Shimizu Soji
Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 819-0395, Japan.
Chem Commun (Camb). 2019 Jul 23;55(60):8722-8743. doi: 10.1039/c9cc03365c.
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.
氮杂硼二吡咯是一类含杂原子的硼二吡咯类似物，可作为近红外（NIR）发色团和荧光团。作为一种构建氮杂硼二吡咯结构的合成策略，我们最近开发了一种利用易得的内酰胺和杂芳族胺形成席夫碱的反应。一系列化合物的吸收和荧光覆盖了紫外（UV）/可见（vis）/近红外（NIR）区域的整个范围。此外，一些化合物表现出固态发射、聚集诱导发射增强、可见/近红外区域的可调荧光以及非线性光学性质。此外，氮杂硼二吡咯发色团的简单二聚化导致了异常的全色吸收，而与N-稠合卟啉骨架结合时，则实现了多态NH互变异构。在这篇专题文章中，总结了这种席夫碱形成反应的广泛适用性以及由此合成的氮杂硼二吡咯类似物的光学和电化学性质，包括最近的应用，如生物成像、光热癌症治疗和有机光伏。
