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The first calixarenequinhydrone: syntheses, self‐organized films and solvatochromism
Author(s) -
MeddebLimem Sondes,
Malezieux Bernard,
Herson Patrick,
BesbesHentati Salma,
Said Hechmi,
Blais JeanClaude,
Bouvet Marcel
Publication year - 2005
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.983
Subject(s) - chemistry , solvatochromism , absorption (acoustics) , mass spectrometry , salt (chemistry) , polymer , photochemistry , organic chemistry , molecule , optics , chromatography , physics
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, λ max varies from 627 nm in CHCl 3 to 677 nm in Et 2 O. 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.