Impact of 2,6-connectivity in azulene

Optical properties and stimuli responsive behavior

Michael Koch, Olivier Blacque, Koushik Venkatesan*

*Corresponding author for this work

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The possible incorporation of the redox active, small donor acceptor molecule azulene as a core structure for potential optoelectronic applications has been evaluated. The synthesis and characterization of different isomers of di(phenylethynyl)azulene 1-4 have been successfully carried out. The photophysical properties as well as their stimuli responsive behavior reflecting their corresponding electronic properties were also investigated. The experimental observations show that 2,6-connection (3) exhibits intense luminescence and shows the strongest stimuli responsive behavior upon acid treatment. DFT calculations of 3 reveal the highest contributions of the alkyne substituents at the 2- and 6-position of the azulene to the ground- and excited state that makes the 2,6-connectivity at azulene a very promising candidate for low band-gap conjugated materials.

Original languageEnglish
Pages (from-to)7400-7408
Number of pages9
JournalJournal of Materials Chemistry C
Volume1
Issue number44
DOIs
Publication statusPublished - 28 Nov 2013
Externally publishedYes

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