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An Electron‐Accepting aza‐BODIPY‐Based Donor–Acceptor–Donor Architecture for Bright NIR Emission
Author(s) -
Kage Yuto,
Kang Seongsoo,
Mori Shigeki,
Mamada Masashi,
Adachi Chihaya,
Kim Dongho,
Furuta Hiroyuki,
Shimizu Soji
Publication year - 2021
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.202005360
Subject(s) - triphenylamine , photochemistry , excited state , fluorescence , electroluminescence , bodipy , solvatochromism , chromophore , acceptor , materials science , ultrafast laser spectroscopy , electron donor , electron acceptor , absorption (acoustics) , chemistry , optoelectronics , atomic physics , spectroscopy , optics , layer (electronics) , nanotechnology , physics , biochemistry , condensed matter physics , quantum mechanics , composite material , catalysis
A bright near‐infrared (NIR) fluorescent molecule was developed based on the donor–acceptor–donor (D–A–D) approach using an aza‐BODIPY analog called pyrrolopyrrole aza‐BODIPY (PPAB) as an electron‐accepting chromophore. Directly introducing electron‐donating triphenylamine (TPA) to develop a D–A–D structure caused redshifts of absorption and emission of PPAB into the NIR region with an enhanced fluorescence brightness of up to 5.2×10 4 m −1 cm −1 , whereas inserting a phenylene linker between the TPA donor and the PPAB acceptor induced solvatochromic behavior in emission. Transient absorption spectra and theoretical calculations revealed the presence of a highly emissive hybridized locally excited and charge‐transfer state in the former case and the contribution of the dark charge‐separated state to the excited state in the latter case. The bright D–A–D PPAB as a novel emitter resulted in a NIR electroluminescence with a high external quantum efficiency of 3.7 % and a low amplified spontaneous emission threshold of ca. 80 μJ cm −2 , indicating the high potential for NIR optoelectronic applications.