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A Solution‐Processable meso ‐Phenyl‐BODIPY‐Based n ‐Channel Semiconductor with Enhanced Fluorescence Emission
Author(s) -
Ozcan Emrah,
Ozdemir Mehmet,
Ho Dongil,
Zorlu Yunus,
Ozdemir Resul,
Kim Choongik,
Usta Hakan,
Cosut Bunyemin
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201900317
Subject(s) - bodipy , intramolecular force , dihedral angle , acceptor , homo/lumo , photochemistry , fluorescence , semiconductor , quantum yield , materials science , intermolecular force , excited state , crystallography , band gap , chemistry , stereochemistry , molecule , optoelectronics , hydrogen bond , organic chemistry , atomic physics , condensed matter physics , physics , quantum mechanics
The molecular design, synthesis, and characterization of an acceptor‐donor‐acceptor (A‐D‐A) semiconductor BDY‐Ph‐2T‐Ph‐BDY comprising a central phenyl‐bithiophene‐phenyl π‐donor and BODIPY π‐acceptor end‐units is reported. The semiconductor shows an optical band gap of 2.32 eV with a highly stabilized HOMO/LUMO (−5.74 eV/−3.42 eV). Single‐crystal X‐ray diffraction (XRD) reveals D–A dihedral angle of ca. 66° and strong intermolecular “C−H ⋅⋅⋅ π (3.31 Å)” interactions. Reduced π‐donor strength, increased D–A dihedral angle, and restricted intramolecular D–A rotations allows for both good fluorescence efficiency (Φ F =0.30) and n ‐channel OFET transport (μ e =0.005 cm 2 /V ⋅ s; I on /I off =10 4 –10 5 ). This indicates a much improved (6‐fold) fluorescence quantum yield compared to the meso ‐thienyl BODIPY semiconductor BDY‐4T‐BDY. Photophysical studies reveal important transitions between locally excited (LE) and twisted intramolecular charge‐transfer (TICT) states in solution and the solid state, which could be controlled by solvent polarity and nano‐aggregation. This is the first report of such high emissive characteristics for a BODIPY‐based n ‐channel semiconductor.