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

ARTICLE

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   

  1. 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 出版日期:2017-03-25 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 Huana,b, Sun Jiaonanb, Ke Huab, Yang Liupanb, Li Jiaronga, Jiang Weib   

  1. 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 Online:2017-03-25 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.

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