Meso-pi-Extended/Deficient BODIPYs and Low-Band-Gap Donor-Acceptor Copolymers for Organic Optoelectronics
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info:eu-repo/semantics/closedAccessDate
2022Author
Can, AyseChoi, Gi-Seok
Ozdemir, Resul
Park, Soyoon
Park, Jin Su
Lee, Yongchul
Deneme, Ibrahim
Mutlugun, Evren
Kim, Choongik
Kim, Bumjoon J.
Usta, Hakan
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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.
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ACS APPLIED POLYMER MATERIALSVolume
4Issue
3URI
https://doi.org/10.1021/acsapm.1c01856?urlappend=%3Fref%3DPDF&jav=VoR&rel=cite-ashttps://hdl.handle.net/20.500.12573/1489