Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 37, Pages 14798-14806Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b07170
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Funding
- Office of Basic Energy Sciences, U.S. Department of Energy (DOE) [DE-FG02-01ER15186]
- Robert A. Welch Foundation [F-0018]
- NSFC/China [21788102]
- Shanghai Municipal Science and Technology Major Project [2018SHZDZX03]
- China Scholarship Council (CSC)
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We report here the fluorescent sensing of both aromatic and linear saturated dicarboxylate anions (DC2-) (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[a,c]phenazine (DPAC-bisC4P) incorporating a vibration-induced emission (VIE) phenazine core. Fluorescence titration studies revealed that treating DPAC-bisC4P 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 DPAC-bisC4P 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 DC2- 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.
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