Synthesis of Novel Iono- and Photochromic Spiropyrans Derived from 6,7-Dihydroxy-8-Formyl-4-Methyl-2H-Chromene-2-One

�-hydroxy group were synthesized and their spectral properties as well as abilities for complexation with metal ions studied. In solutions they exist as equilibrium mixture of spirocyclic (A) and merocyanine (B) isomers. The largest content of merocyanine form was found for the derivative with an electron-donating methyl group in position 5 of hetaryl fragment. The irradiation of SPPs in acetonitrile shifts the equilibrium to the B form. Similar effect causes the addition of metal cations due to formation of colored complexes with merocyanine isomers.

[1]  P. G. Sammes,et al.  Photochromic crowned spirobenzopyrans: Quantitative metal-ion chelation by UV, competitive selective ion-extraction and metal-ion transportation demonstration studies , 2008 .

[2]  O. Fedorova,et al.  Spironaphtoxazines produced from crown-containing dihydroisoquinolines: Synthesis and spectroscopic study of cation-dependent photochromism , 2007 .

[3]  V. Minkin,et al.  Photo- and ionochromism of 5’-(4,5-diphenyl-1,3-oxazol-2-yl) substituted spiro[indoline-naphthopyrans] , 2006 .

[4]  L. De Cola,et al.  Synthesis, photophysical, photochemical, and redox properties of nitrospiropyrans substituted with Ru or Os tris(bipyridine) complexes. , 2006, Inorganic chemistry.

[5]  L. Popov,et al.  New binuclear copper(II) complexes with bishydrazones derived from spiropyran of the benzoxazinonium series , 2006 .

[6]  M. Abdel-Mottaleb,et al.  Effect of complexation with lanthanide metal ions on the photochromism of (1,3,3-trimethyl-5′-hydroxy-6′-formyl- indoline-spiro2,2′-[2h]chromene) in different media , 2006 .

[7]  V. Minkin,et al.  Spiropyrans and Spirooxazines. Part 3. Synthesis of Photochromic 5′‐(4,5‐Diphenyl‐1,3‐oxazol‐2‐yl)‐spiro[indoline‐2,3′‐naphtho [2,3‐b]pyran]. , 2006 .

[8]  Feng Liu,et al.  Copper ion-selective fluorescent sensor based on the inner filter effect using a spiropyran derivative. , 2005, Analytical chemistry.

[9]  T. Deligeorgiev,et al.  Effect of complexation on the photochromism of 5'-(benzothiazol-2-yl)spiroindolinonaphthooxazines in polar solvents , 2005 .

[10]  V. Minkin,et al.  Spiropyrans and spirooxazines. 3. Synthesis of photochromic 5′-(4,5-diphenyl-1,3-oxazol-2-yl)-spiro[indoline-2,3′-naphtho[2,3-b]pyran] , 2005 .

[11]  Yunhua Gao,et al.  Photo-switchable molecular devices based on metal-ionic recognition , 2005 .

[12]  V. Minkin,et al.  Photochromic spiro[indoline-pyridobenzopyrans]: fluorescent metal ion sensors , 2004 .

[13]  Deqing Zhang,et al.  Photocontrolled Electron Transfer Reaction between a New Dyad, Tetrathiafulvalene−Photochromic Spiropyran, and Ferric Ion , 2004 .

[14]  R. Kopelman,et al.  Tunable photochromism of spirooxazines via metal coordination. , 2003, Journal of the American Chemical Society.

[15]  B. Lukyanov,et al.  Binuclear Copper(II) Complexes with Hydrazones Containing Spiropyran Fragment , 2003 .

[16]  Olga A. Fedorova,et al.  Photoswitchable molecular receptors , 2003 .

[17]  K. Kimura,et al.  Molecular Design and Applications of Photochromic Crown Compounds — How Can We Manipulate Metal Ions Photochemically? , 2003 .

[18]  K. Kimura,et al.  Molecular Design and Applications of Photochromic Crown Compounds —How Can We Manipulate Metal Ions Photochemically?— , 2003 .

[19]  V. Lokshin,et al.  Spirooxazines: synthesis, structure, spectral and photochromic properties , 2003 .

[20]  K. Kamada,et al.  Decisive Factors in the Photoisomerization Behavior of Crowned Spirobenzopyrans: Metal Ion Interaction with Crown Ether and Phenolate Anion Moieties , 2002 .

[21]  Kamada,et al.  Synthesis and Photochromism of Crowned Spirobenzothiapyran: Facilitated Photoisomerization by Cooperative Complexation of Crown Ether and Thiophenolate Moieties with Metal Ions. , 2000, The Journal of organic chemistry.

[22]  J. Winkler,et al.  Photodynamic Fluorescent Metal Ion Sensors with Parts per Billion Sensitivity , 1998 .

[23]  Mihály T. Beck,et al.  Chemistry of Complex Equilibria , 1970 .

[24]  R. Stephenson.  A and V , 1962, The British journal of ophthalmology.