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Synlett 2006(18): 2879-2893  
DOI: 10.1055/s-2006-951526
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

The Heck Polycondensation for Functional Polymers

Youngu Lee, Yongye Liang, Luping Yu*
Department of Chemistry and James Frank Institute, The University of Chicago, 5735 S. Ellis Avenue, Chicago, Illinois 60637, USA
Fax: +1(773)7020805; e-Mail: lupingyu@uchicago.edu ;
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Publikationsverlauf

Received 11 April 2006
Publikationsdatum:
25. Oktober 2006 (online)

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Abstract

In this account, our own work in the synthesis of functionalized poly(p-phenylenevinylene)s (PPVs) for electrooptic applications via the Pd-catalyzed Heck polycondensation is summarized. It was shown that various functionalized PPVs could be synthesized by the Pd-catalyzed Heck reaction due to its mild reaction condition. These materials show interesting physical properties, ranging from non-linear optical effects, photorefractive effect, photovoltaic property to liquid crystallinity. These results demonstrate the versatile utility of the Heck reaction in synthesis of functional materials.

1 Introduction

2 Synthesis of Poly(p-phenylenevinylene)s (PPVs) by the Pd-Catalyzed Heck Reaction

2.1 Conjugated Liquid Crystalline Polymers

2.2 Synthesis of PPVs Functionalized with Non-Linear Optical (NLO) Chromophore

2.3 Regiospecifically Functionalized PPVs

3 Synthesis of PPVs Containing Metal Complexes by the Pd-Catalyzed Heck Reaction

3.1 Metalloporphyrin-Containing PPVs

3.2 Synthesis of PPVs Containing Ionic Transition-Metal ­Complexes

3.3 Conjugated Polymers Containing Mixed-Ligand ­Ruthenium(II) Complexes

4 Orthogonal Approach to Oligo(phenylenevinylene) and Phenylenevinylene Dendrimers and Synthesis of Diblock Copolymers

4.1 Stepwise Synthesis of Substituted Oligo(phenylene­vinylene) via an Orthogonal Approach

4.2 A Simple Orthogonal Approach to Phenylenevinylene ­Dendrimers

4.3 Synthesis of Diblock Copolymers Containing a Conjugated Block

5 Synthesis of Functionalized PPVs for Chemoselective ­Ligation

6 Conclusion

Key words

Heck reaction - palladium - polymers - conjugation - complexes