This presentation describes a novel class of poly(acetylene)-inspired organic semiconductors that combine the desirable conjugation lengths typical of polyenes (<i>e.g</i>. poly(acetylene)) with the desirable stability, processability, and chemical flexibility typical of polyaromatics (<i>e.g</i>. poly(thiophene)). This feature is relevant to many electronic device applications that rely on organic materials to adopt non-aromatic quinoidal forms under operationally-relevant scenarios, a transition that can only be realized by breaking aromaticity among repeat units. Our strategies eclipse the routine poly(arylene-vinylene, -butylene, and -ethynylene)-based systems studied to date by exploring conjugated (macro)molecules comprised of cyclopentadiene-based constituents that are devoid of aromatic stabilization energies yet topologically akin to many common aromatic heterocycles. Our investigations seek to provide a fundamental understanding of the structural features that govern the physicochemical properties of these systems, insight that will be used to establish knowledge-driven design criteria for high performance organic semiconductors with implications in the (opto)electronics device industries.

5,5-disubstituted cyclopentadiene-based conjugated macromolecules: Design, synthesis, and application

254th National Meeting (2017)

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