Self-assembled coordination cage as a reaction vessel: triplet sensitized [2+ 2] photodimerization of acenaphthylene, and [4+ 4] photodimerization of 9-anthraldehyde

Karthikeyan, S. ; Ramamurthy, V. (2005) Self-assembled coordination cage as a reaction vessel: triplet sensitized [2+ 2] photodimerization of acenaphthylene, and [4+ 4] photodimerization of 9-anthraldehyde Tetrahedron Letters, 46 (26). pp. 4495-4498. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2005.04.115

Abstract

Inner cavity of Pd-nanocage has been used as a reaction vessel for performing triplet sensitized [2+2] photodimerization of acenaphthylene using water soluble xanthene dyes (Eosin Y and Rose Bengal) as sensitizers, and [4+4] photodimerization of 9-anthraldehyde. Although the [4+4] photodimerization of 9-anthraldehyde gave similar results to solution reaction, the xanthene dye sensitized [2+2] triplet state photodimerization of acenaphthylene encapsulated within Pd-nanocage yielded the syn dimer in quantitative yield. The results obtained from the triplet state [2+2] photodimerization of acenaphthylene within Pd-nanocage is remarkable given the fact that the photodimerization reaction when performed in methanol in the presence of Eosin Y and Rose Bengal gave the syn and anti dimers in the ratio 0.5 and 0.6, respectively. Preaggregation of molecules encapsulated inside Pd-nanocage in a syn fashion seems to be the governing factor for such a behavior.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Pd-nanocage; Regioselectivity; Photodimerization; Acenaphthylene; 9-Anthraldehyde
ID Code:89994
Deposited On:04 May 2012 05:21
Last Modified:04 May 2012 05:21

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