Anthracene-(aminomethyl)phenylboronic acid ester-immobilized glass substrates as fluorescent sensing materials based on photo-induced electron transfer for detection and visualization of water†

IF 3.5 Q2 CHEMISTRY, ANALYTICAL
Kazuki Tao, Keiichi Imato and Yousuke Ooyama
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Abstract

As a reversible and reusable fluorescent material possessing excellent durability for detecting and visualizing moisture and water droplets, we have designed and synthesized a PET (photo-induced electron transfer)-type fluorescent monomer KT-2 composed of anthracene fluorophore-(aminomethyl)-4-cyanophenylboronic acid pinacol ester (AminoMeCNPhenylBPin) with a 3-(triethoxysilyl)propyl group on the amino moiety and achieved preparation of drop-cast poly(KT-2-co-TEOS or GPTMS)silsesquioxane (SQ) films on glass substrates via the sol–gel reaction of KT-2 and tetraethoxysilane (TEOS) or (3-glycidyloxypropyl)trimethoxysilane (GPTMS). KT-2 exhibited enhancement of the fluorescence emission with the increase in water content in various solvents (less polar, polar, protic, and aprotic solvents) due to the formation of the PET inactive (fluorescent) species KT-2W by the interaction with water molecules. The detection limit (DL) of KT-2 for water in the low water content region below 1.0 wt% in the solvents was 0.015–0.020 wt%, indicating that KT-2 can act as a PET-type fluorescent sensor for a trace amount of water in solvents. Indeed, it was found that the poly(KT-2-co-TEOS or GPTMS)SQ films exhibited a reversible fluorescence off–on switching between the PET active state under a dry process and the PET inactive state under a wet process. Actually, the poly(KT-2-co-TEOS or GPTMS)SQ films initially exhibited a weak blue emission under a dry process but visually apparent blue emission upon exposure to moisture (under a wet process). In particular, the poly(KT-2-co-TEOS)SQ film displays superior reversible switching performance with a huge change in the fluorescence intensity in the dry–wet process compared with the poly(KT-2-co-GPTMS)SQ film. This result is attributed to the fact based on the measurements of water contact angles and the roughness on the film surfaces that the poly(KT-2-co-TEOS)SQ film with a pitted uneven structure has large amounts of KT-2 units on the surface which make it possible to form the PET inactive KT-2W structure by the interaction with water molecules. Herein, we propose that PET-type fluorescent sensor-immobilized glass substrates are one of the most promising and convenient functional dye materials based on a fluorescence off–on switching system for detecting and visualizing moisture and water droplets.

Abstract Image

基于光诱导电子转移的蒽-(氨甲基)苯硼酸酯固定化玻璃基板作为荧光传感材料,用于水的检测和可视化
作为一种可逆、可重复使用的荧光材料,它具有良好的耐久性,可用于检测和观察湿气和水滴、我们设计并合成了一种 PET(光诱导电子转移)型荧光单体 KT-2,该单体由蒽荧光团-(氨基甲基)-4-氰基苯硼酸频哪醇酯(AminoMeCNPhenylBPin)组成,氨基上带有 3-(三乙氧基硅基)丙基。(通过 KT-2 和四乙氧基硅烷(TEOS)或(3-缩水甘油氧丙基)三甲氧基硅烷(GPTMS)的溶胶-凝胶反应,在玻璃基底上制备出滴铸型聚(KT-2-co-TEOS 或 GPTMS)硅烷基二氧杂环戊烷(SQ)薄膜。)KT-2 在各种溶剂(弱极性溶剂、极性溶剂、质子溶剂和非质子溶剂)中的荧光发射随着含水量的增加而增强,这是由于与水分子的相互作用形成了 PET 非活性(荧光)物种 KT-2W。在溶剂中水份含量低于 1.0 wt% 的低水份含量区域,KT-2 对水份的检测限 (DL) 为 0.015-0.020 wt%,这表明 KT-2 可作为 PET 型荧光传感器检测溶剂中的痕量水份。事实上,研究发现聚(KT-2-co-TEOS 或 GPTMS)SQ 薄膜在干燥过程中的 PET 活性态和潮湿过程中的 PET 非活性态之间表现出可逆的荧光开关切换。实际上,在干燥过程中,聚(KT-2-co-TEOS 或 GPTMS)SQ 薄膜最初只发出微弱的蓝色荧光,而在受潮后(在湿润过程中)则发出明显的蓝色荧光。特别是,与聚(KT-2-co-GPTMS)SQ 薄膜相比,聚(KT-2-co-TEOS)SQ 薄膜在干湿过程中的荧光强度变化巨大,显示出卓越的可逆切换性能。这一结果归因于根据水接触角和薄膜表面粗糙度的测量结果得出的事实,即具有凹凸不平结构的聚(KT-2-co-TEOS)SQ 薄膜表面有大量的 KT-2 单元,这些单元通过与水分子的相互作用形成了 PET 非活性 KT-2W 结构。我们在此提出,基于荧光开关系统的 PET 型荧光传感器固定化玻璃基板是一种最有前景、最方便的功能性染料材料,可用于检测和观察湿气和水滴。
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