Novel synthesis and characterisation of 3,3-dimethyl-5′-(2-benzothiazolyl)-spironaphth(indoline-2,3′-[3H]naphth[2,1-b] [1,4]oxazine) derivatives

被引：18

作者：

Alhashimy, Nameer ^{[1
]}

Byrne, Robert ^{[1
]}

Minkovska, Stela ^{[1
,2
]}

Diamond, Dermot ^{[1
]}

机构：

[1] Dublin City Univ, Sch Chem Sci, Natl Ctr Sensor Res, Adapt Sensors Grp, Dublin 9, Ireland

[2] Bulgarian Acad Sci, Inst Catalysis, Sofia 111, Bulgaria

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 21期

基金：

爱尔兰科学基金会;

关键词：

Spirooxazine; Merocyanine; Photo-switchable sensors; Photochromism; PHOTOCHROMISM; SPIROPYRAN; COMPLEXATION; CHELATION; MEROCYANINES; SURFACE;

D O I：

10.1016/j.tetlet.2009.03.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel modified spirooxazines (SOs) with additional chelating groups were synthesised and the crystal structure of one of these was determined. UV-vis spectroscopic characterization of the photoisomerization of the SO derivatives shows that the photochromic behaviour is altered with Zn2+ coordination. In particular, addition of a group as in carboxylic acid 5 to the indole section of the SO increases the lifetime of the merocyanine Zn2+ complex by 20-fold compared to the methylated indole 6. (C) 2009 Published by Elsevier Ltd.

引用

页码：2573 / 2576

页数：4

共 50 条

[21] REVERSIBLE FORMATION AND ERADICATION OF COLORS BY IRRADIATION AT LOW TEMPERATURES - A PHOTOCHEMICAL MEMORY MODEL [J].

HIRSHBERG, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (10) :2304-2312

[22] Diarylethenes for memories and switches [J].

Irie, M .

CHEMICAL REVIEWS, 2000, 100 (05) :1685-1716

[23] Effect of complexation on the photochromism of 5′-(benzothiazol-2-yl)spiroindolinonaphthooxazines in polar solvents [J].

Jeliazkova, BG ;

Minkovska, S ;

Deligeorgiev, T .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2005, 171 (02) :153-160

[24] Three-dimensional optical data storage using photochromic materials [J].

Kawata, S ;

Kawata, Y .

CHEMICAL REVIEWS, 2000, 100 (05) :1777-1788

[25] Synthesis, characterization and photochromic studies of spirooxazine-containing 2,2'-bipyridine ligands and their rhenium(I) tricarbonyl complexes [J].

Ko, CC ;

Wu, LX ;

Wong, KMC ;

Zhu, NY ;

Yam, VWW .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (03) :766-776

[26]

LEBACCON M, 1979, J CHEM RES-S, P154

[27] SUPRAMOLECULAR CHEMISTRY - SCOPE AND PERSPECTIVES MOLECULES, SUPERMOLECULES, AND MOLECULAR DEVICES [J].

LEHN, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1988, 27 (01) :89-112

[28] CHROMOIONOPHORES AND FLUOROIONOPHORES - A NEW CLASS OF DYE REAGENTS [J].

LOHR, HG ;

VOGTLE, F .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (03) :65-72

[29]

Lokshin V.A., 2002, RUSS CHEM REV+, V71, P893, DOI DOI 10.1070/RC2002V071N11ABEH000763

[30]

Maeda S, 1999, T APPL CHEM, V1, P85

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