Citation: Yi-Feng WANG, Mou-Hai SHU. Synthesis and Crystal Structure of a Copper(II) Complex with Funnel-like Ligand Based on Calix[6]arene[J]. Chinese Journal of Structural Chemistry, ;2022, 41(3): 220318. doi: 10.14102/j.cnki.0254-5861.2011-3312 shu

Synthesis and Crystal Structure of a Copper(II) Complex with Funnel-like Ligand Based on Calix[6]arene

Yi-Feng WANG ,
Mou-Hai SHU ^,

School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, China

Corresponding author: Mou-Hai SHU, mhshu@sjtu.edu.cn
Received Date: 20 July 2021
Accepted Date: 8 November 2021

Fund Project: the Natural Science Foundation of Shanghai 19ZR1424900

Figures(5)

The preparation method of a funnel like ligand derived from calix[6]arene and tris(2-pyridyl-methyl)anime has been improved. The Cu(II) complex was obtained and characterized by ESI-MS, EPR, UV-Vis spectra and crystallographic analysis. In the complex, a guest acetonitrile molecule is introduced into the cavity of the ligand host via the coordination with Cu(II) center.
- Cu(II) complex,
- crystal structure,
- calix[6]arene,
- host-guest interaction
1. [1]
  Hong, C. M.; Bergman, R. G.; Raymond, K. N.; Toste, F. D. Self-assembled tetrahedral hosts as supramolecular catalysts. Acc. Chem. Res. 2018, 51, 2447−2455. doi: 10.1021/acs.accounts.8b00328
2. [2]
  Zarra, S.; Wood, D. M.; Roberts, D. A.; Nitschke, J. R. Molecular containers in complex chemical systems. Chem. Soc. Rev. 2015, 44, 419−432. doi: 10.1039/C4CS00165F
3. [3]
  Li, X.; Wu, J.; He, C.; Meng, Q.; Duan, C. Asymmetric catalysis within the chiral confined space of metal-organic architectures. Small 2019, 15, 1804770. doi: 10.1002/smll.201804770
4. [4]
  Brown, C. J.; Toste, D.; Bergman, R. G.; Raymond, K. N. Supramolecular catalysis in metal-ligand cluster hosts. Chem. Rev. 2015, 115, 3012−3035. doi: 10.1021/cr4001226
5. [5]
  Tan, C.; Chu, D.; Tang, X.; Liu, Y.; Xuan, W.; Cui, Y. Supramolecular coordination cages for asymmetric catalysis. Chem. Eur. J. 2019, 25, 662−672. doi: 10.1002/chem.201802817
6. [6]
  Percástegui, E. G.; Ronson, T. K.; Nitschke, J. R. Design and applications of water-soluble coordination cages. Chem. Rev. 2020, 120, 13480−13544. doi: 10.1021/acs.chemrev.0c00672
7. [7]
  Hasell, T.; Cooper, A. I. Porous organic cages: soluble, modular and molecular pores. Nat. Rev. Mater. 2016. 16053.
8. [8]
  Mastalerz, M. Porous shape-persistent organic cage compounds of different size, geometry, and function. Acc. Chem. Res. 2018, 51, 2411−2422. doi: 10.1021/acs.accounts.8b00298
9. [9]
  Liu, W.; Bobbala, S.; Stern, C. L.; Hornick, J. E.; Liu, Y.; Enciso, A. E.; Scott, E. A.; Stoddart, J. F. XCage: a tricyclic octacationic receptor forperylene diimide with picomolar affinity in water. J. Am. Chem. Soc. 2020, 142, 3165−3173. doi: 10.1021/jacs.9b12982
10. [10]
  Li, H.; Zhang, H.; Lammer, A. D.; Wang, M.; Li, X.; Lynch, V. M.; Sessler, J. L. Quantitative self-assembly of a purely organic three-dimensional catenane in water. Nat. Chem. 2015, 7, 1003−1008. doi: 10.1038/nchem.2392
11. [11]
  Hasell, T.; Wu, X.; Jones, J. T. A.; Bacsa, J.; Steiner, A.; Mitra, T.; Trewin, A.; Adams, D. J.; Cooper, A. I. Triply interlocked covalent organic cages. Nat. Chem. 2010, 2, 750−755. doi: 10.1038/nchem.739
12. [12]
  Zhang, Z. Q.; Ren, Q. X.; Tian, W. F.; Sun, W. H.; Cao, X. P.; Shi, Z. F.; Chow, H. F.; Kuck, D. Synthesis of enantiopure hydrocarbon cages based on an optically resolved C₃-symmetric triaminotribenzotriquinacene. Org. Lett. 2021, 23, 1478−1483. doi: 10.1021/acs.orglett.1c00176
13. [13]
  Liu, Z.; Nalluri, S. K. M.; Stoddart, J. F. Surveying macrocyclic chemistry: from flexible crown ethers to rigid cyclophanes. Chem. Soc. Rev. 2017, 46, 2459−2478. doi: 10.1039/C7CS00185A
14. [14]
  Ogoshi, T.; Yamagishi, T. A.; Nakamoto, Y. Pillar-shaped macrocyclic hosts pillar[n]arenes: new key players for supramolecular chemistry. Chem. Rev. 2016, 116, 7937−8002. doi: 10.1021/acs.chemrev.5b00765
15. [15]
  He, Q.; Vargas-Zúñiga, G. I.; Kim, S. H.; Kim, S. K.; Sessler, J. L. Macrocycles as ion pair receptors. Chem. Rev. 2019, 119, 9753−9835. doi: 10.1021/acs.chemrev.8b00734
16. [16]
  Jana, A.; Bähring, S.; Ishida, M.; Goeb, S.; Canevet, D.; Sallé, M.; Jeppesen, J. O.; Sessler, J. L. Functionalised tetrathiafulvalene-(TTF-) macrocycles: recent trends in applied supramolecular chemistry. Chem. Soc. Rev. 2018, 47, 5614−5645. doi: 10.1039/C8CS00035B
17. [17]
  He, C.; Sheng, T. P.; Dai, F. R.; Chen, Z. N. Sulfonylcalix[4]arene-based coordination supercontainers. Chin. J. Struct. Chem. 2020, 39, 2077−2084.
18. [18]
  Sheng, T. P.; Dai, F. R.; Zheng, G. Z.; Chen, Z. N. Synthesis, crystal structure and gas adsorption properties of metal-organic supercontainer based 2, 6-naphthalenedicarboxylate linker. Chin. J. Struct. Chem. 2021, 40, 311−316.
19. [19]
  Zeng, X.; Coquière, D.; Alenda, A.; Garrier, E.; Prangé, T.; Li, Y.; Reinaud, O.; Jabin, I. Efficient synthesis of calix[6]tmpa: a new calix[6]-azacryptand with unique conformational and host-guest properties. Chem. Eur. J. 2006, 12, 6393−6402. doi: 10.1002/chem.200600278
20. [20]
  Izzet, G.; Zeng, X.; Akdas, H.; Marrot, J.; Reinaud, O. Drastic effects of the second coordination sphere on neutral vs. anionic guest binding to a biomimetic Cu(II) center embedded in a calix[6]aza-cryptand. Chem. Commun. 2007, 8, 810−812.
21. [21]
  Thiabaud, G.; Guillemot, G.; Schmitz-Afonso, I.; Colasson, B.; Reinaud, O. Solid-state chemistry at an isolated copper(I) center with O₂. Angew. Chem. Int. Ed. 2009, 48, 7383−7386. doi: 10.1002/anie.200902691
22. [22]
  Tu, C. L.; Zheng, C.; Chen, Y.; Shu, M. H. Synthesis and reversible recognition for organic ammoniums of a molecular receptor based on calix[6]-arene. Chem. J. Chin. Univ. 2007, 28, 1917−1919.
23. [23]
  Ai, T. T.; Li, Q. Q.; Liang, T.; Tu, C. L; Shu, M. H. Syntheses and electrospray mass spectroscopy of functionalized N₄-calix[6]arene and complexes with copper(I, II) and zinc salts. Chin. J. Inorg. Chem. 2008, 24, 1159−1163.
24. [24]
  Gutsche, C. D.; Dhawan, B.; Leonis, M.; Stewart, D. p-tert-Butylcalix[6]arene. Org. Synth. 1990, 68, 238−238. doi: 10.15227/orgsyn.068.0238
25. [25]
  Janssen, R. G.; Vervoom, W.; Reinhoudt, D.; Casnati, A.; Freriks, M.; Pochini, A.; Ugozzoli, F.; Ungaro, R.; Nieto, P. M.; Carramolino, M. Procedure for the selective alkylation of calix[6]arenas at the lower rim. Synthesis 1994, 380−385.
26. [26]
  Newcomb, M.; Timko, J. M.; Walba, D. M.; Cram, D. J. Host-guest complexation. 3. Organization of pyridyl binding sites. J. Am. Chem. Soc. 1977, 99, 6392−6398. doi: 10.1021/ja00461a035
27. [27]
  Almaliti, J.; Al-Hamashi, A. A.; Negmeldin, A. T.; Hanigan, C. L.; Perera, L.; Pflum, M. K. H.; Casero, R. A.; Tillekeratne, L. M. V. Largazole analogues embodying radical changes in the depsipeptide ring: development of a more selective and highly potent analogue. J. Med. Chem. 2016, 59, 10642−10660. doi: 10.1021/acs.jmedchem.6b01271
28. [28]
  He, Z.; Chaimungkalanont, P. J.; Craig, D. C.; Colbran, S. B. Copper(II) complexes of 6-hydroxymethyl-substituted tris(2-pyridylmethyl)amine ligands. J. Chem. Soc. Dalton Trans. 2000, 9, 1419−1429.
29. [29]
  Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. C 2015, 71, 3−8. doi: 10.1107/S2053229614024218
30. [30]
  Sheldrick, G. M. SHELXT-integrated space-group and crystal structure determination. Acta Crystallogr. A 2015, 71, 3−8. doi: 10.1107/S2053273314026370
31. [31]
  Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C. Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1, 7-bis(N-methylbenzimidazol-2′-yl)-2, 6-dithiaheptane] copper(II) perchlorate. J. Chem. Soc. Dalton Trans. 1984, 1349−1356.
32. [32]
  Shu, M. H.; Sun, W. Y.; Duan, C. Y.; Fu, Y. J.; Zhang, W. J.; Tang, W. X. The influence of the linkage mode between bipyridine units in oligobipyridine ligands on the formation of copper-(I) and-(II) helicates. J. Chem. Soc. Dalton Trans. 1999, 729−734.
1. [1]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
2. [2]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
3. [3]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
4. [4]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
5. [5]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
6. [6]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
7. [7]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
8. [8]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
9. [9]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
10. [10]
  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
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.2023.100335
12. [12]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
13. [13]
  Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542
14. [14]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
15. [15]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
16. [16]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
17. [17]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
18. [18]
  Chao Ma , Cong Lin , Jian Li . MicroED as a powerful technique for the structure determination of complex porous materials. Chinese Journal of Structural Chemistry, 2024, 43(3): 100209-100209. doi: 10.1016/j.cjsc.2023.100209
19. [19]
  Zhijia Zhang , Shihao Sun , Yuefang Chen , Yanhao Wei , Mengmeng Zhang , Chunsheng Li , Yan Sun , Shaofei Zhang , Yong Jiang . Epitaxial growth of Cu_2-xSe on Cu (220) crystal plane as high property anode for sodium storage. Chinese Chemical Letters, 2024, 35(7): 108922-. doi: 10.1016/j.cclet.2023.108922
20. [20]
  Zhengzheng LIU , Pengyun ZHANG , Chengri WANG , Shengli HUANG , Guoyu YANG . Synthesis, structure, and electrochemical properties of a sandwich-type {Co₆}-cluster-added germanotungstate. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1173-1179. doi: 10.11862/CJIC.20240039

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(411)
HTML views(64)

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