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    Meso-pi-Extended/Deficient BODIPYs and Low-Band-Gap Donor-Acceptor Copolymers for Organic Optoelectronics
    (AMER CHEMICAL SOC, 2022) Can, Ayse; Choi, Gi-Seok; Ozdemir, Resul; Park, Soyoon; Park, Jin Su; Lee, Yongchul; Deneme, Ibrahim; Mutlugun, Evren; Kim, Choongik; Kim, Bumjoon J.; Usta, Hakan; 0000-0002-7957-110X; 0000-0003-3715-5594; 0000-0002-0618-1979; 0000-0001-9415-0242; AGÜ, Mühendislik Fakültesi, Malzeme Bilimi ve Nanoteknoloji Mühendisliği Bölümü; Can, Ayse; Ozdemir, Resul; Mutlugun, Evren; Deneme, Ibrahim; Usta, Hakan
    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 πacceptor 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-πextension strategy to realize BODIPYs with favorable π-acceptor properties, and our findings could open up future materials design avenues in various organic optoelectronic applications.