Synthesis of Bis-naphthalene and Their Derivatives and Their Complexation with Organic Cation

doi:10.6023/cjoc201612033

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 603-607.DOI: 10.6023/cjoc201612033 Previous Articles Next Articles

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桥联双萘及其衍生物的合成以及对有机阳离子的络合作用

姚欢^a,b, 孙娇囡^b, 柯华^b, 杨留攀^b, 李加荣^a, 蒋伟^b

a 北京理工大学化学与化工学院北京 100081;
b 南方科技大学化学系深圳 518055

收稿日期:2016-12-08 修回日期:2016-12-27 发布日期:2017-01-04
通讯作者: 李加荣,E-mail:jrli@bit.edu.cn;蒋伟,E-mail:jiangw@sustc.edu.cn E-mail:jrli@bit.edu.cn;jiangw@sustc.edu.cn
基金资助:
国家自然科学基金（Nos.21302090，21572097）和中组部“青年千人计划”资助项目.

Synthesis of Bis-naphthalene and Their Derivatives and Their Complexation with Organic Cation

Yao Huan^a,b, Sun Jiaonan^b, Ke Hua^b, Yang Liupan^b, Li Jiarong^a, Jiang Wei^b

a School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081;
b Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055

Received:2016-12-08 Revised:2016-12-27 Published:2017-01-04
Contact: 10.6023/cjoc201612033 E-mail:jrli@bit.edu.cn;jiangw@sustc.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21302090, 21572097) and the Thousand Talents Program-Youth.

1. Synthesis of Bis-naphthalene and Their Derivatives and Their Complexation with Organic Cation.PDF(257KB)

Abstract

In this research, the structure of the bis-naphthalene molecular resulting from 2-naphthol and 1,1,1',1'-tetramethoxypropane was modified, and six derivatives with different substituents, sidewalls or bridges were synthesized. Their structures were studied by X-ray crystallography and molecular modelling, and all possess curved architectures. Electrostatic potential energy surfaces show that their inner cavities are electron-rich, and may complex with organic cations through cation-π interactions. Their binding stoichiometry and association constants with the 1,4-diazabicyclo[2.2.2]octane (DABCO)-based organic cation were studied by ¹H NMR titration and Job's plot. The results show that electron-rich molecules have much stronger association, and reducing the carbon atom in the bridge significantly decreases their association ability. These novel curved structures may work as building blocks for the construction of new macrocyclic receptors.

Key words: host-guest chemistry, macrocyclic chemistry, bis-naphthalene

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Yao Huan, Sun Jiaonan, Ke Hua, Yang Liupan, Li Jiarong, Jiang Wei. Synthesis of Bis-naphthalene and Their Derivatives and Their Complexation with Organic Cation[J]. Chin. J. Org. Chem., 2017, 37(3): 603-607.

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桥联双萘及其衍生物的合成以及对有机阳离子的络合作用

Synthesis of Bis-naphthalene and Their Derivatives and Their Complexation with Organic Cation

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