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Photoreactions of 1,8-Anthrylene-ethynylene Acyclic Oligomers

Shinji Toyota ,  Makoto Kuga ,  Michio Goichi 

Department of Chemistry, Okayama University of Science, 1-1 Ridaicho, Okayama 700-0005, Japan

Abstract
We reported the synthesis of structure of 1,8-anthrylene-ethynylene cyclic tetramer 1, which featured the diamond prism structure with two pairs of parallel oriented anthracene group [1]. This macrocyclic compound gave no significant products upon UV irradiation because of the structural constrain. Similar photoreactions were carried out with acyclic oligomers to investigate the relation between the conformational mobility and the reactivity.

Trimer 2 was prepared by the Sonogashira coupling between 1,8-diiodoanthracene and singly silylated 1,8-diethynylanthracene. Compound 2 gave a single product Upon UV irradiation (>420 nm) in benzene, where the anthracene groups at the both ends underwent [4+4]photocyclization. Since this product was enantiomerically resolved by chiral HPLC, its structure was established to be the chiral form 3, which resulted from cyclization in the anti-form rather than the syn-form. This photo-product was reversibly converted to the original oligomer upon heating it at 180 °C. Details of the reversibly processes, chiroptical properties of enantiopure 3, and some attempts of photoreactions of an acyclic tetramer will be reported.

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[1] S. Toyota, M. Goichi, M. Kotani, Angew. Chem. Int. Ed. 2004, 43, 2248.

 

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Related papers

Presentation: poster at 18th Conference on Physical Organic Chemistry, Posters, by Shinji Toyota
See On-line Journal of 18th Conference on Physical Organic Chemistry

Submitted: 2006-05-25 01:17
Revised:   2009-06-07 00:44