Synthesis of some new fluorescentindicators and spectroscopic applications

In this study, oxazol-5-one class fluorescent molecules which are the cyclic anhydrides of N-acyl aminoacids and are formed of five membered heterocycle systems have been synthesized, purified, photophysically investigated and their sensor applications were performed. Three different classes of azlactones which have N-phenyl-aza-15-crown-5, antracene and carbazole groups have been synthesized. As azlactone derivatives which have N-phenyl-aza-15-crown-5 group, 2-phenyl-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]oxazol-5-one (CPO-1), 2-(3,5-dinitrophenyl)-4-[4-(1,4,7,10-tetraoxa-13-azascyclopentadecyl)benzylidene]oxazol-5-one (CPO-2), 2, 2-(p-nitrophenyl)-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]oxazol-5-one (CPO-3) and 2-(p-tolyl)-4-[4-(1,4,7,10-tetraoxa-13-azascyclopentadecyl)benzylidene]oxazol-5-one (CPO-4) molecules were synthesized. As fluorescent molecules which contain antracene structure, 2-phenyl-4-antralidene-5-oxazolone (ANT-I), 2-(4-tolyl)-4-antralidene-5-oxazolone (ANT-II) and 2-(4-nitrophenyl)-4-antralidene-5-oxazolone (ANT-III) were synthesized. As azlactone which contains carbazole group, 4-[(9-buthyl-6-{[2-(3,5-dinitrophenyl)-5-oxo-1,3-oxazol-4(5H)-lydene]methyl}-9H-carbazol-3-yl)methylene]-2-(3,5-dinitrophenyl)-1,3-oxazol-5(4H)-one was synthesized. Synthesized oxazol-5-one derivatives were purified by column chromatography and recrystallzation, and their structures were confirmed by FT-IR, 1H-NMR ve 13C-NMR spektroscopic tecniques. The photophysical properties of the derivatives synthesized were investigated by UV-vis absorption and emission spectroscopy. By immobilizing, CPO derivatives in optically transparent polyvinyl chloride matrix, sensor systems for detection of acetylcholinechloride, donepezil and glucose were developed. Also, the response of the same derivatives to Ca2+, Ba2+, K+, NH4+ and Na+ cations which have biological importance have been investigated.