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(Dibenzoylmethanato)boron Difluoride Derivatives Containing Triphenylamine Moieties: A New Type of Electron‐Donor/π‐Acceptor System for Dye‐Sensitized Solar Cells
Author(s) -
Mizuno Yosuke,
Yisilamu Yilihamu,
Yamaguchi Tomoya,
Tomura Masaaki,
Funaki Takashi,
Sugihara Hideki,
Ono Katsuhiko
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402010
Subject(s) - triphenylamine , homo/lumo , photochemistry , electron acceptor , cyclic voltammetry , acceptor , chemistry , electron donor , delocalized electron , redox , materials science , dye sensitized solar cell , boron , electrochemistry , inorganic chemistry , organic chemistry , molecule , electrolyte , physics , electrode , condensed matter physics , catalysis
(Dibenzoylmethanato)boron difluoride derivatives containing triphenylamine moieties were synthesized as a new type of electron‐donor/π‐acceptor system. These new compounds exhibited long‐wavelength absorptions in the UV/Vis spectra, and reversible oxidation and reduction waves in cyclic voltammetry experiments. Their amphoteric redox properties are based on their resonance hybrid forms, in which a positive charge is delocalized on the triphenylamine moieties and a negative charge is localized on the boron atoms. Molecular orbital (MO) calculations indicate that their HOMO and LUMO energies vary with the number of phenylene rings connected to the difluoroboron‐chelating ring. This is useful for optimizing the HOMO and LUMO levels to an iodine redox (I − /I 3 − ) potential and a titanium dioxide conduction band, respectively. Dye‐sensitized solar cells fabricated by using these compounds as dye sensitizers exhibited solar‐to‐electric power conversion efficiencies of 2.7–4.4 % under AM 1.5 solar light.