Since the first report on the solid-state preparation of polydiacetylene (PDA) in 1969, extensive research efforts have been devoted to this classic type of conjugated polymers. PDAs have found widespread applications in non-linear optics, organic conductors and sensory materials. Despite a large number of examples, PDAs reported to date have been synthesized exclusively from a single type of reaction, i.e. irradiation induced topochemical polymerization of diacetylene (DA) monomers. Such reactions occur efficiently only if the DA monomers are able to pack into periodic structures within very strict geometrical boundaries. As a result, few types of DA monomers, typically having alkyl spacers between DA cores and functional side-groups, can be successfully polymerized.We report herein novel polydiacetylenes (PDAs) bearing alkyl and phenyl substituents synthesized, for the first time, by solution polymerization using acyclic enediyne metathesis. The resulting polymers are soluble in common organic solvents and show distinct physical and photophysical properties both in solutions and as thin films, caused by different steric and electronic effects from the side-groups. Bulk heterojunction solar cells employing these PDAs have been fabricated and evaluated, which out-performed, by more than 100 fold, the only previous example of solar cells employing PDAs from solid-state polymerization. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/240nm/uploads/35004_acs_fall_2010_figure.jpg' alt='' />

Solution processable polydiacetylenes (PDAs) through acyclic enediyne metathesis polymerization

247th National Meeting (2014)

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