Spiropyrans: Synthesis, Properties, and Application. (Review)

Abstract

Published data on the synthesis and structural modification of spiropyrans and bisspiropyrans and production of the heteroanalogs of spiropyrans are classified and analyzed. The chemical characteristics of spiropyrans, including complexation of the open-chain isomers and cyclic forms are examined. Special attention is paid to the photochromic characteristics of spiropyrans at interfaces between phases.

Control of optical properties through photochromism: a promising approach to photonics

“…In the literature, many compounds belonging to different families (diarylethenes [1,4,5,[11][12][13][14], spiro compounds [15][16][17][18], fulgides [19]) have been synthesized and characterized and those reported in the table represent just examples. The first set of diarylethenes (1)(2)(3)(4)(5) shows the effect of the presence of electroactive substituents on the absorption maxima of the colored form.…”

Synthesis, crystal structures, and laser flash photolysis of 3-nitro-7a,15-methanonaphtho[1',2':6,7][1,3]oxazepino[3,2-a]indole derivatives

“…9,10 The synthesis of 1′,3′-dihydrospiro-[chromene-2,2′-indoles] is usually based on the condensation of 2-methylideneindoline derivatives with such aryl aldehydes as 5-nitrosalicylaldehyde. 1,11 Similar reactions of the aforementioned indolines with various 2-hydroxynaphthaldehydes afforded spiro[benzo[f]-chromene-3,2′-indoles], which, like spiro[chromene-2,2′-indoles], change colour when subjected to such external stimulus as UV-irradiation or treatment with active nucleophiles. [12][13][14] In our previous work, we showed that the condensation of 1-substituted imidazo [ 15,16 The latter compounds were used in the preparation of imprinted polymer stationary phases.…”

Photochromic and thermochromic spiranes 33. Synthesis of a new indolinonaphthoxazino- bisspiropyran and investigation of its photochromic characteristics

“…Thus, the geometric structure of the C spiro -node and the benzopyran fragment in the investigated compounds is similar to the structure of the previously investigated indoline and benzoxazine spiropyrans. In compound 3, as also in compound 2, the inclusion of the carbonyl group C(4)=O (2) in the benzoxazine fragment leads to a substantial change in the electronic and geometric picture of the structure of the N-node. The projection of the N(3) atom from the corresponding plane of the coordinating atoms C(2'2), C(4), and C (3) …”

“…The possible strong bathochromic shift of the maximum of the doubly opened bisspiropyran makes it possible to use them for the creation of data carriers that can be overwritten by suitable mid-IR radiation [5]. On the basis of 8'-formyl 7'-hydroxy-3-methyl-4-oxospiro (2,3-dihydronaphtho[2,1-e] [1,3]oxazine-2,2'-[3H]-chromene) (2) we obtained the new unsymmetrical bisspiropyran 3 [6]. For final determination of the structure of the obtained bisspiropyran the data from X-ray crystallographic analysis were used (Fig.…”