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Regioisomeric Polythiophene Derivatives: Synthesis and Structure-Property Relationships for Organic Electronic Devices

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Abstract

Three types of tail-to-tail (PDCBTTT), head-to-tail (PDCBTHT), and head-to-head (PDCBTHH) regioisomeric polythiophene copolymers were synthesized by modification of the substitution positions of their alkoxycarbonyl side-chains. Chain conformation, and optical, electrochemical, morphological, and charge-transport characteristics of the polymers were significantly influenced by their regiochemistry. PDCBTHH showed an amorphous morphology due to strong steric hindrance between its head-to-head alkoxycarbonyl side-chains, resulting in the poorest performance in organic solar cells and transistors among three types. PDCBTHT had a regiorandom structure with both head-to-tail and tail-to-head linkages in a polymer chain. As determined by field-effect mobility measurements, a highly regioregular and planar PDCBTTT exhibited the highest hole mobility (μ = 0.065 cm2 V-1s-1), which was two orders of magnitude higher than that of the regiorandom PDCBTHT. The highest photovoltaic performance was also measured for PDCBTTT:a fullerene acceptor (PC71BM), by maintaining the packed structures of pristine PDCBTTT polymers in the blend with PC71BM. Altering the topology of alkoxycarbonyl side-chains of the copolymers resulted in significant differences in crystalline morphologies and electrical properties and thus should be carefully considered in the molecular design of organic semiconductors.

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Author notes

  1. These authors equally contributed to this work.

Authors and Affiliations

  1. Department of Chemistry, Korea University, Seoul, 02841, Korea

    Young Woong Lee, Kawon Pak & Han Young Woo

  2. Department of Energy Engineering, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST-gil, Ulju-gun, Ulsan, 44919, Korea

    Song Yi Park, Na Gyeong An & Jin Young Kim

  3. Division of Chemical Engineering, Dongseo University, 47, Jurye-ro, Sasang-gu, Busan, 47011, Korea

    Junghoon Lee

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  1. Young Woong Lee
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Correspondence to Jin Young Kim or Han Young Woo.

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Acknowledgments: This work was supported by the National Research Foundation (NRF) of Korea (Grants NRF-2019R1A2C2085290, 2019R1A6A1A11044070, 2019M1A2A2065614, 2015M1A2A2057506).

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Lee, Y.W., Pak, K., Park, S.Y. et al. Regioisomeric Polythiophene Derivatives: Synthesis and Structure-Property Relationships for Organic Electronic Devices. Macromol. Res. 28, 772–781 (2020). https://doi.org/10.1007/s13233-020-8097-x

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  • DOI: https://doi.org/10.1007/s13233-020-8097-x

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