The first calixarenequinhydrone: syntheses, self-organized films and solvatochromism

Di(methoxy‐p‐tert‐butyl)calix[4]arenediquinone (2) was prepared from di(methoxy‐p‐tert‐butyl)calix[4]arene. Reduction of 2 led to its calix[4]arenedihydroquinone analog 3. Partial reduction of 2 by 0.5 equiv. of a reducing agent led to the calix[4]arenequinhydrone charge‐transfer complex 4, which ex...

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Bibliographic Details
Published in:Journal of physical organic chemistry 2005-12, Vol.18 (12), p.1176-1182
Main Authors: Meddeb-Limem, Sondes, Malezieux, Bernard, Herson, Patrick, Besbes-Hentati, Salma, Said, Hechmi, Blais, Jean-Claude, Bouvet, Marcel
Format: Article
Language:English
Subjects:
calixarene
charge-transfer complex
quinhydrone
quinone
self-organization
solvatochromism
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Summary:Di(methoxy‐p‐tert‐butyl)calix[4]arenediquinone (2) was prepared from di(methoxy‐p‐tert‐butyl)calix[4]arene. Reduction of 2 led to its calix[4]arenedihydroquinone analog 3. Partial reduction of 2 by 0.5 equiv. of a reducing agent led to the calix[4]arenequinhydrone charge‐transfer complex 4, which exhibits an intense solvatochromic absorption band in the visible region. Thus, λmax varies from 627 nm in CHCl3 to 677 nm in Et2O. The association between two moieties of calix[4]arenequinonehydroquinone disodium salt was evidenced by matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry. The optical absorptions of 4 and a quinhydrone‐containing polymer were compared. A calix[4]arenequinonecyclohexadienone derivative was also obtained and characterized by X‐ray diffraction. Copyright © 2005 John Wiley & Sons, Ltd. Partial reduction of calix[4]arenediquinone led to the calix[4]arenequinhydrone charge‐transfer complex, which exhibits an intense solvatochromic absorption band in the visible region. A calixarenequinonecyclohexadienone derivative was also reported and characterized by X‐ray diffraction.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.983