An Electron-Accepting aza-BODIPY-Based Donor–Acceptor–Donor Architecture for Bright NIR Emission

Yuto Kage, Seongsoo Kang, Shigeki Mori, Masashi Mamada, Chihaya Adachi, Dongho Kim, Hiroyuki Furuta, Soji Shimizu

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32 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)5259-5267
Number of pages9
JournalChemistry - A European Journal
Issue number16
Publication statusPublished - Mar 17 2021

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry


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