Synthesis of near-infrared absorbing and fluorescent bis(pyrrol-2-yl)squaraines and their halochromic properties
Synthesis of near-infrared absorbing and fluorescent bis(pyrrol-2-yl)squaraines and their halochromic properties
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DOI：
10.1039/d1qo01169c
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发表时间：
2021-09-10
影响因子：
5.4
通讯作者：
Kim, Taekyeong
中科院分区：
文献类型：
--
作者：
Kubota, Yasuhiro;Nakazawa, Masato;Kim, Taekyeong
1，3-和1，2-双（吡咯-2-基）方酸菁的合成方法简单，选择性好。1，2-方酸菁（部分共轭的中性结构）与相应的1，3-方酸菁（完全共轭的两性离子结构）相比显示出蓝移的λ（max）。噻吩稠合的1，3-方酸显示NIR吸收（781 nm）和荧光（833 nm）。噻吩稠合的1，3-方酸的λ（max）在单质子化后红移到1007 nm，在双质子化后蓝移到680 nm，表明带有两个末端氨基的线性π共轭结构的单阳离子化是实现λ（max）进一步红移的有效策略。研制了一种可重复使用的高灵敏度酸性气体纺织传感器。
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 lambda(max) 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 lambda(max) 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 pi-conjugated structure bearing two terminal amino groups is an effective strategy for achieving a further red-shift in the lambda(max). A highly sensitive reusable acid gas sensing textile sensor was fabricated.