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Chinese Journal of Organic Chemistry >

2017 , Vol. 37 >Issue 3: 603 - 607

DOI: https://doi.org/10.6023/cjoc201612033

ARTICLE

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

  • Yao Huan ,
  • Sun Jiaonan ,
  • Ke Hua ,
  • Yang Liupan ,
  • Li Jiarong ,
  • Jiang Wei
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  • 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 date: 2016-12-08

  Revised date: 2016-12-27

  Online published: 2017-01-04

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21302090, 21572097) and the Thousand Talents Program-Youth.

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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

Cite this article

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

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