Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline Moiety

Ru Feng; Zuoxu Chen; Yue Wang; Jianming Pan; Soji Shimizu

doi:10.3390/molecules28247940

Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline Moiety

Molecules. 2023 Dec 5;28(24):7940. doi: 10.3390/molecules28247940.

Authors

Ru Feng^{1

2

3}, Zuoxu Chen¹, Yue Wang^{1

4}, Jianming Pan¹, Soji Shimizu^{2

5}

Affiliations

¹ School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, China.
² Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, Fukuoka 819-0395, Japan.
³ Jiangsu Chunlan Clean Energy Academy Co., Ltd., Taizhou 225300, China.
⁴ Jiangsu Agrochem Laboratory Co., Ltd., Changzhou 213022, China.
⁵ Center for Molecular Systems (CMS), Kyushu University, Fukuoka 819-0395, Japan.

Abstract

An asymmetric aza-BODIPY analogue bearing quinoxaline moiety was synthesized via a titanium tetrachloride-mediated Schiff-base-forming reaction of 6,7-dimethyl-1,4-dihydroquinoxaline-2,3-dione and benzo[d]thiazol-2-amine. This novel aza-BODIPY analogue forms a complementary hydrogen-bonded dimer due to the quinoxaline moiety in the crystal structure. It also shows intense absorption and fluorescence, with fluorescence quantum yields close to unity. The electrochemical measurements and the DFT calculations revealed the presence of the low-lying HOMO, which benefits their potential applications as an electron-transporting material.

Keywords: aza-BODIPY; fluorescence; hydrogen bonding; quinoxaline.

Abstract

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