TY - JOUR
T1 - Phenanthroline-derived ratiometric chemosensor for ureas
AU - Engel, Yoni
AU - Dahan, Adi
AU - Rozenshine-Kemelmakher, Emily
AU - Gozin, Michael
PY - 2007/3/30
Y1 - 2007/3/30
N2 - The syntheses of 1,10-phenanthroline fluorophore-based chemosensor 7 and its truncated analog 9 are reported. Interactions of these compounds with urea, thiourea, 1,3-dimethylurea, tetrahydropyrimidin-2(lH)-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 to be capable of distinguishing between neutral ureas and their salts, by producing a different optical response for each type of compounds. The complexation of urea by 7 was also studied by selective-NOE 1H NMR, 13C NMR (using 13C- labeled guest), and MALDI-TOF mass spectrometry. In addition, we performed DFT calculations (B3LYP 3-21g** level) for structures of complexes of 7 with urea, imidazolidin-2-one, and tetrahydropyrimidin-2(lH)-one. Development of chemosensor 7-type compounds in conjunction with differential excitation-emission spectroscopy represents an important step toward the development of novel tools for ureas and their salts analysis.
AB - The syntheses of 1,10-phenanthroline fluorophore-based chemosensor 7 and its truncated analog 9 are reported. Interactions of these compounds with urea, thiourea, 1,3-dimethylurea, tetrahydropyrimidin-2(lH)-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 to be capable of distinguishing between neutral ureas and their salts, by producing a different optical response for each type of compounds. The complexation of urea by 7 was also studied by selective-NOE 1H NMR, 13C NMR (using 13C- labeled guest), and MALDI-TOF mass spectrometry. In addition, we performed DFT calculations (B3LYP 3-21g** level) for structures of complexes of 7 with urea, imidazolidin-2-one, and tetrahydropyrimidin-2(lH)-one. Development of chemosensor 7-type compounds in conjunction with differential excitation-emission spectroscopy represents an important step toward the development of novel tools for ureas and their salts analysis.
UR - http://www.scopus.com/inward/record.url?scp=34047237040&partnerID=8YFLogxK
U2 - 10.1021/jo062130h
DO - 10.1021/jo062130h
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AN - SCOPUS:34047237040
SN - 0022-3263
VL - 72
SP - 2318
EP - 2328
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 7
ER -