Synthesis of Naphthalene Diimide-Based Polymers for High Charge Transport Open Access

Saini, Shelly Rani (2017)

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This thesis is primarily aimed at the development of synthetic strategies for n-type semiconducting polymers based on the two important building blocks, namely, naphthalenediimide as electron acceptor material, and BODIPY as an electron donor material. NDI-based monomers and BODIPY donor monomers have demonstrated large implications in the field of organic semiconductors. When polymerized, these monomers have the potential to absorb light in the visible range, unlike other organic semiconducting materials that absorb mostly in the UV range. By decreasing the amount of high energy light entering the system for excitation, there should be an increase in efficiency in exciting from the HOMO to LUMO energy levels. We were able to successfully synthesize both the NDI and BODIPY monomers, as well as measure their absorption and emission spectra. Two polymers were synthesized, one in which the NDI monomers were copolymerized with thiophene units, and the other in which NDI and BODIPY monomers were copolymerized. While pNDI-BODIPY formed successfully, pNDI-bithiophene only formed oligomers due to a short polymerization time and dilute solution. The pNDI-BODIPY showed a notable red shift in absorption from the individual monomers. The NDI monomer and BODIPY monomers originally absorbed in the 390nm and 540nm range, respectively. After polymerization, the absorption shifted to the 400-580nm range of visible light, eliminating the absorption of high-energy UV light, due to an increase in conjugation of the polymer versus the monomer alone. In addition to the polymerization, previously reported synthetic methods were evaluated and modified to produce higher synthetic yields. In many cases, the modified synthetic protocols were efficient in producing high monomer yields.

Table of Contents

Table of Contents

Abstract (iv)

Acknowledgements (vi)

List of Figures (viii)

List of Schemes (ix)

List of Tables (x)

1. Background (1)

2. Synthesis and Characterization of NDI-thiophene Polymers (6)

i. Short-Chain NDI Monomer Synthesis (7)

ii. NDI-Bithiophene Polymer Synthesis (11)

3. Synthesis and Characterization of NDI-BODIPY Polymers (12)

i. Long-Chain NDI Monomer Synthesis (13)

ii. BODIPY Monomer Synthesis (17)

iii. NDI-BODIPY Polymer Synthesis (19)

4. Conclusion (23)

5. Experimental Methods (23)

References (30)

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