Insertion−Coupling−Cycloisomerization Domino Synthesis and Cation-Induced Halochromic Fluorescence of 2,4-Diarylpyrano[2,3-b]indoles

2,4-Diarylpyrano[2,3-b]indoles are formed via a Pd−Cu-catalyzed insertion−coupling−cycloisomerization domino reaction in moderate yields. Although the tricyclic systems are nonfluorescent in solution, protonation, quaternation, or complexation with metal ions induces intense green luminescence. Most...

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Bibliographic Details
Published in:Organic letters 2010-09, Vol.12 (18), p.4122-4125
Main Authors: Schönhaber, Jan, Frank, Walter, Müller, Thomas J. J
Format: Article
Language:English
Subjects:
Cations - chemistry
Crystallography, X-Ray
Cyclization
Fluorescent Dyes - chemical synthesis
Indoles - chemistry
Isomerism
Methylation
Models, Molecular
Molecular Structure
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Summary:2,4-Diarylpyrano[2,3-b]indoles are formed via a Pd−Cu-catalyzed insertion−coupling−cycloisomerization domino reaction in moderate yields. Although the tricyclic systems are nonfluorescent in solution, protonation, quaternation, or complexation with metal ions induces intense green luminescence. Most strikingly, selective halochromic fluorescence of zinc and magnesium over calcium ions classify the title compounds as metal-selective luminescence sensors.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101709p