Citation: Yuan-Tao Huang, Min Xue, Yong Yang. Imidazobenzimidazole fused aza-calix[4]arenes: Synthesis, structure, and Zn²⁺-selective colorimetric-fluorometric sensor[J]. Chinese Chemical Letters, ;2023, 34(12): 108294. doi: 10.1016/j.cclet.2023.108294 shu

Imidazobenzimidazole fused aza-calix[4]arenes: Synthesis, structure, and Zn²⁺-selective colorimetric-fluorometric sensor

Yuan-Tao Huang ^a ,
Min Xue ^b ,
Yong Yang ^{a, *,}

a.
Department of Chemistry, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, China
b.
Department of Physics, Key Laboratory of Optical Field Manipulation of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, China

yangyong@zstu.edu.cn

Received Date: 21 November 2022
Revised Date: 26 February 2023
Accepted Date: 1 March 2023
Available Online: 5 March 2023

Figures(6)

Tetra(amino)azacalix[4]arene skeleton was functionalized at the bridging NH sites using various aromatic aldehydes via formation of imidazobenzimidazole fused heterocycles. X-ray single crystal analysis revealed distorted 1,3-alternate conformations for the resulting macrocycles. Anthracenyl and pyrenyl modified imidazobenzimidazole fused aza-calix[4]arenes existed as dimers in the solid state, associated mainly through π-π stacking interactions between the planar polycyclic fluorophores. The tetrapyrenyl modified product was further used as a Zn²⁺-selective sensor, which showed naked-eye detected color change and enhanced excimer emission. The stoichiometry between the sensor and Zn²⁺ was determined to be 1:1 and the association constant was 1.1 × 10⁵ L/mol. The sensing process was highly selective and showed strong anti-interference with presence of other cations. The UV-vis spectral changes in the sensing process were completely reversible by alternate addition of Zn²⁺ and F⁻, showing an efficient ''on–off-on'' result.
- Aza-calix[4]arene,
- Imidazobenzimidazole,
- Fluorometric sensor,
- Zn²⁺-selective
1. [1]
  C.D. Gutsche, Calixarenes: An Introduction, 2nd Ed., RSC Pub., Cambridge, 2008.
2. [2]
  P. Neri, J.L. Sessler, M.X. Wang, Calixarenes and Beyond, Springer International Publishing, 2016.
3. [3]
  B. König, M.H. Fonseca, Eur. J. Inorg. Chem. (2000) 2303–2310.
4. [4]
  M.X. Wang, Acc. Chem. Res. 45 (2012) 182–195. doi: 10.1021/ar200108c
5. [5]
  N. Morohashi, F. Narumi, N. Iki, T. Hattori, S. Miyano, Chem. Rev. 106 (2006) 5291–5316. doi: 10.1021/cr050565j
6. [6]
  R. Kumar, Y.O. Lee, V. Bhalla, M. Kumar, J.S. Kim, Chem. Soc. Rev. 43 (2014) 4824–4870. doi: 10.1039/c4cs00068d
7. [7]
  W. Maes, W. Dehaen, Chem. Soc. Rev. 37 (2008) 2393–2402. doi: 10.1039/b718356a
8. [8]
  R. Hudson, J.L. Katz, Oxacalixarenes, in: P. Neri, J.L. Sessler, M.X. Wang (Eds.), Calixarenes and Beyond, Springer International Publishing, 2016, pp. 399–420.
9. [9]
  D.X. Wang, M.X. Wang, Azacalixaromatics, in: P. Neri, J.L. Sessler, M.X. Wang (Eds.), Calixarenes and Beyond, Springer International Publishing, 2016, pp. 363–398.
10. [10]
  H. Tsue, K. Ishibashi, R. Tamura, Top. Heterocycl. Chem. 17 (2008) 73–96.
11. [11]
  N. Sommer, H.A. Staab, Tetrahedron Lett. 7 (1966) 2837–2841. doi: 10.1016/S0040-4039(01)99870-3
12. [12]
  G.W. Smith, Nature 198 (1963) 879. doi: 10.1038/198879a0
13. [13]
  M.X. Wang, H.B. Yang, J. Am. Chem. Soc. 126 (2004) 15412–15422. doi: 10.1021/ja0465092
14. [14]
  J.L. Katz, M.B. Feldman, R.R. Conry, Org. Lett. 7 (2005) 91–94. doi: 10.1021/ol047840t
15. [15]
  J.L. Katz, K.J. Selby, R.R. Conry, Org. Lett. 7 (2005) 3505–3507. doi: 10.1021/ol051180q
16. [16]
  N. Kumar, P.X. Qui, I. Leray Roopa, M.H. Ha-Thi, Calixarene-based fluorescent molecular sensors, in: J.L. Atwood (Ed.), Comprehensive Supramolecular Chemistry Ⅱ, Elsevier B.V., 2017, pp. 197–226.
17. [17]
  R. Kumar, A. Sharma, H. Singh, et al., Chem. Rev. 119 (2019) 9657–9721. doi: 10.1021/acs.chemrev.8b00605
18. [18]
  A. Peterson, M.L. Ludvig, J. Martonova, et al., Supramol. Chem. 32 (2020) 313–319. doi: 10.1080/10610278.2019.1659269
19. [19]
  V. Mehta, M. Athar, P.C. Jha, et al., New J. Chem. 41 (2017) 5125–5132. doi: 10.1039/C7NJ01111C
20. [20]
  H.X. Wang, Z. Meng, J.F. Xiang, et al., Chem. Sci. 7 (2016) 469–474. doi: 10.1039/C5SC03511B
21. [21]
  M. Panchal, M. Athar, P.C. Jha, et al., RSC Adv. 6 (2016) 53573–53577. doi: 10.1039/C6RA05707A
22. [22]
  G. Canard, J.A. Edzang, Z. Chen, et al., Chem. Eur. J. 22 (2016) 5756–5766. doi: 10.1002/chem.201505089
23. [23]
  Y. Bansal, O. Silakari, Bioorg. Med. Chem. 20 (2012) 6208–6236. doi: 10.1016/j.bmc.2012.09.013
24. [24]
  S. Choudhary, M. Arora, H. Verma, M. Kumar, O. Silakari, Eur. J. Pharmacol. 899 (2021) 174027. doi: 10.1016/j.ejphar.2021.174027
25. [25]
  M. Sweeney, D. Conboy, S.I. Mirallai, F. Aldabbagh, Molecules 26 (2021) 2684. doi: 10.3390/molecules26092684
26. [26]
  Z. Xu, N.J. Singh, S.K. Kim, et al., Chem. Eur. J. 17 (2011) 1163–1170. doi: 10.1002/chem.201002105
27. [27]
  A. Kushwaha, S.K. Patil, D. Das, New J. Chem. 42 (2018) 9200–9208. doi: 10.1039/C8NJ01011K
28. [28]
  A.L. Brazeau, K. Yuan, S.B. Ko, I. Wyman, S. Wang, ACS Omega 2 (2017) 8625–8632. doi: 10.1021/acsomega.7b01631
29. [29]
  N. Kaur, G. Dhaka, J. Singh, New J. Chem. 39 (2015) 6125–6129. doi: 10.1039/C5NJ00683J
30. [30]
  M. Barwiolek, A. Wojtczak, A. Kozakiewicz, et al., New J. Chem. 42 (2018) 18559–18568. doi: 10.1039/C8NJ03801E
31. [31]
  P. Guo, A.A. Farahat, A. Paul, D.W. Boykin, W.D. Wilson, Chem. Sci. 12 (2021) 15849–15861. doi: 10.1039/D1SC04720E
32. [32]
  S.G. Wang, Y. Pang, M. Xue, Y. Yang, New J. Chem. 45 (2021) 19219–19223. doi: 10.1039/D1NJ04034K
33. [33]
  J.B. Birks, Rep. Prog. Phys. 38 (1975) 903–974. doi: 10.1088/0034-4885/38/8/001
34. [34]
  F.M. Winnik, Chem. Rev. 93 (1993) 587–614. doi: 10.1021/cr00018a001
35. [35]
  L. Lavaud, S. Pascal, K. Metwally, et al., Chem. Commun. 54 (2018) 12365–12368. doi: 10.1039/C8CC05851B
36. [36]
  Z. Chen, R. Haddoub, J. Mahe, et al., Chem. Eur. J. 22 (2016) 17820–17832. doi: 10.1002/chem.201602288
37. [37]
  A.A. Farahat, S. Iwamoto, M. Roche, D.W. Boykin, J. Heterocycl. Chem. 58 (2021) 2280–2286. doi: 10.1002/jhet.4353
38. [38]
  C.A. Hunter, J.K.M. Sanders, J. Am. Chem. Soc. 112 (1990) 5525–5534. doi: 10.1021/ja00170a016
39. [39]
  R. Thakuria, N.K. Nath, B.K. Saha, Cryst. Growth Des. 19 (2019) 523–528. doi: 10.1021/acs.cgd.8b01630
40. [40]
  M. Nishio, CrystEngComm 6 (2004) 130. doi: 10.1039/b313104a
41. [41]
  J. Polster, H. Lachmann, Spectrometric Titrations: Analysis of Chemical Equilibria, Wiley-VCH, 1989.
42. [42]
  P. Thordarson, Chem. Soc. Rev. 40 (2011) 1305–1323. doi: 10.1039/C0CS00062K
43. [43]
  E. Manandhar, P.J. Cragg, K.J. Wallace, Supramol. Chem. 26 (2014) 141–150. doi: 10.1080/10610278.2013.835050
1. [1]
  Xiuzheng Deng , Changhai Liu , Xiaotong Yan , Jingshan Fan , Qian Liang , Zhongyu Li . Carbon dots anchored NiAl-LDH@In₂O₃ hierarchical nanotubes for promoting selective CO₂ photoreduction into CH₄. Chinese Chemical Letters, 2024, 35(6): 108942-. doi: 10.1016/j.cclet.2023.108942
2. [2]
  Xueling Yu , Lixing Fu , Tong Wang , Zhixin Liu , Na Niu , Ligang Chen . Multivariate chemical analysis: From sensors to sensor arrays. Chinese Chemical Letters, 2024, 35(7): 109167-. doi: 10.1016/j.cclet.2023.109167
3. [3]
  Tian Cao , Xuyin Ding , Qiwen Peng , Min Zhang , Guoyue Shi . Intelligent laser-induced graphene sensor for multiplex probing catechol isomers. Chinese Chemical Letters, 2024, 35(7): 109238-. doi: 10.1016/j.cclet.2023.109238
4. [4]
  Neng Shi , Haonan Jia , Jixiang Zhang , Pengyu Lu , Chenglong Cai , Yixin Zhang , Liqiang Zhang , Nongyue He , Weiran Zhu , Yan Cai , Zhangqi Feng , Ting Wang . Accurate expression of neck motion signal by piezoelectric sensor data analysis. Chinese Chemical Letters, 2024, 35(9): 109302-. doi: 10.1016/j.cclet.2023.109302
5. [5]
  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
6. [6]
  Ying Chen , Li Li , Junyao Zhang , Tongrui Sun , Xuan Zhang , Shiqi Zhang , Jia Huang , Yidong Zou . Tailored ionically conductive graphene oxide-encased metal ions for ultrasensitive cadaverine sensor. Chinese Chemical Letters, 2024, 35(8): 109102-. doi: 10.1016/j.cclet.2023.109102
7. [7]
  Ting WANG , Peipei ZHANG , Shuqin LIU , Ruihong WANG , Jianjun ZHANG . A Bi-CP-based solid-state thin-film sensor: Preparation and luminescence sensing for bioamine vapors. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1615-1621. doi: 10.11862/CJIC.20240134
8. [8]
  Xiangshuai Li , Jian Zhao , Li Luo , Zhuohao Jiao , Ying Shi , Shengli Hou , Bin Zhao . Visual and portable detection of metronidazole realized by metal-organic framework flexible sensor and smartphone scanning. Chinese Chemical Letters, 2024, 35(10): 109407-. doi: 10.1016/j.cclet.2023.109407
9. [9]
  Yang Liu , Yan Liu , Kaiyin Yang , Zhiruo Zhang , Wenbo Zhang , Bingyou Yang , Hua Li , Lixia Chen . A selective HK2 degrader suppresses SW480 cancer cell growth by degrading HK2. Chinese Chemical Letters, 2024, 35(8): 109264-. doi: 10.1016/j.cclet.2023.109264
10. [10]
  Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089
11. [11]
  Tianbo Jia , Lili Wang , Zhouhao Zhu , Baikang Zhu , Yingtang Zhou , Guoxing Zhu , Mingshan Zhu , Hengcong Tao . Modulating the degree of O vacancy defects to achieve selective control of electrochemical CO₂ reduction products. Chinese Chemical Letters, 2024, 35(5): 108692-. doi: 10.1016/j.cclet.2023.108692
12. [12]
  Shuqi Yu , Yu Yang , Keisuke Kuroda , Jian Pu , Rui Guo , Li-An Hou . Selective removal of Cr(Ⅵ) using polyvinylpyrrolidone and polyacrylamide co-modified MoS₂ composites by adsorption combined with reduction. Chinese Chemical Letters, 2024, 35(6): 109130-. doi: 10.1016/j.cclet.2023.109130
13. [13]
  Yu Qin , Mingyang Huang , Chenlu Huang , Hannah L. Perry , Linhua Zhang , Dunwan Zhu . O₂-generating multifunctional polymeric micelles for highly efficient and selective photodynamic-photothermal therapy in melanoma. Chinese Chemical Letters, 2024, 35(7): 109171-. doi: 10.1016/j.cclet.2023.109171
14. [14]
  Shuangying Li , Qingxiang Zhou , Zhi Li , Menghua Liu , Yanhui Li . Sensitive measurement of silver ions in environmental water samples integrating magnetic ion-imprinted solid phase extraction and carbon dot fluorescent sensor. Chinese Chemical Letters, 2024, 35(5): 108693-. doi: 10.1016/j.cclet.2023.108693
15. [15]
  Yu-Hang Li , Shuai Gao , Lu Zhang , Hanchun Chen , Chong-Chen Wang , Haodong Ji . Insights on selective Pb adsorption via O 2p orbit in UiO-66 containing rich-zirconium vacancies. Chinese Chemical Letters, 2024, 35(8): 109894-. doi: 10.1016/j.cclet.2024.109894
16. [16]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
17. [17]
  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
18. [18]
  Zhen Shi , Wei Jin , Yuhang Sun , Xu Li , Liang Mao , Xiaoyan Cai , Zaizhu Lou . Interface charge separation in Cu2CoSnS4/ZnIn2S4 heterojunction for boosting photocatalytic hydrogen production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100201-100201. doi: 10.1016/j.cjsc.2023.100201
19. [19]
  Li Lin , Song-Lin Tian , Zhen-Yu Hu , Yu Zhang , Li-Min Chang , Jia-Jun Wang , Wan-Qiang Liu , Qing-Shuang Wang , Fang Wang . Molecular crowding electrolytes for stabilizing Zn metal anode in rechargeable aqueous batteries. Chinese Chemical Letters, 2024, 35(7): 109802-. doi: 10.1016/j.cclet.2024.109802
20. [20]
  Kezhen Qi , Shu-yuan Liu , Ruchun Li . Selective dissolution for stabilizing solid electrolyte interphase. Chinese Chemical Letters, 2024, 35(5): 109460-. doi: 10.1016/j.cclet.2023.109460

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(230)
HTML views(10)

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

Imidazobenzimidazole fused aza-calix[4]arenes: Synthesis, structure, and Zn2+-selective colorimetric-fluorometric sensor

Metrics

通讯作者: 陈斌, bchen63@163.com

Imidazobenzimidazole fused aza-calix[4]arenes: Synthesis, structure, and Zn²⁺-selective colorimetric-fluorometric sensor