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

35 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
Externally publishedYes

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Oligomers
Cations
Substitution reactions
Protonation
Optical band gaps
Chromophores
Electronic properties
Optical properties
Color
Derivatives
Acids
azulene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Conjugated oligomers incorporating azulene building blocks-seven- vs. Five-membered ring connectivity. / Amir, Elizabeth; Murai, Masahito; Amir, Roey J.; Cowart, John S.; Chabinyc, Michael L.; Hawker, Craig J.

In: Chemical Science, Vol. 5, No. 11, 01.11.2014, p. 4483-4489.

Research output: Contribution to journalArticle

Amir, Elizabeth ; Murai, Masahito ; Amir, Roey J. ; Cowart, John S. ; Chabinyc, Michael L. ; Hawker, Craig J. / Conjugated oligomers incorporating azulene building blocks-seven- vs. Five-membered ring connectivity. In: Chemical Science. 2014 ; Vol. 5, No. 11. pp. 4483-4489.
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