Multifunctional properties of monodisperse end-functionalized oligophenylenevinylenes
M. S. Wong and Z. H. Li
Department of Chemistry, Hong Kong Baptist University,
Kowloon Tong, Hong Kong SAR, China
Abstract: Novel series of monodisperse, end-functionalized oligophenylenevinylenes
(OPVs) containing up to eight phenyl rings have been designed and synthesized
by a convergent approach using the stereoselective Wadsworth�Emmons
reactions for an investigation of technologically useful functional
properties. According to PM3 semiempirical quantum mechanical calculations,
the frontier molecular orbitals and the energy gap of an OPV could be
shifted or tuned by the functional substituent(s) that are incorporated
as end-caps. Our theoretical and experimental evidences have shown that
the end-substituents of an oligomer do not affect coplanarity of the
pi-conjugated system. It has also been found that the newly synthesized
OPVs can exhibit various useful functional properties such as light-emitting
properties, photovoltaic effects, third-order nonlinear optical responses,
and chemical sensing properties depending on the nature of the end-substituents.
In this contribution, the structural factor(s) that can enhance a specific
functional property of a molecule or material will be discussed.
*Lecture presented at the symposium "Polymers in electronics
and photonics: Synthesis, characterizations and device applications",
as part of the 39th IUPAC Congress and 86th Conference of the Canadian
Society for Chemistry: Chemistry at the Interfaces, Ottawa, Canada,
10-15 August 2003. Other Congress presentations are published in this
issue, pp. 1295-1603.
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