Citation: 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]. Chinese Journal of Organic Chemistry, ;2017, 37(3): 603-607. doi: 10.6023/cjoc201612033 shu

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

Corresponding author: Li Jiarong, jrli@bit.edu.cn Jiang Wei, jiangw@sustc.edu.cn
Received Date: 8 December 2016
Revised Date: 27 December 2016

Fund Project: Project supported by the National Natural Science Foundation of China 21572097Project supported by the National Natural Science Foundation of China 21302090

Figures(5)

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.
- host-guest chemistry,
- macrocyclic chemistry,
- bis-naphthalene
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