Strategies for the Synthesis of ‘Through-Space’ Chromophore Dimers Based on [2.2]Paracyclophane

Abstract

The evolution and motivation of regiospecific synthetic protocols for 4,7,12,15- donor and/or acceptor substitution of [2.2]paracyclophane is described. Analysis of protocols for the creation of molecules that model interchromophore contacts and delocalization from multiply brominated [2.2]paracyclophane is provided. Substrates that allow for Horner-Emmons coupling as an entry to high yield procedures for synthesizing chromophores built around tetrasubstituted [2.2]paracyclophane are described. Additionally, the synthesis of precursors for site-specific coupling and the resulting products of donor and acceptor substitution are presented. Brief representative examples of the unusual spectroscopic properties of the target compounds are given.

Key words

[2.2]paracyclophanes - through-space chromophore - Horner-Emmons reaction - site-specific coupling - donor/acceptor substitution

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11

‘Morphology’ in crystallography refers to the shape of the crystal with implications to the arrangement of subunits on the molecular scale. In organic electronics this term is extended to encompass intermolecular arrangements within non-crystalline or amorphous environments.

32

Zyss, J.; Ledoux, I.; Bartholomew, G. P.; Bazan, G. C.; Mukamel, S.; Volkov, S. work in progress.

33

Rumi, M.; Bartholomew, G. P.; Perry, J.; Bazan, G. C. work in progress.