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Abstract: Organic electronics often use conjugated polymers to enable optoelectronic activity. It is a common practice to modify a polymer with alkyl side chains that improve its solubility so that solution processing can be used to make solid state samples. While this approach has proven useful, it introduces some additional issues: i) if the device contains multiple layers, any solution based pr... read moreocessing must not perturb already existing layers, and ii) the solubilizing side chains occupy space in the solid state with atoms that have no optoelectronic activity. This thesis describes a novel technique where conjugated polymers are functionalized with solubilizing side chains that can be removed by irradiating the polymer with ultraviolet light. Chapter 2 describes the use of photocleavable o-nitrobenzyl (NB) ester solubilizing side chains on a polythiophene backbone. This methodology works in both solution leading to aggregation, and in the solid state leading to an insoluble film. Prior work on changing the solubility of polythiophene relied on using heat as the external stimulus to initiate the side chain cleavage. Chapter 3 describes the further exploration of NB side chains on polythiophene. This work examines the modification of the NB group to increase the rate of photocleavage, the use of donor-accepter polymer backbones, and patterning. Finally, Chapter 4 describes the application of this methodology to new low-bandgap conjugated polymers that absorb light in the near-infrared (NIR) region.
Thesis (Ph.D.)--Tufts University, 2015.
Submitted to the Dept. of Chemistry.
Advisor: Samuel Thomas.
Committee: Clay Bennett, Elena Rybak-Akimova, and Erik Berda.
Keywords: Organic chemistry, and Polymer chemistry.read less
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