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Synthesis of Thieno[3,4‐ b ]thiophene‐Based Donor Molecules with Phenyl Ester Pendants for Organic Solar Cells: Control of Photovoltaic Properties via Single Substituent Replacement
Author(s) -
Wada Yuya,
Asada Yuki,
Ikai Tomoyuki,
Maeda Katsuhiro,
Kuwabara Takayuki,
Takahashi Kohshin,
Kanoh Shigeyoshi
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600205
Subject(s) - substituent , thiophene , organic solar cell , homo/lumo , conjugated system , molecule , polar effect , chemistry , electron donor , photochemistry , materials science , polymer chemistry , stereochemistry , organic chemistry , polymer , catalysis
We have synthesized novel thieno[3,4‐ b ]thiophene‐based π‐conjugated molecules with phenyl ester pendants as electron donor materials for solution‐processed organic photovoltaics (OPVs). As the electron‐withdrawing power of the p ‐substituent on the phenyl ester pendant in these molecules was enhanced, their highest occupied molecular orbital (HOMO) energy levels deepened by up to 0.3 eV. Accordingly, when OPV devices were fabricated from these materials, the open‐circuit voltage ( V oc ) was increased by up to 40 mV. A linear correlation was found to exist between the Hammett constants of the p ‐substituents and the HOMO levels of the molecules as well as the V oc of the corresponding OPV devices. The direct comparison with the corresponding benzyl ester‐type molecule demonstrated that an electronic influence of the single p ‐substituent on the pendant can be transmitted to the π‐conjugated backbones through a phenyl ester linkage to control the photovoltaic performances.