Synthesis of naphthalene-fused imidazo[1,2-a]pyridinium salts showing green luminescence with high quantum yields and large Stokes shift

Sota Abe; Tetsuro Katayama; Akihiro Furube; Atsushi Tabata; Yasushi Yoshida; Shoko Ueta; Yukihiro Arakawa; Keiji Minagawa; Yasushi Imada; Fumitoshi Yagishita

doi:10.1039/D5OB00447K

Synthesis of naphthalene-fused imidazo[1,2-a]pyridinium salts showing green luminescence with high quantum yields and large Stokes shift†

Sota Abe,^a Tetsuro Katayama,*^b Akihiro Furube,

^b Atsushi Tabata,^c Yasushi Yoshida,

^d Shoko Ueta,^a Yukihiro Arakawa,

^a Keiji Minagawa,^a Yasushi Imada

^a and Fumitoshi Yagishita

*^ab

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* Corresponding authors

^a Department of Applied Chemistry, Tokushima University, 2-1 Minamijosanjima, Tokushima 770-8506, Japan
E-mail: yagishitaf@tokushima-u.ac.jp

^b Institute of Post-LED Photonics, Tokushima University, 2-1 Minamijosanjima, Tokushima 770-8506, Japan

^c Department of Bioscience and Bioindustry, Tokushima University, 2-1 Minamijosanjima, Tokushima 770-8513, Japan

^d Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Chiba 263-8522, Japan

Abstract

We have synthesized naphthalene-fused imidazo[1,2-a]pyridines by a novel electrophilic iodocyclization of 2-alkynyl-3-arylimidazo[1,2-a]pyridines. Notably, their quaternized salts exhibited green emission with unexpectedly high quantum yields and mega-large Stokes shift and were successfully used for mitochondrial imaging.

Organic & Biomolecular Chemistry

Synthesis of naphthalene-fused imidazo[1,2-a]pyridinium salts showing green luminescence with high quantum yields and large Stokes shift†

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Synthesis of naphthalene-fused imidazo[1,2-a]pyridinium salts showing green luminescence with high quantum yields and large Stokes shift

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