TY - JOUR
T1 - Aza-BODIPY synthesis towards vis/NIR functional chromophores based on a Schiff base forming reaction protocol using lactams and heteroaromatic amines
AU - Shimizu, Soji
N1 - Funding Information:
This work was supported by Grants-in-Aid for Scientific Research (B) (JSPS KAKENHI Grant no. JP19H02703), a Grant-in-Aid for Challenging Exploratory Research (JSPS KAKENHI Grant no. JP18K19081) and the Scientific Research on Innovative Areas, ‘‘p-System Figuration: Control of Electron and Structural Dynamism for Innovative Functions (no. 2601)’’ (JSPS KAKENHI Grant no. JP15H01001 and JP17H05160) and ‘‘New Polymeric Materials Based on Element-Blocks (no. 2401)’’ (JSPS KAKENHI Grant no. 25102503 and JP15H00756).
Publisher Copyright:
© 2019 The Royal Society of Chemistry.
PY - 2019
Y1 - 2019
N2 - 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.
AB - 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.
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U2 - 10.1039/c9cc03365c
DO - 10.1039/c9cc03365c
M3 - Article
C2 - 31310253
AN - SCOPUS:85069769196
VL - 55
SP - 8722
EP - 8743
JO - Chemical Communications
JF - Chemical Communications
SN - 1359-7345
IS - 60
ER -