TY - JOUR
T1 - An Electron-Accepting aza-BODIPY-Based Donor–Acceptor–Donor Architecture for Bright NIR Emission
AU - Kage, Yuto
AU - Kang, Seongsoo
AU - Mori, Shigeki
AU - Mamada, Masashi
AU - Adachi, Chihaya
AU - Kim, Dongho
AU - Furuta, Hiroyuki
AU - Shimizu, Soji
N1 - Funding Information:
This work was supported by Grants‐in‐Aid for Scientific Research (B) (JSPS KAKENHI Grant no. JP19H02703 and JP19H02790), Challenging Exploratory Research (JSPS KAKENHI Grant no. JP18K19081 and JP20K21227), Scientific Research on Innovative Areas, “π‐System Figuration: Control of Electron and Structural Dynamism for Innovative Functions (no. 2601)” (JSPS KAKENHI Grant no. JP15H01001 and JP17H05160), the Murata Science Foundation, and JSPS Fellows (JSPS KAKENHI Grand no. JP19J12257). Y.K. thanks the Kyushu University Leading Program for “Molecular System for Devices” from MEXT, Japan. The work at Yonsei University was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (No. 2020R1A5A1019141).
Publisher Copyright:
© 2021 Wiley-VCH GmbH
PY - 2021/3/17
Y1 - 2021/3/17
N2 - 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 5.2×104 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.
AB - 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 5.2×104 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.
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U2 - 10.1002/chem.202005360
DO - 10.1002/chem.202005360
M3 - Article
C2 - 33442895
AN - SCOPUS:85100976237
VL - 27
SP - 5259
EP - 5267
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 16
ER -