Premium
Turn‐on chemosensors for silver ions based on oligomers with diaza‐16‐crown 6‐ether receptors and aromatic fluorophore end groups
Author(s) -
Yamaguchi Isao,
Shingai Saki
Publication year - 2012
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.3191
Subject(s) - oligomer , pyridinium , chemistry , polymer chemistry , ether , crown ether , oxadiazole , photoinduced electron transfer , fluorophore , diphenyl ether , photochemistry , electron transfer , medicinal chemistry , ion , organic chemistry , fluorescence , physics , quantum mechanics
The reaction of N ‐(2,4‐dinitrophenyl)pyridinium chloride ( 1 ), diaza‐18‐crown 6‐ether (DA18C6) and 2,5‐bis(aminophenyl)‐1,3,4‐oxadiazole ( 2 ) caused the opening of the pyridinium ring and yielded an ionic oligomer (oligomer‐1) comprising a 5‐DA18C6‐penta‐2,4‐dienylideneammonium chloride main chain and 2‐(4‐aminophenyl)‐5‐phenyl‐1,3,4‐oxadiazole or 2‐(4‐ N ‐phenylpyridinium)‐5‐phenyl‐1,3,4‐oxadiazole end groups. Accordingly, the reaction of 1 , DA18C6 and 2,7‐diaminofluorene ( 3 ) yielded oligomer‐2. The structures of oligomer‐1 and oligomer‐2 were determined by comparing their 1 H NMR spectra with those of model compounds, which were synthesized by the 1:1 reaction of 1 with 2 or 3 . Oligomer‐1 and oligomer‐2 exhibited weak bluish‐green photoluminescence (PL) before the inclusion of Ag + in the DA18C6 receptor, after which they exhibited strong bluish‐green PL. These observations can be explained by the occurrence of photoinduced electron transfer in the oligomers. Copyright © 2011 Society of Chemical Industry