An iterative synthetic route toward pyrenophane chains

Williams, Kerry-Lynn M. (2015) An iterative synthetic route toward pyrenophane chains. Masters thesis, Memorial University of Newfoundland.

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Abstract

The use of pyrene as a building block for molecules with applications in optoelectronic devices is becoming increasingly important.1 In this regard, the development of methodologies that provide convenient and highly regioselective access to functionalized pyrenes will facilitate progress in this area. For example, the Bodwell group at Memorial University recently showed that the placement of alkoxy groups at the 4 and 5 positions on pyrene (e.g. 1) both activates the pyrene system towards electrophilic substitution and effectively hinders the 3 and 6 positions. This methodology has been used in the synthesis of (1,8-pyrenylene)-ethynylene macrocycles,2 and is now at the heart of an iterative five-step strategy aimed at the synthesis of oligomeric pyrenophanes 2, 3 and beyond. Details of the synthetic approach toward these pyrenophane chains will be presented. [illustration]

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