Date of Award

5-1-2014

Degree Name

Master of Science

Department

Chemistry

First Advisor

Plunkett, Klye

Abstract

This thesis is based on a research project aimed at creating new electron acceptors from cyclopenta-fused polycyclic hydrocarbons (CP-PAHs). We have utilized Pd-catalyzed cyclopentenelation reactions to create 2,7-bis(trimethylsilyl)cyclopenta[hi]aceanthrylene 1 and 2,7-dibromocyclopenta[hi]aceanthrylene 3. Upon bromination these fullerene fragments serve as a building block for creating both small-molecule and polymeric electron acceptors. The resulting materials are dark green and possess narrow band gaps with low-lying lowest occupied molecular orbitals (LUMO). A fluorescence quenching at poly(3-heylthiophene) demonstrates the electron accepting behaviors of the materials. Traditional semiconductors are integrated with an CP-PAH core creating small molecules (or small molecules are created consisting of a CP-PAH core, complementary semiconductor, and aromatic substituents).

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