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Updated: Oct 14, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Synthesis of azulene fluorophores reveals structure-property relationships
Chiara Faverio1, João Gabriel Ribeiro1, Mehmet Kaplan1,2
1Department of Chemistry, University of Bath Bath BA2 7AY UK S.E.Lewis@bath.ac.uk.
Abstract:
We report the synthesis, photophysical characterisation, and crystallographic analysis of a series of substituted azulenes. The compounds are analogues of the known fluorophore diethyl 2-amino-6-hydroxyazulene-1,3-dicarboxylate, in which the electron-withdrawing groups at C1 and C3 have been retained, but the electron-donating groups at C2 and C6 have been systematically varied. Correlations were observed between the nature of the C2 and C6 substituents and the fluorescence quantum yields and emission maxima; on this basis trends in the structure-property relationship have been elucidated. A novel azulene exhibiting a five-fold increase in quantum yield over the previously known fluorophore has been identified.
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