A novel phosphate chemosensor utilizing anion-induced fluorescence change.
[structure: see text] The neutral receptor N,N'-bis[3,5-di[(1-pyrenylmethyl)carbamoyl]benzyl] pyridine-2,6-dicarbamide (2) provides a pseudo-tetrahedron cleft and multiple hydrogen bondings to form a 1:1 complex with phosphate ion in a highly selective manner, by comparison with other anions (F(-), Cl(-), Br(-), SCN(-), AcO(-), NO(3)(-), ClO(4)(-), and HSO(4)(-)). The binding strength can be inferred from the emission intensity ratio of the pyrene monomer (lambda(max) 377 nm) to the excimer (lambda(max) 477 nm). Fluorescence titration, X-ray analysis, and NMR studies support a proposed complexation model.
Liao
Jen-Hai
JH
Department of Chemistry, National Taiwan University, Taipei, Taiwan 106, Republic of China.
Chen
Chao-Tsen
CT
Fang
Jim-Min
JM
D018360:Crystallography, X-Ray; D005453:Fluorescence; D005456:Fluorescent Dyes; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010710:Phosphates / Q000737:chemistry*; D011721:Pyrenes / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
D005456:Fluorescent Dyes; D007202:Indicators and Reagents; C451484:N,N'-bis(3,5-di-((1-pyrenylmethyl)carbamoyl)benzyl)pyridine-2,6-dicarbamide; D010710:Phosphates; D011721:Pyrenes; D011725:Pyridines