Synthesis of near-infrared absorbing and fluorescent bis(pyrrol-2-yl)squaraines and their halochromic properties

文献信息

发布日期 2021-09-10

DOI 10.1039/D1QO01169C

影响因子 5.281

作者

Yasuhiro Kubota, Masato Nakazawa, Junheon Lee, Ryoma Naoi, Motoki Tachikawa, Toshiyasu Inuzuka, Kazumasa Funabiki, Masaki Matsui, Taekyeong Kim

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摘要

1,3- and 1,2-Bis(pyrrol-2-yl)squaraines were easily and selectively synthesized. 1,2-Squaraines (partially conjugated neutral structure) showed blue-shifted λmax compared to the corresponding 1,3-squaraines (fully conjugated zwitterionic structure). Thiophene-fused 1,3-squaraine showed NIR absorption (781 nm) and fluorescence (833 nm). The λmax of thiophene-fused 1,3-squaraine was red-shifted to 1007 nm after mono-protonation and blue-shifted to 680 nm with di-protonation, suggesting that the mono-cationization of a linear π-conjugated structure bearing two terminal amino groups is an effective strategy for achieving a further red-shift in the λmax. A highly sensitive reusable acid gas sensing textile sensor was fabricated.

期刊推荐

Pharmacological Reviews

Journal of Heterocyclic Chemistry

Pure and Applied Chemistry

Journal of Physics and Chemistry of Solids

Journal of Catalysis

Kinetics and Catalysis

Molecular Pharmacology

Proceedings of the National Academy of Sciences of the United States of America

Nature

European Journal of Wood and Wood Products

来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Synthesis of near-infrared absorbing and fluorescent bis(pyrrol-2-yl)squaraines and their halochromic properties

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