以具有激发态分子内质子转移荧光的水杨醛亚胺衍生物N-(对二甲氨基苯基)水杨醛亚胺(1)为阴离子识别受体,研究了乙腈中受体1荧光对多种阴离子的响应,发现1对氟离子表现出高的响应选择性.乙腈中1的质子转移荧光位于545nm.加入氟离子后.于479nm处出现1的阴离子荧光.氟离子经由布朗斯特酸碱作用影响受体1的激发态质子转移荧光,实现了双重荧光比率法对氟离子的高选择性识别响应.
A fluorescent anion receptor, N-(p-dimethylaminophenyl)salicylaldimine(1), was designed and synthesized. 1 was shown to undergo the excited-state intramolecular proton transfer(ESIPT) upon excitation. In acetonitrile,the response of 1 toward various anions such as F^- , H2 PO4^- , CH3 COO^- , HSO4^- , Cl^- , etc. was investigated via its absorption and fluorescence spectra. 1 was highly selective response to fluoride anion. The ESIPT fluorescenee of 1 locates at 545 nm. Anion fluorescence of 1 was appeared at 479 nm when introduction of F- to I solution. This ESIPT process of I was found inhibited only by fluoride anion via a deprotonation process. The deprontonation process mechanism of I interaction with fluoride anion was proved by ^1H-NMR spectra. The inhibition of ESIPT consequently resulted in a ratiometric response in the fluorescence of 1 toward fluoride anion whereas other anions showed practically no influence on the fluorescence of 1.