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Photodimerization of coumarins in solid cyclodextrin inclusion complexes

Moorthy, Narasimha J and Venkatesan, K and Weiss, Richard G (1992) Photodimerization of coumarins in solid cyclodextrin inclusion complexes. In: Journal of Organic Chemistry, 57 (12). pp. 3292-3297.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo00038a012


The photodimerizations of coumarin and eight of its derivatives are found to proceed selectively in solid inclusion complexes with beta- and gamma-cyclodextrins (beta- and gamma-CD). The distribution of photodimers from these complexes is compared with those from the neat coumarin solids and their solutions in a variety of solvents. By assuming that the stereochemistry of the dimers reflects the packing arrangements of their precursors in the CD complexes, several hypotheses concering the locations and arrangements of the coumarins in the host toruses have been made. The stoichiometries of the complexes have been assigned on the basis of the presence or absence of photodimers and from NMR integration ratios of characteristic coumarin and saccharide protons. The relative orientations of substituted coumarins within a complex are inferred from the stereochemistry of the photodimers. Depending upon the substitution pattern of the coumarin molecules and the type of CD employed, complexes whose guest-host stoichiometries are 1:1, 2:1, and 2:2 have been identified. In several instances, dimers not available from irradiation of neat solid coumarins or their solutions have been obtained from the CD complexes.

Item Type: Journal Article
Publication: Journal of Organic Chemistry
Publisher: American Chemical Society
Additional Information: Copyright of this article belongs to American Chemical Society.
Keywords: Electron-Spin Resonance;Photochemical-Reactions;Photo-Dimerization;State;Micelles;Systems.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 02 May 2011 05:23
Last Modified: 02 May 2011 05:23
URI: http://eprints.iisc.ac.in/id/eprint/37310

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