Issue 60, 2019

aza-BODIPY synthesis towards vis/NIR functional chromophores based on a Schiff base forming reaction protocol using lactams and heteroaromatic amines

Abstract

aza-BODIPY is a class of heteroatom-containing BODIPY analogues targeting near infrared (NIR) chromophores and fluorophores. As a synthetic strategy towards aza-BODIPY structures, we have, recently, developed a Schiff base forming reaction using readily available lactams and heteroaromatic amines. Absorption and fluorescence of a series of compounds cover the whole range of the ultraviolet (UV)/visible (vis)/NIR regions. In addition, some compounds exhibit solid state emission, aggregation-induced emission enhancement, tunable fluorescence in the vis/NIR regions and non-linear optical properties. Furthermore, simple dimerization of aza-BODIPY chromophores caused unusual panchromatic absorption, whereas in combination with an N-confused porphyrin skeleton, multi-state NH tautomerism was achieved. In this Feature Article, wide applicability of this Schiff base forming reaction and optical and electrochemical properties of aza-BODIPY analogues thus synthesized are summarized including recent applications, such as bioimaging, photothermal cancer therapy and organic photovoltaics.

Graphical abstract: aza-BODIPY synthesis towards vis/NIR functional chromophores based on a Schiff base forming reaction protocol using lactams and heteroaromatic amines

Article information

Article type
Feature Article
Submitted
01 Mud 2019
Accepted
24 Kho 2019
First published
24 Kho 2019

Chem. Commun., 2019,55, 8722-8743

aza-BODIPY synthesis towards vis/NIR functional chromophores based on a Schiff base forming reaction protocol using lactams and heteroaromatic amines

S. Shimizu, Chem. Commun., 2019, 55, 8722 DOI: 10.1039/C9CC03365C

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