Phenanthroline-derived ratiometric chemosensor for ureas

Yoni Engel, Adi Dahan, Emily Rozenshine-Kemelmakher, Michael Gozin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)2318-2328
Number of pages11
JournalJournal of Organic Chemistry
Volume72
Issue number7
DOIs
StatePublished - 30 Mar 2007

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