Issue 6, 2011

Photodecaging from 9-substituted 2,7-dihydroxy and dimethoxyfluorenes: competition between heterolytic and homolytic pathways

Abstract

2,7-Dihydroxy-9-fluorenol (9), 2,7-dimethoxy-9-fluorenol (10), and 2,7-dimethoxy-9-acetoxyfluorene (11) were prepared and their photochemistry was studied in methanol and aqueous methanol solution in the hopes of observing efficient expulsion of the substituents positioned at the 9-position. For all three compounds, the primary photoproducts were 2,7-disubstituted-9-fluorenes and 2,7-disubstituted-9-methoxyfluorenes. A mechanism of reaction is proposed for production of these products, and involves competing homolytic and heterolytic pathways that produce radical and carbocation intermediates. Reaction quantum yields (for substrate disappearance) ranged between 0.21 and 0.31.

Graphical abstract: Photodecaging from 9-substituted 2,7-dihydroxy and dimethoxyfluorenes: competition between heterolytic and homolytic pathways

Article information

Article type
Paper
Submitted
19 Nov 2010
Accepted
06 Jan 2011
First published
10 Feb 2011

Photochem. Photobiol. Sci., 2011,10, 920-930

Photodecaging from 9-substituted 2,7-dihydroxy and dimethoxyfluorenes: competition between heterolytic and homolytic pathways

A. Roxin, A. Chase, E. Jeffers and M. Lukeman, Photochem. Photobiol. Sci., 2011, 10, 920 DOI: 10.1039/C0PP00351D

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