Terephthaloyl Chloride Bridged Bis(β-cyclodextrin) and Their Synergetic Bonding Behaviors with Dyes

doi:10.6023/cjoc201411011

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (6): 1330-1334.DOI: 10.6023/cjoc201411011 Previous Articles Next Articles

Notes

对苯二甲酰氯桥联β-环糊精的合成及其对染料分子的协同键合

彭龙, 刘慧君, 胡趁, 孙允凯, 龙威

南华大学化学化工学院衡阳 421001

收稿日期:2014-11-07 修回日期:2015-01-25 发布日期:2015-02-28
通讯作者: 刘慧君 E-mail:liuhuijun@usc.edu.cn
基金资助:
国家自然科学基金(Nos. 11375084, 11305086 )资助项目.

Terephthaloyl Chloride Bridged Bis(β-cyclodextrin) and Their Synergetic Bonding Behaviors with Dyes

Peng Long, Liu Huijun, Hu Cheng, Sun Yunkai, Long Wei

College of Chemical Engineering, University of South China, Hengyang 421001

Received:2014-11-07 Revised:2015-01-25 Published:2015-02-28
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 11375084, 11305086).

1. Terephthaloyl Chloride Bridged Bis(β-cyclodextrin) and Their Synergetic Bonding Behaviors with Dyes.PDF(268KB)

Abstract

A novel bridged bis(β-cyclodextrin) with rigid aromatic diamino tethers were synthesized by the reaction of terephthaloyl chloride with β-cyclodextrin. The novel bridged bis(β-cyclodextrin) was analyzed by ¹H NMR, IR, UV and elemental analysis. The complex stability constants (K_S) for the inclusion complexation of these bis(β-cyclodextrin) with several dyes possessing different shapes and electron intensities were determined by means of fluorescence and UV-Vis titrations at 25 ℃ in phosphate buffer solution (pH=7.2). The results show that the bridged bis(β-cyclodextrin) showed much higher binding ability. Compared with native β-cyclodextrin, the binding abilities of the bridged bis(β-cyclodextrin) upon inclusion complexation to TNS, ANS, AR, NR and RhB were increased 3.3, 15.3, 2.2, 12.5, and 5.8 times, respectively. The cooperative binding ability of the bis(β-cyclodextrin) was discussed from the viewpoints of size/shape-fit interaction and multiple recognition mechanism.

Key words: bridged bis(β-cyclodextrin), synergetic bonding, dyes, molecular recognition, supramolecular chemistry

Cite this article

Peng Long, Liu Huijun, Hu Cheng, Sun Yunkai, Long Wei. Terephthaloyl Chloride Bridged Bis(β-cyclodextrin) and Their Synergetic Bonding Behaviors with Dyes[J]. Chin. J. Org. Chem., 2015, 35(6): 1330-1334.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Zhou, D.-X.; Sun, T.; Deng, W. Chin. J. Org. Chem. 2012, 32, 239 (in Chinese). (周冬香, 孙涛, 邓维, 有机化学, 2012, 32, 239.)
[2] Wan, J.-M.; Hu, Z.-W.; Chen, W.-X.; Zheng, S.-R.; Lü, S.-S.; Zhang, L. Acta Phys.-Chim. Sin. 2006, 22, 244 (in Chinese). (万军民, 胡智文, 陈文兴, 郑世睿, 吕慎水, 张利, 物理化学学报, 2006, 22, 244.)
[3] Abdel-Naby, M. A.; El-Refai, H. A.; Abdel-Fattah, A. F. J. Appl. Microbiol. 2011, 111, 1129.
[4] Thombre, R. S.; Kanekar, P. P. J. Microbiol. Biotechnol. Res. 2013, 3, 57.
[5] Chen, Y.; Han, N.; Yang, H.; Liu, Y. Acta Chim. Sinica 2007, 65, 1076 (in Chinese). (陈湧, 韩宁, 杨华, 刘育, 化学学报, 2007, 65, 1076.)
[6] Shen, H.-M.; Ji, H.-B.; Wu, H.-K.; Shi, H.-X. Chin. J. Org. Chem. 2014, 34, 1549 (in Chinese). (沈海民, 纪红兵, 武宏科, 史鸿鑫, 有机化学, 2014, 34, 1549.)
[7] Ueno, A.; Ikeda, A.; Ikeda, H. J. Org. Chem. 1999, 64, 387.
[8] Breslow, R.; Zhang, X.; Xu, R.; Maletic, M.; Merger, R. J. Am. Chem. Soc. 1996, 118, 11678.
[9] Fujita, K.; Ishizu, T.; Minamiura, N.; Yamamoto, T. Chem. Lett. 1991, 1889.
[10] Khan, A. R.; Forgo, P.; Stine, K. J.; D’Souza, V. T. Chem. Rev. 1998, 98, 1977.
[11] Zhang, H.-C.; Liu, Z.-N.; An, W.; Hao, A.-Y.; Sun, L.-Z. Chin. J. Org. Chem. 2010, 30, 1279 (in Chinese). (张华承, 刘召娜, 安伟, 郝爱友, 孙立臻, 有机化学, 2010, 30, 1279.)
[12] Zhang, Y.; Li, L.-S.; Cheng, B.-P. Chin. J. Anal. Chem. 2014, 42, 375 (in Chinese). (张杨, 李来生, 程彪平, 分析化学, 2014, 42, 375.)
[13] Ren, X. J.; Xue, Y.; Liu, J. Q.; Zhang, D.; Zheng, J.; Luo, G. M.; Guo, C. H.; Mu, Y.; Shen, J. C. ChemBioChem 2002, 3, 356.
[14] Martinez, A.; Mellet, C. O.; Fernandez, J. M. G. Chem. Soc. Rev. 2013, 42, 4746.
[15] Zhou, R.-D.; Li, L.-S.; Cheng, B.-P.; Nie, G.-Z.; Zhang, H.-F. Acta Chim. Sinica 2014, 72, 720 (in Chinese) . (周仁丹, 李来生, 程彪平, 聂桂珍, 张宏福, 化学学报, 2014, 72, 720.)
[16] Liu, Y.; You, C.-C.; Zhang, H.-Y. Supramolecular Chemistry——Molecular Recognition and Assembly of Synthetic Receptors, Nankai University Press, Tianjin, 2001, pp. 241～242 (in Chinese). (刘育, 尤长城, 张衡益, 超分子化学——合成受体的分子识别与组装, 天津, 南开大学出版社, 2001, pp. 241～242.)
[17] Benesi, H. A.; Hidebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703.
[18] Liu, Y.; You, C.-C.; Chen, Y.; Wada, T.; Inoue, Y. J. Org. Chem. 1999, 64, 7781～7787.
[19] Liu, Y.; Chen, Y.; Li, B.; Wada, T.; Inoue, Y. Chem. Eur. J. 2001, 7, 2528.
[20] Li, L; Li, X.-Y.; Liu, Y. Chin. Sci. Bull. 2003, 48, 2442 (in Chinese). (李莉, 李晓云, 刘育, 科学通报, 2003, 48, 2442.)
[21] Zhao, Y; Yang, Z.-M.; Zhu, H.-Y. Acta Phys.-Chim. Sin. 2007, 23, 394 (in Chinese). (赵焱, 杨自明, 朱洪友等, 物理化学学报, 2007, 23, 394.)
[22] Cabrer, P. R.; Alvarez-Parrilla, E.; Meijida, F.; Seijas, J. A.; Ntifiez, E. R.; Zato, J. V. Langmuir 1999, 15, 5489.

对苯二甲酰氯桥联β-环糊精的合成及其对染料分子的协同键合

Terephthaloyl Chloride Bridged Bis(β-cyclodextrin) and Their Synergetic Bonding Behaviors with Dyes

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Li Guan, Yanyan Zhou, Yongbao Mao, Kaisen Fu, Wenhui Guan, Yile Fu. Research Progress in the Synthesis of Polymethine Chain Modified Cyanine Dyes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2682-2698.
[2]	Fen Li, Chuanzhi Liu, Zhiyuan Hu, Panpan Luo, Rongzheng Cui, Yanke Huang, Xinming Liu, Lantao Liu, Wei Wu. Intermolecular Halogen and Hydrogen Bonding-Controlled Self-Assembly of Network Structures [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 705-711.
[3]	Huiming Lu, Lamaocao Ma, Hengchang Ma. Research Progress and Prospect of Aggregation-Induced Emission Supramolecular Luminescence Materials [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4075-4105.
[4]	Jianwen Qiu, Meng Liu, Xinyi Xiong, Yong Gao, Hu Zhu. Research Progress in High Brightness Near Infrared Fluorescent Dyes [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3745-3760.
[5]	Bin-Kai Liu, Kun-Xu Teng, Li-Ya Niu, Qing-Zheng Yang. Progress in the Synthesis of Boron Dipyrromethene (BODIPY) Fluorescent Dyes [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1265-1285.
[6]	Jingjing Guo, Minjie Guo. Progress in Design and Application of Supramolecular Fluorescent Systems Based on Difluoroboron-Dipyrromethene and Macrocyclic Compounds [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2946-2963.
[7]	Xiao Tangxin, Zhou Ling, Wei Xiaoyan, Li Zhengyi, Sun Xiaoqiang. Supramolecular Copolymers Driven by Quadruple Hydrogen Bonding and Host-Guest Interactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 944-949.
[8]	Huang Guobao, Chen Zhilin, Wei Xiansheng, Chen Yu, Li Xiuying, Zhong Hui, Tan Mingxiong. Recent Progress on the Construction and Function of Macrocyclic Compounds Containing Hydrogen Bond Donors [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 614-624.
[9]	Qi Lijie, Ding Yihan, Xiao Tangxin, Wu Haoran, Diao Kai, Bao Cheng, Shen Yong, Li Zhengyi, Sun Xiaoqiang, Wang Leyong. Supramolecular Self-Assembly of Dioxyphenylene Bridged Ureidopyrimidinone Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3847-3852.
[10]	Li Jing, Han Ying, Chen Chuanfeng. Recent Advances in Novel Macrocyclic Arenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3714-3737.
[11]	Wang Jiao, Yao Hong, Zhou Qi, Kan Xiaotong, Fan Yanqing, Guan Xiaowen, Zhang Youming, Lin Qi, Wei Taibao. Molecule-Responsive Supramolecular Hydrogel Constructed from Pillar[5]arene Based on Host-Guest System [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 175-180.
[12]	Zhou Jia, Liu Lu, Zhong Cheng, Fu Yang, Song Zhibin, Peng Yiyuan. Synthesis and Luminescent Properties of 6-Methoxy-quinazolinone-pyridine Difluoroboron Dyes [J]. Chin. J. Org. Chem., 2019, 39(5): 1444-1449.
[13]	Li, Sicong, Ji, Shaocong, Zhao, Liang, Liao, Xiaoyu, Liu, Chuanfeng, Tang, Haodong, Shu, Zhengning, Yang, Peng, Pei, Yuehu. Syntheses and Property Evaluation of N-Salicylaldehyde Hydrazone Modified 11-Azaartemisinins and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2860-2866.
[14]	Liu Chuan-Zhi, Wang Hui, Zhang Dan-Wei, Zhao Xin, Li Zhan-Ting. Study on Halogen Bonding of Organofluorine Compounds in China [J]. Chin. J. Org. Chem., 2019, 39(1): 28-37.
[15]	Xu Wenxiu, Dai Xiaoqiang, Xu Hanjing, Weng Jianquan. Application of Oxime Organic Dyes in Visible-Light-Induced Organic Synthesis [J]. Chin. J. Org. Chem., 2018, 38(11): 2807-2832.