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The influence of amino substituents on the signal‐output, selectivity, and sensitivity of a hydroxyaromatic 1,2,3‐triazolyl chemosensor for anions—A structure–property relationship investigation
Journal of Physical Organic Chemistry ( IF 1.8 ) Pub Date : 2020-05-05 , DOI: 10.1002/poc.4078
Debanjana Ghosh 1 , Shainaz Landge 1 , Lei Zhu 2 , Unodinma Ofulue 1 , Oluwagbotemi A. Akinsoji 1 , Richard D. Govan 1 , Aikohi Ugboya 1 , Vincent Hernandez 1 , Kayley Yates 1 , Arneshia Henderson 1 , Karelle S. Aiken 1
Affiliation  

The influence of strongly electron donating amino groups on a hydroxyaromatic 1,2,3‐triazolyl anion chemosensor was investigated with spectroscopic studies (ultraviolet‐visible [UV‐vis], fluorescence, and nuclear magnetic resonance [NMR]) and computational analyses. This work focused on 2‐, 3‐ and 4‐amino derivatives of the parent molecule, 2‐(4‐phenyl‐1H‐1,2,3‐triazol‐1‐yl)phenol (PTP). The effect on signal‐output, selectivity, sensitivity, and the mechanism of response was explored. In all cases, the incorporation of the amino group enhances fluorescence during anion detection while retaining key properties (the receptor site, a blue‐fluorescent response, and the ability to detect F, H2PO4, and AcO—strongest response to F). Specifically, sensitivity to F is impacted by the amino group's location. The 2‐amino is most responsive to F, more than PTP and the other amino regioisomers. Results from this work are important for developing predictive, structure‐signal tuning models, which will be used in the targeted design of sensors based on the PTP scaffold.

中文翻译:

氨基取代基对羟基芳族1,2,3-三唑基化学传感器对阴离子的信号输出,选择性和敏感性的影响-结构-性质关系研究

通过光谱研究(紫外可见[UV-vis],荧光和核磁共振[NMR])和计算分析研究了强电子给体氨基对羟基芳族1,2,3-三唑基阴离子化学传感器的影响。这项工作的重点是母体分子的2-3-4-氨基衍生物2-(4-对苯甲基-1 H - 1,2,3-叔三氮唑-1-基)苯二酚(PTP)。探索了对信号输出,选择性,灵敏度和响应机制的影响。在所有情况下,氨基增强掺入阴离子检测期间荧光,同时保持键属性(受体位点,蓝色荧光响应,并检测F上的能力-,H 2 PO 4 - ,和ACO - -strongest响应到F )。具体而言,到F灵敏度-由氨基组的位置的影响。该2-氨基是最敏感到F - ,超过PTP和其他氨基区域异构体。这项工作的结果对于开发预测性结构信号调谐模型非常重要,该模型将用于基于PTP支架的传感器的目标设计中。
更新日期:2020-05-05
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