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

文献情報

出版日 2021-09-10

DOI 10.1039/D1QO01169C

インパクトファクター 5.281

著者

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

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 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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