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

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

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 Zn 2+ coordinatio...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 50; no. 21; pp. 2573 - 2576
Main Authors: Alhashimy, Nameer, Byrne, Robert, Minkovska, Stela, Diamond, Dermot
Format: Journal Article
Language:English
Published: Elsevier Ltd 27-05-2009
Subjects:
Merocyanine
Photo-switchable sensors
Photochromism
Spirooxazine
Photo-switchable sensors
Photochromism
Merocyanine
Spirooxazine
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Summary: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 Zn 2+ 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 Zn 2+ complex by 20-fold compared to the methylated indole 6.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.03.080