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

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[<i>d</i>]thiazol-2-amine. This novel aza-BODIPY analogue forms a complementary hydrog...

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Bibliographic Details
Main Authors: Ru Feng, Zuoxu Chen, Yue Wang, Jianming Pan, Soji Shimizu
Format: Article
Language:English
Published: MDPI AG 2023-12-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/28/24/7940
Description
Summary: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[<i>d</i>]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.
ISSN:1420-3049