Synthesis, Structure and Properties of Benzo[1,2‐ f :5,4‐ f′ ]‐diquinoline Derivatives: A Remarkably Strong Intramolecular CH···O Hydrogen Bond | Zendy

Zhang Chun | Zendy; Peng Xiaoxia | Zendy; Chen Chuanfeng | Zendy

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Synthesis, Structure and Properties of Benzo[1,2‐ f :5,4‐ f′ ]‐diquinoline Derivatives: A Remarkably Strong Intramolecular CH···O Hydrogen Bond

Author(s) -

Zhang Chun,

Peng Xiaoxia,

Chen Chuanfeng

Publication year - 2011

Publication title -

chinese journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.28

H-Index - 41

eISSN - 1614-7065

pISSN - 1001-604X

DOI - 10.1002/cjoc.201100314

Subject(s) - chemistry , intramolecular force , trifluoroacetic acid , hydrogen bond , molecule , proton nmr , proton , chemical shift , fluorescence , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , physics , quantum mechanics

A series of benzo[1,2‐ f :5,4‐ f′ ]diquinoline derivatives were synthesized starting from 2,7‐diaminoanthracene, and their structures were determined by NMR, MS spectra and X‐ray analysis. They showed a remarkably strong intramolecular CH···O hydrogen bond, which resulted in an unexpected downfield chemical shift of the aromatic proton in CDCl 3 . Moreover, a significant fluorescent change of molecule 1b in the presence of trifluoroacetic acid (TFA) was also observed.

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