Issue 90, 2014

Solvatochromic studies of pull–push molecules containing dimethylaniline and aromatic hydrocarbon linked by an acetylene unit

Abstract

Pull–push molecules containing dimethylaniline and aromatic hydrocarbon linked by an acetylene unit were studied using spectroscopic methods and DFT theoretical calculations. Spectral and photophysical properties of N,N-dimethyl-4-(naphthalen-1-ylethynyl)aniline, N,N-dimethyl-4-(naphthalen-2-ylethynyl)aniline, 4-(athracen-9-ylethynyl)-N,N-dimethylaniline were studied in 26 solvents (non-polar, polar aprotic and protic). The influence of solvent properties on the spectral and photophysical properties of the compounds studied was analyzed using empirical Riechardt's solvent polarity index as well as Catalán and Kamlet–Tatf multi-parameter solvent scales. The change of the dipole moment in the excited state was estimated based on Bilot–Kawski theory. Using the solvatochromic method, the change of hydrogen bond energy in the excited state was calculated. Theoretical calculations confirm the conclusions arising from experimental studies.

Graphical abstract: Solvatochromic studies of pull–push molecules containing dimethylaniline and aromatic hydrocarbon linked by an acetylene unit

Supplementary files

Article information

Article type
Paper
Submitted
11 Jul 2014
Accepted
17 Sep 2014
First published
03 Oct 2014

RSC Adv., 2014,4, 48783-48795

Author version available

Solvatochromic studies of pull–push molecules containing dimethylaniline and aromatic hydrocarbon linked by an acetylene unit

I. Bylińska, M. Wierzbicka, C. Czaplewski and W. Wiczk, RSC Adv., 2014, 4, 48783 DOI: 10.1039/C4RA06999D

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