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Precise Electron-Withdrawing Strength Modulation of ESIPT Probes for Ultrasensitive and Specific Fluorescence Sensing
Analytical Chemistry ( IF 6.7 ) Pub Date : 2023-06-01 , DOI: 10.1021/acs.analchem.3c01120 Yanwen Guo 1 , Zhenzhen Cai 2 , Fei Yan 2 , Da Lei 2 , Yanan Guo 2 , Shuhai Zhang 1 , Xincun Dou 1, 2, 3
Analytical Chemistry ( IF 6.7 ) Pub Date : 2023-06-01 , DOI: 10.1021/acs.analchem.3c01120 Yanwen Guo 1 , Zhenzhen Cai 2 , Fei Yan 2 , Da Lei 2 , Yanan Guo 2 , Shuhai Zhang 1 , Xincun Dou 1, 2, 3
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The precise regulation of the electron-withdrawing/electron-donating strength in a probe is of great significance for the design of reaction-based fluorescent probes with specific functionalities. Here, a family of excited-state intramolecular proton transfer (ESIPT)-based probes with fluorescence turn-on sensing properties toward KMnO4 was designed by precisely modulating the electron-withdrawing strength of the substituents located at the para-position of the recognition group. It is found that −F, −CHO, and −H as the electron-withdrawing groups bound at the probe can specifically recognize KMnO4, which ensures a blue emission displayed by the reaction products. Especially with −CHO as the electron-withdrawing group, the reaction product shows the most stable fluorescence. The probe 2-(benzo[d]oxazol-2-yl)-4-formylphenyl acrylate (BOPA-CHO) demonstrated a more superior sensing performance toward KMnO4, including a low limit of detection (LOD, 0.96 nM), a rapid response (<3 s), and a rather good selectivity even in the presence of 21 interferents. Moreover, the practicality of the probe was further verified by a test pen comprising a BOPA-CHO-embedded sponge, which is capable of detecting KMnO4 solid with a naked-eye LOD of 11.62 ng. The present probe design and modulation strategy would open up a new path for the design of high-performance fluorescent probes.
中文翻译：
用于超灵敏和特定荧光传感的 ESIPT 探针的精确吸电子强度调制
探针中吸电子/给电子强度的精确调节对于设计具有特定功能的基于反应的荧光探针具有重要意义。在这里，通过精确调节位于识别基团对位的取代基的吸电子强度，设计了一系列基于激发态分子内质子转移 (ESIPT) 的探针，这些探针具有对 KMnO 4 的荧光开启传感特性. 发现-F、-CHO、-H作为结合在探针上的吸电子基团可以特异性识别KMnO 4, 这确保了反应产物显示的蓝色发射。尤其是-CHO作为吸电子基团时，反应产物显示出最稳定的荧光。探针 2-(benzo[ d ]oxazol-2-yl)-4-formylphenyl acrylate (BOPA-CHO) 对 KMnO 4表现出更优异的传感性能，包括低检测限（LOD，0.96 nM），快速检测响应 (<3 s)，即使在存在 21 种干扰物的情况下也具有相当好的选择性。此外，该探针的实用性通过包含BOPA-CHO嵌入海绵的测试笔进一步验证，该测试笔能够检测KMnO 4固体，肉眼 LOD 为 11.62 ng。目前的探针设计和调制策略将为高性能荧光探针的设计开辟一条新途径。
更新日期：2023-06-01
中文翻译：
用于超灵敏和特定荧光传感的 ESIPT 探针的精确吸电子强度调制
探针中吸电子/给电子强度的精确调节对于设计具有特定功能的基于反应的荧光探针具有重要意义。在这里，通过精确调节位于识别基团对位的取代基的吸电子强度，设计了一系列基于激发态分子内质子转移 (ESIPT) 的探针，这些探针具有对 KMnO 4 的荧光开启传感特性. 发现-F、-CHO、-H作为结合在探针上的吸电子基团可以特异性识别KMnO 4, 这确保了反应产物显示的蓝色发射。尤其是-CHO作为吸电子基团时，反应产物显示出最稳定的荧光。探针 2-(benzo[ d ]oxazol-2-yl)-4-formylphenyl acrylate (BOPA-CHO) 对 KMnO 4表现出更优异的传感性能，包括低检测限（LOD，0.96 nM），快速检测响应 (<3 s)，即使在存在 21 种干扰物的情况下也具有相当好的选择性。此外，该探针的实用性通过包含BOPA-CHO嵌入海绵的测试笔进一步验证，该测试笔能够检测KMnO 4固体，肉眼 LOD 为 11.62 ng。目前的探针设计和调制策略将为高性能荧光探针的设计开辟一条新途径。
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