Department of Chemistry , The University of Texas at Austin , 105 East 24th Street, Stop A5300 , Austin , Texas 78712-1224 , United States.
Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center , East China University of Science & Technology , Shanghai 200237 , P. R. China.
J Am Chem Soc. 2019 Sep 18;141(37):14798-14806. doi: 10.1021/jacs.9b07170. Epub 2019 Sep 4.
We report here the fluorescent sensing of both aromatic and linear saturated dicarboxylate anions () (as their tetrabutylammonium salts) with different lengths and shapes in acetonitrile using a single fluorescent probe, i.e., the bis-calix[4]pyrrole-appended 9,14-diphenyl-9,14-dihydrodibenzo[,]phenazine () incorporating a vibration-induced emission (VIE) phenazine core. Fluorescence titration studies revealed that treating with dicarboxylate guests capable of forming pseudomacrocyclic host-guest complexes via multiple hydrogen-bonding interactions between the dicarboxylates and calix[4]pyrrole moieties led to a blue-shift in the emission of the phenazine core. The binding-based fluorescence-tuning features of allow the underlying binding events and inferred structural changes to be monitored in the form of different chromaticity outputs. The analyte-induced differences in the fluorescence response to cover a wide range within the chromaticity diagram and can be visualized readily. The present system thus functions as a rudimentary dicarboxylate anion sensor. It highlights the potential benefits associated with combining a tunable VIE core with noncovalent binding interactions and thus sets the stage for the development of new fluorescent chemosensors where a single chemical entity responds to different analytes with a high level of tunability.
我们在这里报告了使用单个荧光探针，即双杯[4]吡咯修饰的 9,14-二苯基-9,14-二氢二苯并[,]吩嗪（），在乙腈中对不同长度和形状的芳香族和线性饱和二羧酸阴离子（）（作为它们的四丁基铵盐）的荧光传感。荧光滴定研究表明，用二羧酸客体处理 ，这些客体可以通过二羧酸和杯[4]吡咯部分之间的多个氢键相互作用形成拟大环主体-客体配合物，导致吩嗪核心的发射发生蓝移。基于结合的荧光调谐特性允许以不同色度输出的形式监测潜在的结合事件和推断的结构变化。分析物对 荧光响应的差异在色度图中覆盖了很宽的范围，可以很容易地可视化。因此，本系统可作为一种基本的二羧酸阴离子传感器。它突出了将可调谐 VIE 核心与非共价键合相互作用相结合所带来的潜在好处，并为开发新的荧光化学传感器奠定了基础，其中单个化学实体可以对不同的分析物进行高度可调的响应。
