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Hexaamide Molecule Annexed with Pyrenes for Selective Detection of Phosphate and Pyrophosphate Ions by Ratiometric Fluorescence Changes
Author(s) -
Liao JenHai,
Chen ChaoTsen,
Fang JimMin
Publication year - 2006
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200600190
Subject(s) - chemistry , pyrophosphate , fluorescence , pyrene , ion , phosphate , molecule , excimer , monomer , inorganic chemistry , photochemistry , organic chemistry , enzyme , physics , quantum mechanics , polymer
N , N ′‐bis{3,5‐di[(1‐pyrenylmethyl)carbamoyl]benzyl}pyridine‐2,6‐dicarbamide (compound 1 ) provides a pseudo‐tetrahedron cleft and multiple hydrogen bondings to form a 1:1 complex with phosphate (or pyrophosphate) ion in a highly selective manner, in comparison with other anions (F − , Cl − , Br − , SCN − , AcO − , NO 3 − , and ClO 4 − ). Compound 1 bears four pyrene rings as the sensitive fluorescent readout unit for phosphate and pyrophosphate ions. The binding strength can be inferred from the emission intensity ratio of the pyrene monomer (λ max = 377 nm) to the excimer (λ max ˜ 480 nm). The enhanced multiple hydrogen bondings and ratiometric sensing mechanism render an opportunity for sensing pyrophosphate ion at micromolar concentration, even in water‐containing solution. The binding model is supported by fluorescence and 1 H NMR studies.