Study on the Host-Guest Interactions Between Tetramethyl Cucurbit[6]uril and Benzimidazole Derivatives

doi:10.1007/s40242-023-3078-1

高等学校化学研究 ›› 2023, Vol. 39 ›› Issue (6): 1017-1022.doi: 10.1007/s40242-023-3078-1

Study on the Host-Guest Interactions Between Tetramethyl Cucurbit[6]uril and Benzimidazole Derivatives

YANG Naqin, DAI Xue, MA Yue, YANG Xinan, and MA Peihua

Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, College of Chemistry and Chemical Engineering, Guizhou University, Guiyang 550025, P.R. China

收稿日期:2023-03-24 出版日期:2023-12-01 发布日期:2023-11-18
通讯作者: MA Peihua E-mail:phma@gzu.edu.cn
基金资助:
This work was supported by the National Natural Science Foundation of China (No.22161010).

Study on the Host-Guest Interactions Between Tetramethyl Cucurbit[6]uril and Benzimidazole Derivatives

YANG Naqin, DAI Xue, MA Yue, YANG Xinan, and MA Peihua

Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, College of Chemistry and Chemical Engineering, Guizhou University, Guiyang 550025, P.R. China

Received:2023-03-24 Online:2023-12-01 Published:2023-11-18
Contact: MA Peihua E-mail:phma@gzu.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (No.22161010).

摘要/Abstract

摘要： In this paper, ¹H NMR spectroscopy, isothermal titration calorimetry, X-ray crystallography and other characterization methods were used to investigate the interaction modes of tetramethyl cucurbit[6]uril (TMeQ[6]) and three benzimidazole derivatives in an aqueous solution-solid state. The results showed that the aromatic ring moieties in the three derivatives all entered the cavity of TMeQ[6] and their substituents were located at the port of TMeQ[6], forming 1:1 host-guest inclusion complexes. The crystal structures showed that the aromatic part of the benzimidazole derivatives interacted with the cavity of TMeQ[6] via hydrogen bond interactions and the N atoms on the benzimidazole ring formed hydrogen bonds with the carbonyl oxygen of TMeQ[6]. The ion-dipole interactions between [ZnCl₄]^2- and TMeQ[6] formed supramolecular self-assembly entities.

关键词: Tetramethyl cucurbit[6]uril (TMeQ[6]), Benzimidazole derivative, Host-guest interaction, Crystal structure

Abstract: In this paper, ¹H NMR spectroscopy, isothermal titration calorimetry, X-ray crystallography and other characterization methods were used to investigate the interaction modes of tetramethyl cucurbit[6]uril (TMeQ[6]) and three benzimidazole derivatives in an aqueous solution-solid state. The results showed that the aromatic ring moieties in the three derivatives all entered the cavity of TMeQ[6] and their substituents were located at the port of TMeQ[6], forming 1:1 host-guest inclusion complexes. The crystal structures showed that the aromatic part of the benzimidazole derivatives interacted with the cavity of TMeQ[6] via hydrogen bond interactions and the N atoms on the benzimidazole ring formed hydrogen bonds with the carbonyl oxygen of TMeQ[6]. The ion-dipole interactions between [ZnCl₄]^2- and TMeQ[6] formed supramolecular self-assembly entities.

Key words: Tetramethyl cucurbit[6]uril (TMeQ[6]), Benzimidazole derivative, Host-guest interaction, Crystal structure

YANG Naqin, DAI Xue, MA Yue, YANG Xinan, and MA Peihua. Study on the Host-Guest Interactions Between Tetramethyl Cucurbit[6]uril and Benzimidazole Derivatives[J]. 高等学校化学研究, 2023, 39(6): 1017-1022.

YANG Naqin, DAI Xue, MA Yue, YANG Xinan, and MA Peihua. Study on the Host-Guest Interactions Between Tetramethyl Cucurbit[6]uril and Benzimidazole Derivatives[J]. Chemical Research in Chinese Universities, 2023, 39(6): 1017-1022.

参考文献

[1] Freeman W. A., Mock W. L., Shih N. Y., J. Am. Chem. Soc., 1981, 103, 7367
[2] Kim J., Jung I. S., Kim S. Y., Lee E., Kang J. K., Sakamoto S., Yamaguchi K., Kim K., J. Am. Chem. Soc., 2000, 122, 540
[3] Liu S. M., Zavalij P. Y., Isaacs L., J. Am. Chem. Soc., 2005, 127, 16798
[4] Li Q., Qiu S. C., Zhang J., Chen K., Huang Y., Xiao X., Zhang Y. J., Li F., Zhang Y. Q., Xue S. F., Zhu Q. J., Tao Z., Lindoy L. F., Wei G., Org. Lett., 2016, 18, 4020
[5] Cheng X. J., Liang L. L., Chen K., Ji N. N., Xiao X., Zhang J. X., Zhang Y. Q., Xue S. F., Zhu Q. J., Ni X. L., Tao Z., Angew. Chem. Int. Ed., 2013, 52, 7252
[6] Chen K., Hua Z. Y., Zhao J. L., Redshaw C., Tao Z., Inorg. Chem. Front., 2022, 9, 2753
[7] Yang D., Liu M., Xiao X., Tao Z., Redshaw C., Coordin. Chem. Rev., 2021, 434, 213733
[8] Chen K., Ge W. W., Xu J., Zhang S. M., Li Y. W., Hua Z. Y., Tao Z., J. Mol. Struct., 2019, 1181, 220
[9] Shen F. F., Zhao J. L., Chen K., Hua Z. Y., Chen M. D., Zhang Y. Q., Zhu Q. J., Tao Z., CrystEngComm, 2017, 19, 2464
[10] Ni X. L., Xue S. F., Tao Z., Zhu Q. J., Lindoy L. F., Wei G., Coordin. Chem. Rev., 2015, 287, 89
[11] Wu H., Wang Y., Jones L. O., Liu W. Q., Zhang L., Song B., Chen X. Y., Stern C. L., Schatz G. C., Stoddart J. F., Angew. Chem. Int. Ed., 2021, 60, 17587
[12] Wu H., Jones L. O., Wang Y., Shen D. K., Liu Z. C., Zhang L., Cai K., Jiao Y., Stern C. L., Schatz G. C., Stoddart J. F., ACS Appl. Mater. Interfaces, 2020, 12, 38768
[13] Shan P. H., Tu S. C., Lin R. L., Tao Z., Liu J. X., Xiao X., CrystEngComm, 2017, 19, 2168
[14] Wang C. Z., Zhao W. X., Shen F. F., Zhang Y. Q., Zhu Q. J., Xiao X., Tao Z., CrystEngComm, 2016, 18, 2112
[15] Qu Y. X., Zhou K. Z., Chen K., Zhang Y. Q., Xiao X., Zhou Q. D., Tao Z., Ma P. H., Wei G., Inorg. Chem., 2018, 57, 7412.
[16] Rad N., Sashuk V., Chem. Commun., 2022, 58, 5249
[17] Tang B. H., Zhao J. T., Xu J. F., Zhang X., Chem. Eur. J., 2020, 26, 15446
[18] Zhao Y. J., Xue S. F., Zhu Q. J., Tao Z., Zhang J. X., Wei Z. B., Long L. S., Hu M. L., Xiao H. P., Day A. I., Chin. Sci. Bull., 2004, 49, 1111
[19] Lin R. L., Fang G. S., Sun W. Q., Liu J. X., Scl. Rep., 2016, 6, 39057
[20] Meng Y., Zhao W. W., Zheng J., Jiang D. F., Gao J., Jin Y. M., Ma P. H., RSC Adv., 2021, 11, 3470
[21] Xiao X., Gao Z. Z., Shan C. L., Tao Z., Zhu Q. J., Xue S. F., Liu J. X., Phys. Chem. Chem. Phys., 2015, 17, 8618
[22] Cong H., Tao L. L., Yu Y. H., Tao Z., Yang F., Zhao Y. J., Xue S. F., Lawrance G. A., Wei G., J. Phys. Chem. A, 2007, 111, 2715
[23] Yang B., Xiao X., Zhang Y. Q., Zhu Q. J., Xue S. F., Tao Z., Wei G., RSC Adv., 2014, 4, 44359
[24] Yang L. G., Kan J. L., Wang X., Zhang Y. H., Tao Z., Liu Q. Y., Wang F., Xiao X., Front. Chem., 2018, 6, 289
[25] Huang Y. H., Geng Q. X., Jin X. Y., Cong H., Qiu F., Xu L., Tao Z., Wei G., Sensor. Actuat. B: Chem., 2017, 243, 1102
[26] Akhtar W., Khan M. F., Verma G., Shaquiquzzaman M., Rizvi M. A., Mehdi S. H., Akhter M., Alam M. M., Eur. J. Med. Chem., 2017, 126, 705
[27] Bistrović A., Krstulović L., Stolić I., Drenjančević D., Talapko J., Taylor M. C., Kelly J. M., Bajić M., Raić-Malić S., J. Enzym. Inhib. Med. Chem., 2018, 33, 1323
[28] Arora R. K., Kaur N., Bansal Y., Bansal G., Acta Pharm. Sin. B, 2014, 4, 368
[29] de Oliveira H. C., Rodrigues M. L., Fungal. Biol. Rev., 2021, 37, 27
[30] Tonelli M., Novelli F., Tasso B., Vazzana I., Sparatore A., Boido V., Sparatore F., la Colla P., Sanna G., Giliberti G., Busonera B., Farci P., Ibba C., Loddo R., Bioorgan. Med. Chem., 2014, 22, 4893
[31] Wu L. T., Jiang Z., Shen J. J., Yi H., Zhan Y. C., Sha M. Q., Wang Z., Xue S. T., Li Z. R., Eur. J. Med. Chem., 2016, 114, 328
[32] Ge J. Y., Xue S. F., Zhu Q. J., Tao Z., Zhang J. X., J. Incl. Phenom. Macro., 2007, 58, 63
[33] Zhao Y. J., Pourgholami M. H., Morris D. L., Collins J. G., Day A. I., Org. Biomol. Chem., 2010, 8, 3328
[34] Albdallah S. K., Assaf K. I., Bodoor K., Al-Sakhen N. A., Malhis L. D., Alhmaideen A. I., El-Barghouthi M. I., J. Solution. Chem., 2018, 47, 1768
[35] Wang Q., Guo J. Z., Luo D., Ye M. F., Lin R. L., Sun W. Q., Liu J. X., Phys. Chem. Chem. Phys., 2022, 24, 25930
[36] Zheng L. M., Zhang K., Lin R. L., Chu X. F., Liu J. X., J. Incl. Phenom. Macro., 2020, 96, 125
[37] Lu Y., Yu Z. C., Yang X. N., Dai J. J., Shan P. H., Feng X. H., Tao Z., Redshaw C., Xiao X., Chin. Chem. Lett., 2022, 108040
[38] Qu Y. X., Lin R. L., Zhang Y. Q., Zhou K. Z., Zhou Q. D., Zhu Q. J., Tao Z., Ma P. H., Liu J. X., Wei G., Org. Chem. Front., 2017, 4, 1799
[39] Shi Z. L., Liu X. K., Zhou Y. H., Cong H., Polym. Adv. Technol., 2022, 33, 2498
[40] Zheng J., Ma Y., Yang X. N., Ma P. H., RSC Adv., 2022, 12, 18736

Study on the Host-Guest Interactions Between Tetramethyl Cucurbit[6]uril and Benzimidazole Derivatives

Study on the Host-Guest Interactions Between Tetramethyl Cucurbit[6]uril and Benzimidazole Derivatives

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	PANG Kuan, XUE Huan, LIU Haixiong, SUN Jing, LIU Tianfu. Chelating Metal Ions in a Metal-Organic Framework for Constructing a Biomimetic Catalyst Through Post-modification[J]. 高等学校化学研究, 2022, 38(6): 1542-1546.
[2]	YANG Miao, WANG Wenjing, SU Kongzhao, YUAN Daqiang. Dimeric Calix[4]resorcinarene-based Porous Organic Cages for CO₂/CH₄ Separation[J]. 高等学校化学研究, 2022, 38(2): 428-432.
[3]	HUA Chen, YI Pin, LIU Wencong, WANG Mengfan, NIU Zheng, LANG Jianping. Coordination Polymers with Bipyridyl Diene and Triene Ligands: Synthesis, Structures and Luminescent Properties[J]. 高等学校化学研究, 2022, 38(1): 209-216.
[4]	ZHANG Wenqi, LIN Zhengguo, CHI Yingnan, HONG Jie, YAN Li, HU Changwen. Assembly of Three Scandium-containing Heteropolytungstates Based on a Building-block Synthetic Strategy[J]. 高等学校化学研究, 2020, 36(6): 1161-1167.
[5]	ZANG Jiahe, ZHANG Qing'an, SUN Dalin. Crystal Structures and Electrochemical Properties of R_1.5Ca_1.5MgNi₁₄(R=Nd, Gd and Er) Hydrogen Storage Alloys[J]. 高等学校化学研究, 2019, 35(6): 1040-1045.
[6]	WANG Dongmei, LOU Shengjun, YING Yiting, GUO Zhiqi, WANG Lijun. Assembly of Two Isostructural Metal-organic Frameworks Based on Hetero-N,O Donor Ligand for Detecting Nitro Explosives[J]. 高等学校化学研究, 2019, 35(5): 762-766.
[7]	MA Xiao, WANG Xiaohong, SHANG Fan, DING Zimei, HANG Xiaojing, HUANG Jie. Studies on 3-Amino-4-(1H-tetrazol-5-yl)-furazan: Crystal Structure, Thermal Behavior and Energetic Performance[J]. 高等学校化学研究, 2019, 35(5): 848-853.
[8]	ZHONG Liangxuan, LIU Mingyue, ZHANG Bowei, SUN Yaqiu, XU Yanyan. Syntheses, Crystal Structures, Magnetic and Near-infrared Luminescence Properties of 3d-4f Coordination Polymers Cu₂Pr₂, Cu₂Eu₂ and Cu₄Tb₂[J]. 高等学校化学研究, 2019, 35(4): 693-699.
[9]	LIU Qianqian, GUO Yuan, WU Tun, CHEN Mingzhao, XIE Tingzheng, WANG Pingshan. Novel Terpyridine-bridged Parallel Dication Metallo-bisviologens and Their Supramolecular Complexes[J]. 高等学校化学研究, 2019, 35(2): 229-234.
[10]	YU Yanzhao, CAO Jiapeng, XU Yan. Two Pentavanadate-based Organic-inorganic Materials with Third-order NLO Properties[J]. 高等学校化学研究, 2019, 35(1): 1-4.
[11]	DING Zimei, CAO Wenli, ZHENG Hui, HUANG Jie, XU Kangzhen, SONG Jirong. Synthesis, Structure Characteristic and Thermal Behavior of Two New Metal-organic Azo-triazole Compounds: [Zn(phen)₃]·ZTO·6H₂O and[Cu(phen)₃]·ZTO·6H₂O[J]. 高等学校化学研究, 2018, 34(6): 1009-1013.
[12]	CHEN Xiang, ZENG Tian, ZHANG Cong, GUO Zhaoqi, LI Shuailei, MAI Tao, GAO Rong, MA Haixia. Crystal Structures, Thermal Behavior Analysis and Thermal Safety of Two Energetic Salts of Hydrazinyl-1,2,4,5-tetrazine with 3,5-Dinitrosalicylic Acid[J]. 高等学校化学研究, 2018, 34(6): 959-964.
[13]	LIU Chao, LIU Yijie, ZHANG Lili, JIANG Kun, ZHANG Li. Two Coordination Compounds Bearing Bis(2-dimethylaminoethyl) Ether: Syntheses, Crystal Structures and Catalytic Application to the Henry Reaction[J]. 高等学校化学研究, 2018, 34(3): 358-362.
[14]	WANG Jingyang, ZHANG Meng, XU Xiaodong, FENG Jing, WANG Yanli, ZHANG Milin, HAN Wei, CHEN Yitung, TIAN Guoxin. Synthesis and Characterization of [Cu(N-MeIm)₄(BF₄)₂] in Ionic Liquid[J]. 高等学校化学研究, 2018, 34(1): 8-12.
[15]	ZHOU Jinhua, LI Jingjing, LI Jie, REN Guoyu, REN Yinghui, MA Haixia. Structure and Enhanced Antifungal Activity of a Divalent Cobalt(II) Complex with Hexaconazole[J]. 高等学校化学研究, 2017, 33(6): 864-868.