Photochromic Lactone-Fused Phenanthropyrans with Broad Absorption and Rapid Color Change

New lactone-fused phenanthrol[1,2-b]pyrans were successfully synthesized in 4 steps from naphthaldehydes using, as the key step, the acid-catalyzed cascade condensation of methyl 1-hydroxyphenanthrene-3-carboxylates with diarylbut-2-yne-1,4-diols, which forms the pyran and lactone rings. After expos...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2022-08, Vol.95 (8), p.1272-1279
Main Authors: Graça, Vânia, Sousa, Céu M, Coelho, Paulo J
Format: Article
Language:English
Subjects:
Carboxylates
Chloroform
Color
Diols
Room temperature
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Summary:New lactone-fused phenanthrol[1,2-b]pyrans were successfully synthesized in 4 steps from naphthaldehydes using, as the key step, the acid-catalyzed cascade condensation of methyl 1-hydroxyphenanthrene-3-carboxylates with diarylbut-2-yne-1,4-diols, which forms the pyran and lactone rings. After exposing CHCl3 solutions of these polyaromatic compounds to UV or sunlight, at room temperature, the color changes vividly from slightly yellow to deep red/brown in a matter of seconds, and fades spontaneously, in the dark, within 1.5 min.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20220144