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

Research output: Contribution to journalArticle

1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)8722-8743
Number of pages22
JournalChemical Communications
Volume55
Issue number60
DOIs
Publication statusPublished - Jan 1 2019

Fingerprint

Lactams
Schiff Bases
Chromophores
Amines
Infrared radiation
Optical properties
Fluorescence
Dimerization
Fluorophores
Porphyrins
Electrochemical properties
Agglomeration
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

@article{13be043678df4f81822f902fefddeb7b,
title = "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.",
author = "Soji Shimizu",
year = "2019",
month = "1",
day = "1",
doi = "10.1039/c9cc03365c",
language = "English",
volume = "55",
pages = "8722--8743",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "60",

}

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

PY - 2019/1/1

Y1 - 2019/1/1

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.

UR - http://www.scopus.com/inward/record.url?scp=85069769196&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85069769196&partnerID=8YFLogxK

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 -