Photochromic 2-(N-acyl-N-arylaminomethylene)benzo[b]thiophene-3(2H)-ones with fluorescent labels and/or crown-ether receptors

被引：15
|
作者：
Dubonosov, AD [1 ]
Minkin, VI [1 ]
Bren, VA [1 ]
Popova, LL [1 ]
Rybalkin, VP [1 ]
Shepelenko, EN [1 ]
Tkalina, NN [1 ]
Tsukanov, AV [1 ]
机构：
[1] Rostov State Univ, Inst Phys & Organ Chem, 194-2 Stachka Av, Rostov Na Donu 344090, Russia
来源：
ARKIVOC | 2003年
关键词：
2-(N-acyl-N-arylaminomethylene)benzo[b]thiophene-3(2H)-ones; photochromism; molecular switches; chemosensors;
D O I：
10.3998/ark.5550190.0004.d03
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Novel N-acylaminovinyl ketones of the benzo[b] thiophene series (AAB) capable of molecular switching of fluorescence or complexation with metal ions have been synthesized and their photochromic behavior studied using UV-Vis absorption/emission and H-1-/Li-7-NMR spectroscopy. Under UV irradiation the AAB compounds 2a-c containing fluorescent labels as their N-aryl substituents undergo Z/E-photo-isomerization and N-->O acyl rearrangement resulting in the formation of O-acyl isomers 3a-c. The photo-switching of fluorescence has been found in the 4-fluorenonyl derivative 2a. The benzo-15-crown-5-containing AAB 2d, e are also susceptible to the same type of photo-initiated rearrangement. The corresponding O-acyl isomers 3d-e represent a group of chemosensors which readily form stable complexes with alkali- and alkali-earth-metal cations. The AAB 2d exhibits specific selectivity for Li+ ion in the presence of Na+, K+ and Cs+.
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页码：12 / 20
页数：9
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