10.1021/ol102398y
The study presents an innovative iterative synthesis method for heterotelechelic oligo(phenylene-vinylene)s (OPVs) utilizing olefin cross-metathesis. This approach allows for the creation of oligomers with controlled lengths and paves the way for their assembly into repeating sequence copolymers (RSCs). The process is initiated by a cross-metathesis reaction between olefin-terminated oligomers and a vinylbenzaldehyde, yielding aldehyde-end-capped OPVs. These can then be transformed into metathesis-ready vinyl groups or used for further functionalization, such as the formation of donor-acceptor complexes. The study demonstrates the synthesis of various OPVs with different conjugation lengths, which exhibit tunable optical properties, and also explores the potential for creating complex copolymers through the conversion of OPVs into RSCs. The method's versatility is highlighted by the successful functionalization of OPVs and the potential for applying this metathesis-based coupling to phenylene monomers with a variety of substituents.