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具有咪唑核心的新型 Y 形荧光染料的合成与表征。

Synthesis and characterization of new Y-shaped fluorophores with an imidazole core.

机构信息

Department of Chemistry, Faculty of Sciences, Dokuz Eylul University, Tinaztepe Campus, 35160, Buca, Izmir, Turkey.

出版信息

J Fluoresc. 2012 Jul;22(4):1159-64. doi: 10.1007/s10895-012-1055-z. Epub 2012 Apr 1.

DOI:10.1007/s10895-012-1055-z
PMID:22466082
Abstract

Four new y-shaped fluorophores of 4- {4,5-[2,2'-Bis(2,4,6-trimethoxyphenyl)vinyl]-1-H-imidazole-2-yl}benzonitrile 1a, 2-phenyl-{4,5-[2,2'-Bis(2,4,6-trimethoxyphenyl)vinyl]-1-H-imidazole} 1b, 2- (9-anthryl)-{4,5-[2,2'-Bis(2,4,6-trimethoxyphenyl)vinyl] }-1-H-imidazole 1c and 2- (4-nitrophenyl) - {4,5-[2,2'-Bis(2,4,6-trimethoxyphenyl)vinyl] -1-H-imidazole 1d which bear an imidazole core, were synthesized for the first time via intermediate 1,6-Bis(2,4,6-trimethoxyphenyl)hexa-1,5-diene-3,4-dion with different aldehydes. The structures of the new derivatives were confirmed by (1)H NMR, (13)C NMR and FT-IR. The optical properties such as absorption and emission maxima, Stokes' shift and quantum yield values were investigated in solvents of toluene, tetrahydrofuran and acetonitrile. The products show intense emission maxima in the range of 440-630 nm. The imidazole derivatives exhibited excellent photostabilities.

摘要

四个新的 Y 型荧光团,4- {4,5-[2,2'-二(2,4,6-三甲氧基苯基)乙烯基]-1-H-咪唑-2-基}苯腈 1a、2-苯基-{4,5-[2,2'-二(2,4,6-三甲氧基苯基)乙烯基]-1-H-咪唑} 1b、2-(9-蒽基)-{4,5-[2,2'-二(2,4,6-三甲氧基苯基)乙烯基]}-1-H-咪唑 1c 和 2-(4-硝基苯基)-{4,5-[2,2'-二(2,4,6-三甲氧基苯基)乙烯基]-1-H-咪唑 1d,这些荧光团都带有一个咪唑核心,是通过中间产物 1,6-双(2,4,6-三甲氧基苯基)己-1,5-二烯-3,4-二酮与不同的醛首次合成的。新衍生物的结构通过(1)H NMR、(13)C NMR 和 FT-IR 得到确认。在甲苯、四氢呋喃和乙腈等溶剂中研究了它们的光学性质,如吸收和发射最大值、Stokes' 位移和量子产率值。产物在 440-630nm 范围内显示出强烈的发射最大值。咪唑衍生物表现出优异的光稳定性。

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