Journal
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
Volume 95, Issue 10, Pages 1428-1437Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.20220195
Keywords
Supramolecular chemistry; Molecular recognition; Naked-eye-detectable molecular sensor
Categories
Funding
- JSPS KAKENHI [17H06173, 20H02728, 20K05461]
- JSPS [17H05430]
- JST CREST [JPMJCR19R2]
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A molecular sensor has been developed for the naked-eye detection of glutaric acid and isophthalic acid. The sensor selectively forms 1:2 complexes with C3 dicarboxylic acids and dimerizes through strong π-π stacking interactions.
We report a molecular sensor, comprising a porphyrin core and four 2-aminoquinolyl groups at meso positions, for the naked-eye detection of glutaric acid and isophthalic acid, both featuring a C3 spacer between two CO2H groups. In the presence of the C3 dicarboxylic acids, solutions of the porphyrin sensor underwent significant changes in color and absorption spectra. NMR spectroscopy and X-ray crystallography revealed that the porphyrin derivative bound to two molecules of the C3 dicarboxylic acids selectively to form 1:2 complexes, which dimerized through strong p-stacking interactions. Magnetic circular dichroism (MCD) spectroscopy and density functional theory (DFT) calculations suggested that the red-shifting of the Q-bands in the absorption spectra of the porphyrin derivative arose from tilted quinolyl rings in the dimeric complexes. In addition, we found that a test strip containing the porphyrin sensor could also be used to efficiently detect glutaric acid and isophthalic acid.
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