Conjugated oligomers incorporating azulene building blocks-seven- vs. Five-membered ring connectivity

Elizabeth Amir, Masahito Murai, Roey J. Amir, John S. Cowart, Michael L. Chabinyc, Craig J. Hawker

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

The properties of isomeric azulene derivatives based on 7- versus 5-membered ring substitution were examined by the synthesis and characterization of well-defined electroactive oligomers. The substitution pattern was shown to dramatically influence solid-state, electronic and optical properties of the oligomers with acid-responsive materials only being observed when the azulenium cation could be directly stabilized by substituents in the 7-membered ring. Protonation was accompanied by a reversible color change and a strong red-shift of the absorption maximum as indicated by UV-vis studies. In addition, we show that the absorption maxima and optical band-gaps of azulenium cations can be tuned by the nature of the chromophore connected to the seven-membered ring of the azulene nucleus. This journal is

Original languageEnglish
Pages (from-to)4483-4489
Number of pages7
JournalChemical Science
Volume5
Issue number11
DOIs
Publication statusPublished - Nov 1 2014

ASJC Scopus subject areas

  • Chemistry(all)

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