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Electroluminescence and fluorescence response towards acid vapors depending on the structures of indole-fused phospholes

机译:取决于吲哚稠合的磷脂的结构,对酸蒸汽的电致发光和荧光响应

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摘要

New isomers of phosphole heteroacenes 2-DIPO and 3-DIPO, in which indoles were fused with phospholes in different manners, have been synthesized. It is found that 2-DIPO containing the 5,6-dihydrophospholo[3,2-b:4,5-b']diindole skeleton is highly emissive in solution and in solid state, but the emission of 3-DIPO bearing 5,7-dihydrophospholo[2,3-b:5,4-b']diindole is weak because the emission of 2-DIPO and 3-DIPO is originated from pi*-pi and pi*-n transitions, respectively. The OLED using 2-DIPO as emitter exhibits better performance than that based on 3-DIPO on account of the poor emission of 3-DIPO. It is interesting that the filter paper strip containing 2-DIPO could detect gaseous strong acid by naked eye. For example, the emitting color of the test paper changes from green to yellow upon exposure to HCl vapor, and can recover upon exposure to gaseous NH3. This is the first example of a fluorescence sensor probe based on phosphole to detect acid vapors. However, acid cannot induce the change of the emission for 3-DIPO due to the steric effect of neighboring groups of N-CH3 and benzene around P=O to prevent the formation of H-bonding between acid and P=O in 3-DIPO.
机译:合成了磷酸杂杂烃2-DIPO和3-DIPO的新异构体,其中吲哚以不同方式与磷脂融合。发现含有5,6-二氢膦基[3,2-b:4,5-b']二吲哚骨架的2-DIPO在溶液和固态下均具有高发射率,但是带有3-DIPO的发射是5, 7-二氢膦基[2,3-b:5,4-b']二吲哚很弱,因为2-DIPO和3-DIPO的发射分别来自pi * -pi和pi * -n跃迁。由于3-DIPO的发射不良,因此使用2-DIPO作为发射器的OLED表现出比基于3-DIPO的OLED更好的性能。有趣的是,含有2-DIPO的滤纸条可以用肉眼检测到气态强酸。例如,试纸的发射颜色在暴露于HCl蒸气时从绿色变为黄色,并且在暴露于气态NH3时可以恢复。这是基于用于检测酸性蒸气的磷脂的荧光传感器探针的第一个示例。但是,由于N = CH3和P = O附近的苯的相邻基团的空间效应,酸不能诱导3-DIPO的发射变化,从而防止3-DIPO中酸和P = O之间形成H键。

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