Meso-π-Extended/Deficient BODIPYs and Low-Band-Gap Donor-Acceptor Copolymers for Organic Optoelectronics

Can A., Choi G., ÖZDEMİR R., Park S., Park J. S., Lee Y., ...More

ACS Applied Polymer Materials, vol.4, no.3, pp.1991-2005, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 4 Issue: 3
  • Publication Date: 2022
  • Doi Number: 10.1021/acsapm.1c01856
  • Journal Name: ACS Applied Polymer Materials
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Compendex
  • Page Numbers: pp.1991-2005
  • Keywords: conjugated polymers, BODIPY, organic solar cells, organic semiconductors, LUMO, POLYMER SOLAR-CELLS, CHANNEL SEMICONDUCTORS, MECHANICALLY ROBUST, CONJUGATED POLYMERS, ELECTRON-DONOR, ENERGY-LEVELS, PERFORMANCE, POLY(3-HEXYLTHIOPHENE), THIAZOLE
  • Kayseri University Affiliated: No

Abstract

© 2022 American Chemical Society.The realization of π-deficient acceptors and their donor-acceptor copolymers has become a key research focus for the realization of versatile organic optoelectronic materials and devices. Herein, we demonstrate the theoretical design, synthesis, and physicochemical/optoelectronic characterization of two meso-π-extended/deficient BODIPY building blocks (2OD-T2BDY and 2OD-TTzBDY) and a library of donor-acceptor copolymers with low band gap (Eg = 1.30-1.35 eV) based on these building blocks. These building blocks, to the best of our knowledge, are the first examples of BODIPYs with meso-π-extension. A library of BODIPY building blocks with varied meso units/substituents is studied to reveal the meso effects on the semiconducting BODIPY’s optoelectronic properties. The building blocks showed favorable π-acceptor electronic/structural properties with meso-π-delocalized and stabilized LUMOs (ca. −3.6 eV) and large ground-state dipole moments of 4.9-5.5 D. Consistent with the theoretical/experimental π-electronic structures, all copolymers functioned as p-type semiconductors in field-effect transistors and as donor materials in the bulk heterojunction organic photovoltaics. Power conversion efficiencies of up to 4.4% with a short-circuit current of 12.07 mA cm-2 were achieved. This study demonstrates a unique meso-π-extension strategy to realize BODIPYs with favorable π-acceptor properties, and our findings could open up future materials design avenues in various organic optoelectronic applications.