Title

Hinged bis-porphyrin scaffolds I. The synthesis of a new porphyrin diene and its role in constructing hinged porphyrin dyads and cavity systems

RIS ID

29679

Publication Details

Tang, H., Dong, Z., Merican, Z., Margetic, D., Zeljko, M., Gunter, J., Officer, D. L., Butler, D. and Warrener, R. N. (2009). Hinged bis-porphyrin scaffolds I. The synthesis of a new porphyrin diene and its role in constructing hinged porphyrin dyads and cavity systems. Tetrahedron Letters, 50 (6), 667-670.

Abstract

Norbornene building BLOCKs formed by the reaction of porphyrin 1,3-dienes with norbornadiene or dimethyl tricyclo[4.2.1.0(2,5)]nona-2,7-diene-3,4-dicarboxylate were coupled with an ester-activated cyclobutene epoxide BLOCK to afford the first examples of hinged porphyrin-spacer-acceptor dyads. Similar dual coupling with a bis-(cyclobutene epoxide) formed doubly hinged POR-spacer-POR scaffolds separated by up to 16 sigma-bonds. The ability of the doubly hinged ZnPOR-16 sigma-ZnPOR scaffold to adopt cavity-shaped conformations was indicated by semiempirical AM1 calculations of these conformationally flexible bis-porphyrin scaffolds. (C) 2008 Elsevier Ltd. All rights reserved.

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Link to publisher version (DOI)

http://dx.doi.org/10.1016/j.tetlet.2008.11.109