Issue 5, 2012
From the journal:

New Journal of Chemistry

Synthesis and unexpected halochromism of carbazole-functionalized dithienophospholes

Monika Stolara  and  Thomas Baumgartner*a  

* Corresponding authors

a Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Canada
E-mail: Thomas.baumgartner@ucalgary.ca
Fax: +1 (403) 289-9488

Abstract

A series of π-conjugated donor–acceptor (D/A) chromophores using dithieno[3,2-b:2′,3′-d]phosphole oxide as an acceptor and 3,6-carbazole as a donor component have been synthesized and characterized. The studies involved several molecular species with D–A, A–D–A, D–A–D architecture, as well as a polymeric species (D–A)n. The different photophysical properties of the systems can be attributed to the carbazole unit de facto acting as aniline species for the π-conjugated system. Treatment of the donor–acceptor materials with acids resulted in the significant red shift of the absorption and emission wavelengths and the process was found to be reversible. Investigations via Density-Functional Theory (DFT) calculations revealed the nature of the unexpected red shift upon protonation.

Graphical abstract: Synthesis and unexpected halochromism of carbazole-functionalized dithienophospholes

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Article information

DOI
https://doi.org/10.1039/C2NJ40022G
Article type
Paper
Submitted
10 Jan 2012
Accepted
14 Feb 2012
First published
29 Feb 2012

New J. Chem., 2012,36, 1153-1160

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Synthesis and unexpected halochromism of carbazole-functionalized dithienophospholes

M. Stolar and T. Baumgartner, New J. Chem., 2012, 36, 1153 DOI: 10.1039/C2NJ40022G

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