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Noncovalent interactions in the design of bis-azo dyes

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Abstract

A series of new (1E,1′E)-2,2′-((perfluoro-1,4-phenylene)bis(2,2-dichloroethene-1,1-diyl))bis(1-(para-substituted phenyl)diazenes) have been synthesized via CuCl catalyzed olefination of the corresponding Schiff bases with CCl4 in the presence of tetramethylethylenediamine (TMEDA) in DMSO. Cl⋯O and Cl⋯F types of halogen bonds were found in these bis-azo dyes, which depend on the electron-donating or -accepting properties of the para-substituent (–OCH3, –CH3, –H, –F) of the azoaromatic ring. DFT calculations demonstrate that noncovalent interactions play a significant role in the stabilization of the intermolecular networks of the structures under study.

Graphical abstract: Noncovalent interactions in the design of bis-azo dyes

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Publication details

The article was received on 19 Jun 2019, accepted on 25 Jul 2019 and first published on 25 Jul 2019


Article type: Communication
DOI: 10.1039/C9CE00956F
CrystEngComm, 2019, Advance Article

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    Noncovalent interactions in the design of bis-azo dyes

    N. Q. Shikhaliyev, M. L. Kuznetsov, A. M. Maharramov, A. V. Gurbanov, N. E. Ahmadova, V. G. Nenajdenko, K. T. Mahmudov and A. J. L. Pombeiro, CrystEngComm, 2019, Advance Article , DOI: 10.1039/C9CE00956F

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