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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