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Substituent electronic effects on the persistence and absorption spectra of (Z)-o-xylylenols. A nanosecond laser flash photolysis study
Authors:Koner Apurba L  Singhal Nidhi  Nau Werner M  Moorthy Jarugu Narasimha
Affiliation:Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India.
Abstract:[reaction: see text] A systematic investigation on a broad set of aldehydes reveals that the lifetimes of (Z)-photoenols can be modulated by variation of the substituents. We have found that the lifetimes of (Z)-enols (in benzene) can be varied by more than 1 order of magnitude with a judicious choice of the substituents that exert mesomeric and inductive effects as, for example, in the case of pentamethylbenzaldehyde (tau = 35 ns) and dicyanomesitaldehyde (tau = 760 ns). This study thus points to the fact that the electronic factors in conjunction with hydrogen bonding stabilization can considerably broaden the uni- as well as bimolecular chemistry based on photoenolization. Further, we have shown that the photoenols exhibit dramatic shifts in their absorption properties with variation of the substituents; although the photoenols have long been considered to be colored, their absorption properties have not been heretofore comprehensively examined.
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