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Leveraging Coupled Solvatofluorochromism and Fluorescence Quenching in Nitrophenyl-Containing Thiazolothiazoles for Efficient Organic Vapor Sensing
Advanced Science ( IF 14.3 ) Pub Date : 2023-04-26 , DOI: 10.1002/advs.202205729 Andrew R Brotherton 1 , Abhishek Shibu 1 , Jared C Meadows 1 , Nickolas A Sayresmith 1 , Chloe E Brown 1 , Ana Montoya Ledezma 1 , Thomas A Schmedake 1 , Michael G Walter 1
Advanced Science ( IF 14.3 ) Pub Date : 2023-04-26 , DOI: 10.1002/advs.202205729 Andrew R Brotherton 1 , Abhishek Shibu 1 , Jared C Meadows 1 , Nickolas A Sayresmith 1 , Chloe E Brown 1 , Ana Montoya Ledezma 1 , Thomas A Schmedake 1 , Michael G Walter 1
Affiliation
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Solvatofluorochromic molecules provide strikingly high fluorescent outputs to monitor a wide range of biological, environmental, or materials-related sensing processes. Here, thiazolo[5,4-d]thiazole (TTz) fluorophores equipped with simple alkylamino and nitrophenyl substituents for solid-state, high-performance chemo-responsive sensing applications are reported. Nitroaromatic substituents are known to strongly quench dye fluorescence, however, the TTz core subtly modulates intramolecular charge transfer (ICT) enabling strong, locally excited-state fluorescence in non-polar conditions. In polar media, a planar ICT excited-state shows near complete quenching, enabling a twisted excited-state emission to be observed. These unique fluorescent properties (spectral shifts of 0.13 – 0.87 eV and large transition dipole moments Δµ = 20.4 – 21.3 D) are leveraged to develop highly sought-after chemo-responsive, organic vapor optical sensors. The sensors are developed by embedding the TTz fluorophores within a poly(styrene-isoprene-styrene) block copolymer to form fluorescent dye/polymer composites (ΦF = 70 – 97%). The composites respond reversibly to a comprehensive list of organic solvents and show low vapor concentration sensing (e.g., 0.04% solvent saturation vapor pressure of THF – 66 ppm). The composite films can distinguish between solvent vapors with near complete fluorescent quenching observed when exposed to their saturated solvent vapor pressures, making this an extremely promising material for optical chemo-responsive sensing.
中文翻译：
利用含硝基苯基噻唑并噻唑的偶联溶剂化荧光显色和荧光猝灭实现高效有机蒸气传感
溶剂化荧光变色分子提供惊人的高荧光输出，可监测各种生物、环境或材料相关的传感过程。在此，报道了配备简单烷基氨基和硝基苯基取代基的噻唑并[5,4-d]噻唑（TTz）荧光团，用于固态、高性能化学响应传感应用。众所周知，硝基芳香族取代基会强烈猝灭染料荧光，然而，TTz 核心巧妙地调节分子内电荷转移 (ICT)，从而在非极性条件下实现强烈的局部激发态荧光。在极性介质中，平面 ICT 激发态显示出接近完全猝灭，从而能够观察到扭曲的激发态发射。这些独特的荧光特性（0.13 – 0.87 eV 的光谱位移和大的跃迁偶极矩 Δ µ= 20.4 – 21.3 D) 用于开发备受追捧的化学响应有机蒸气光学传感器。该传感器是通过将 TTz 荧光团嵌入聚（苯乙烯-异戊二烯-苯乙烯）嵌段共聚物中形成荧光染料/聚合物复合材料（Φ F = 70 – 97%）而开发的。该复合材料对一系列有机溶剂可逆响应，并显示出低蒸气浓度传感（例如，THF 的 0.04% 溶剂饱和蒸气压 – 66 ppm）。当暴露在饱和溶剂蒸气压下时，复合薄膜可以区分溶剂蒸气，并观察到几乎完全的荧光猝灭，这使其成为光学化学响应传感的极有前途的材料。
更新日期：2023-04-26
中文翻译：
利用含硝基苯基噻唑并噻唑的偶联溶剂化荧光显色和荧光猝灭实现高效有机蒸气传感
溶剂化荧光变色分子提供惊人的高荧光输出，可监测各种生物、环境或材料相关的传感过程。在此，报道了配备简单烷基氨基和硝基苯基取代基的噻唑并[5,4-d]噻唑（TTz）荧光团，用于固态、高性能化学响应传感应用。众所周知，硝基芳香族取代基会强烈猝灭染料荧光，然而，TTz 核心巧妙地调节分子内电荷转移 (ICT)，从而在非极性条件下实现强烈的局部激发态荧光。在极性介质中，平面 ICT 激发态显示出接近完全猝灭，从而能够观察到扭曲的激发态发射。这些独特的荧光特性（0.13 – 0.87 eV 的光谱位移和大的跃迁偶极矩 Δ µ= 20.4 – 21.3 D) 用于开发备受追捧的化学响应有机蒸气光学传感器。该传感器是通过将 TTz 荧光团嵌入聚（苯乙烯-异戊二烯-苯乙烯）嵌段共聚物中形成荧光染料/聚合物复合材料（Φ F = 70 – 97%）而开发的。该复合材料对一系列有机溶剂可逆响应，并显示出低蒸气浓度传感（例如，THF 的 0.04% 溶剂饱和蒸气压 – 66 ppm）。当暴露在饱和溶剂蒸气压下时，复合薄膜可以区分溶剂蒸气，并观察到几乎完全的荧光猝灭，这使其成为光学化学响应传感的极有前途的材料。
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