Abstract
| - The syntheses of 1,10-phenanthroline fluorophore-based chemosensor 7 and its truncated analog 9 arereported. Interactions of these compounds with urea, thiourea, 1,3-dimethylurea, tetrahydropyrimidin-2(1H)-one, imidazolidin-2-one, and selected uronium salts were assessed by three-dimensional excitation−emission spectroscopy, UV−vis absorbance, and fluorescence titrations. Chemosensor 7 was found tobe capable of distinguishing between neutral ureas and their salts, by producing a different optical responsefor each type of compounds. The complexation of urea by 7 was also studied by selective-NOE 1HNMR, 13C NMR (using 13C-labeled guest), and MALDI-TOF mass spectrometry. In addition, we performedDFT calculations (B3LYP 3-21g** level) for structures of complexes of 7 with urea, imidazolidin-2-one, and tetrahydropyrimidin-2(1H)-one. Development of chemosensor 7-type compounds in conjunctionwith differential excitation−emission spectroscopy represents an important step toward the developmentof novel tools for ureas and their salts analysis.
|