoprodrug for prevention of gallstone formation. Chinese Chemical Letters, 2025, 36(2): 109854-. doi: 10.1016/j.cclet.2024.109854
17. [17]
  Zixu Xie , Pengfei Zhang , Ziyao Zhang , Chen Chen , Xing Wang . The choice of antimicrobial polymers: Hydrophilic or hydrophobic?. Chinese Chemical Letters, 2024, 35(9): 109768-. doi: 10.1016/j.cclet.2024.109768
18. [18]
  Hanying Li , Wee-Liat Ong . “Super-heterojunctioned” thermoelectric polymers. Chinese Chemical Letters, 2025, 36(2): 110523-. doi: 10.1016/j.cclet.2024.110523
19. [19]
  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
20. [20]
  Xiaoman Dang , Zhiying Wu , Tangxin Xiao , Zhouyu Wang , Leyong Wang . Highly robust supramolecular polymer networks crosslinked by metallacycles. Chinese Chemical Letters, 2024, 35(12): 110208-. doi: 10.1016/j.cclet.2024.110208

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(817)
HTML views(67)

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