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the challenge of synthesizing oligomers for molecular wires合成的寡聚物分子导线的挑战
Polymers 2011, 3, 545-557; doi:10.3390/polym3010545
OPEN ACCESS
polymers
ISSN 2073-4360
/journal/polymers
Article
The Challenge of Synthesizing Oligomers for Molecular Wires
Roar Søndergaard and Frederik C. Krebs *
RisøNational Laboratory for Sustainable Energy, Technical University of Denmark, Frederiksborgvej
399, DK-4000 Roskilde, Denmark; E-Mail: rosq@risoe.dtu.dk
* Author to whom correspondence should be addressed; E-Mail: frkr@risoe.dtu.dk;
Tel.: +45-4677-4799; Fax: +45-4677-4791.
Received: 17 January 2011; in revisedform: 6 February 2011 / Accepted: 23 February 2011 /
Published: 28 February 2011
Abstract: Controlling the size of the oligomer and introducing functional groups at the
ends of the oligomer that allow it to react with separate electrodes are critical issues when
preparing materials for molecular wires. We demonstrate a general synthetic approach to
oligophenylenevinylene (OPV) derivative molecules with a molecular length up to 9–10 nm
which allow for the introduction of aromatic thioacetate functionality in fully conjugated
oligomer systems. Oligomers containing 3–15 phenyl units were synthesized by step wise
Horner-Wadsworth-Emmons (HWE) reactions of a bifunctional OPV-monomer, which
demonstrated good control of the size of the OPVs. Workup after each reaction step
ensures a high purity of the final products. End group functionalization was introduced as a
last step.
Keywords: molecular wire; oligomer; oligophenylenevinylene; aromatic thioacetate
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