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Synthesis, Structure and Properties of Benzo[1,2‐ f :5,4‐ f′ ]‐diquinoline Derivatives: A Remarkably Strong Intramolecular CH···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.