Useful spectrokinetic methods for the investigation of photochromic and thermo-photochromic spiropyrans

Molecules

Volumn 13, Issue 9, 2008, Pages 2260-2302

  Maafi, Mounir ^a  

^a DE MONTFORT UNIVERSITY   (United Kingdom)

Author keywords

Kinetic elucidation; Photochromic and thermochromic compounds; Spectrokinetic methods; Spiropyrans

Indexed keywords

BENZOPYRAN DERIVATIVE; INDOLE DERIVATIVE; NITRO DERIVATIVE; SPIROPYRAN;

ALGORITHM; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; METHODOLOGY; REVIEW; SPECTROPHOTOMETRY; THERMODYNAMICS;

ALGORITHMS; BENZOPYRANS; INDOLES; KINETICS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NITRO COMPOUNDS; SPECTROPHOTOMETRY; THERMODYNAMICS;

EID: 53249154940     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13092260     Document Type: Review

References (100)

1. Bouas-Laurent, H.; Dürr, H. Organic photochromism (IUPAC Technical Report). Pure Appl. Chem. 2001, 73, 639-665.
2. Brown G. H. Photochromism: molecules and systems, Dürr H.; Bouas-Laurent H., Eds.; Elsevier: Amsterdam, 2003.
3. Bertelson, RC. Topics in Applied Chemistry "Organic Photochromic and Thermochromic Compounds". Crano, J.C., Guglielmetti, R.J., Eds; Plenum Press: New York, USA, 1999. Volumes 1 and 2.
4. Feringa B.L., Ed. Molecular Switches. Wiley-VCH Verlag: Berlin, Germany, 2001.
5. Irie, M. Diaryethenes for memories and switches. Chem. Rev. 2000, 100, 1685-1716.
6. Minkin, V. I. Photo-, thermo-, solvo-, and electrochromic spiroheterocyclic compounds. Chem. Rev. C 2004, 104, 2751-2776.
7. H.J. Kuhn, S.E. Braslavsky, Chemical actinometry (IUPAC Technical Report). Pure Appl. Chem. 2004, 76, 2105-2146.
8. Fischer, E. The calculation of photostationary state in systems A ⇔ B when only A is known. J. Phys. Chem. 1967, 71, 3704-3706.
9. Flanney Jr. J.B. The photo- and thermochromic transients from substituted 1 ′, 3′, 3′-trimethyl-indolinobenzospiropyrans. J. Am. Chem. Soci. 1968, 90, 5660-5671.
10. Blanc, J.; Ross D.L. A procedure for determining the absorption spectra of mixed photochromic isomers not requiring their separation. J. Phys. Chem. 1968, 72, 2817-2824.
11. Tomlinson, W.J.; Chandross, E.A.; Fork, R.L.; Pryde, C.A.; Lamola, A.A. Reversible Photodimerization: a New Type of Photochromism. Appl. Optics 1972, 11, 533-548.
12. Wyman, G. M.; Zarnegar, B.M.; Excited state chemistry of indigo dyes. Fluoescence vs. cis-trans isomerization. J. Phys. Chem. 1973, 77, 831-837.
13. Wyman G. M. A new method for calculating the absorption spectra of the components of photochromic systems A ⇔ B. Mol. Photochem. 1974, 6, 81-90.
14. P. Appriou, R. Gugglielmetti, F. Garnier, Étude du processus photochimique impliqué dans la réaction d'ouverture du cycle benzopyrannique. J. Photochem. 1978, 8, 145-165.
15. Chu, N.Y.C. Photochromism of spiroindolinonaphthoxazine. 1. Photopysical properties. Can. J. Chem. 1983, 61, 300-305.
16. Brauer, H.-D.; Schmidt, R. A new reusable chemical actinometer for UV irradiation in the 248-334 nm range. Photochem. Photobiol. 1983, 37, 587-591.
17. Brauer, H.-D.; Schmidt, R.; Gauglitz, G.; Hubig, S. Chemical actinometry in the visible (475-610 nm) by meso-diphenylhelianthrene. Photochem. Photobiol. 1983, 37, 595-598.
18. Rau, H.; Greiner, G. Determination of quantum yields of the X/Y isomerization system from spectroscopic data. Europ. Photochem. Assoc. Newsl. 1991, 41, 40-55.
19. Hanazawa, M.; Sumiya, R.; Horikawa, Y.; Irie, M. Thermally irreversible photochromic systems. Reversible photocyclization of 1,2-bis (2-methylbenzo[b]thiophen-3-yl)perfluorocyclocoalkene derivatives. J. Chem. Soc. Chem. Commun. 1992, 206-207.
20. Sheah, J.R.; Diamond, J.J. Measurement of quantum yields for photochemical systems interconverted by light and heat. J. Phys. Chem. 1992, 96, 4938-4944.
21. Gauglitz, G., Scheerer, E. Method for the determination of absorption coefficients, reaction rate constants and thermodynamic data in the system A ⇔ B. J. Photochem. Photobiol. A: Chem. 1993, 71, 205-212.
22. Favaro, G., Malatesta, V.; Mazzucato, U.; Ottavi, G.; Romani, A. Thermally reversible photoconversion of spiroindoline-naphtho-oxazines to photomerocyanines: a photochemical and kinetic study. J. Photochem. Photobiol. A: Chem. 1995, 87, 235-241.
23. Gauglitz, G.; Stoßel, P.; Meier, H.; Rau, H. Photokinetic examination of (Z,E,E)-4,4′-distyrylazobenzene. J. Photochem. Photobiol. A: Chem. 1995, 85, 207-211.
24. Gade, R.; Porada, Th. Determination of quantum yields and product spectra by studying reversible photoisomerization in solution J. Photochem. Photobiol. A: Chem. 1997, 107, 27-34.
25. V. Pimienta, C. Froute, M.H. Deniel, D. Lavabre, R. Guglielmetti, J.C. Micheau . Kinetic modelling of the photochromism and photodegradation of a spiro[indoline-naphthoxazine]. J. Photochem. Photobiol. A: Chem. 1999, 122, 199-204.
26. Yamashita, T. Quantitative Kinetic Analysis of Photochromic Reactions. J. Photopolym. Sci. Technol. 1999, 12, 257-262.
27. Strashnikova, N.; Papper, V.; Parkhomyuk, P.; Likhtenshtein, G. I.; Ratner, V.; Marks, R. Local medium effects in the photochemical behavior of substituted stilbenes immobilized on quartz surfaces. J. Photochem. Photobiol. A: Chem. 1999, 122, 133-142.
28. Matsuda, K.; Irie, M. Photochromism of diarylethenes having nitronyl nitroxides. Tetrahedron Lett. 2000, 41, 2577-2580.
29. Häupl, T.; Zimmermann, T.; Hermann, R.; Brede, O. On the Photochromism of Spiro[cyclohexadiene-dihydroacridines]. Photochem. Photobiol. 2000, 71, 294-299.
30. Brookman. J.; Chacon, J.N.; Sinclair, R.S. Some photophysical studies of cis- and trans-urocanic acid. Photochem. Photobiol. Sci. 2002, 1, 327-332.
31. Tonne, J.; Prinzbach, H.; Michl, J. Double actinometry for rigorous evaluation of quantum yields of clean photoreversible photochemical reactions. Photochem. Photobiol. Sci. 2002, 1, 105-110.
32. Atabekyan, L.S.; Zakharova, G.V.; Ogienko, V.N.; Chibisov, A.K. Photochromic transformations of spiro compounds. 2. The kinetics of photocoloration under continuous irradiation. High Energ. Chem. 2002, 36, 322-325.
33. Sheepwash, M.A.L.; Ward, T.R.; Wang, Y.; Bandyopadhyay, S.; Mitchell, R.H.; Bohne, C. Mechanistic studies on the photochromism of [e]-annelated dimethyldihydropyrenes. Photochem. Photobiol. Sci. 2003, 2, 104-112.
34. Sun, F.; Zhang, F.; Zhao, F.; Zhou, X.; Pu, S. Preparation and photochromic properties of diarylethene nanoparticles. Chem. Phys. Lett. 2003, 380, 206-212.
35. K.D. Belfield, M.V. Bondar, Y. Liu, O.V. Przhonska, A new blue light-emitting oligofluorene glass: synthesis, characterization and photophysical properties. J. Phys. Org. Chem. 2003, 16, 69-78.
36. Airinei, A. ; Barboiu, V.; Rusu, E. ; Timpu D. Photolysis of 4-azidodiphenyl in solution studied by UV absorption spectroscopy. J. Photochem. Photobiol. A: Chem. 2004, 162, 579-584.
37. Zelentsov, S. V.; Simdyanov, I. V. Simulation of exposure of light-sensitive layers: Processes involving reversible reactions. High Energ. Chem. 2005, 39, 179-183.
38. Borisenko, V.; Woolley, G. A. Reversibility of conformational switching in light-sensitive peptides. J. Photochem. Photobiol. A: Chem. 2005, 173, 21-28.
39. Jeong, Y.-C.; Yang, S.I.; Kim, E.; Ahn, K.-K. Development of highly fluorescent photochromic material with high fatigue resistance. Tetrahedron 2006, 62, 5855-5861.
40. Pu, S.; Yang, T.; Li, G.; Xu, J. ; Chen, B. Syntheses and properties of new photochromic diarylethene derivatives having a pyrazole unit. Tetrahedron Lett. 2006, 47, 3167-3171.
41. Attia, M.S.; Khalil, M.M.H.; Abdel-Mottaleb, M.S.A.; Lukyanova, M. B.; Alekseenko, Y.A.; Lukyanov, B. 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. Int. J. Photoenergy 2006, 1-9.
42. Corredor, C.C.; Belfield, K.D.; Bondar, M.V.; Przhonska, O.V.; Hernandez, F.E.; Kachkovsky, O.D. One- and two-photon photochemical stability of linear and branched fluorene derivatives. J. Photochem. Photobiol. A: Chem. 2006, 184, 177-183.
43. Bossi, M.L.; Rodriguez, J.B. ; Aramendia, P.F. Photoinduced changes of absorption and circular dichroism in a chiral nematic phase containing a photochromic fulgide. J. Photochem. Photobiol. A: Chem. 2006, 179, 35-41.
44. Andrey, Kh.V.; Menshykau, D. Kinetics of photochemical reactions in optically dense media with reagent diffusion. J. Photochem. Photobiol. A: Chem (in press).
45. H. Mauser and G. Gauglitz. Photokinetics: Theoretical Fundamentals and Applications. In Comprehensive Chemical Kinetics; Compton R.G.; Hancock G., Eds; Elsevier: Amsterdam, 1998; Volume 36.
46. Görner, H. Photochromism of nitrospiropyrans: effects of structure, solvent and temperature, Phys. Chem. 2001, 3, 416-423.
47. Atabekyan, L.S.; Zakharova, G.V.; Chibisov, A.K. Photochromic transformations of spiro compounds: 1. A new approach to determining the photocoloration quantum yield. High Energ. Chem. 2001, 35, 349-388.
48. Kießwetter, R.; Pustet, N.; Brandl, F.; Mannschreck, A. 1′,3′,3′-Trimethyl-6-nitrospiro[2H-1 benzopyran-2,2′-indoline]: its thermal enantiomerization and the equilibration with its merocyanine. Tatrahedron Asymmetr. 1999, 10, 4677-4687.
49. Bletz, M.; Pfeifer-Fukumura, U.; Kolb, U.; Baumann, W. Ground- and first-excited-singlet-state electric dipole moments of some photochromic spirobenzopyrans in their spiropyran and merocyanine forms. J. Phys. Chem. 2002, 106, 2232-2236.
50. Zhang, J.S.; King, J.; Harris, C. Ultrafast studies of photochromic spiropyrans in solution. J. Am. Chem. Soc. 1992, 114, 10921-10927.
51. Sheng, G.; Leszczynski, J.; Garcia, A.A. ; Rosario, R.; Gust, D; Springer, J. Comprehensive Theoretical Study of the Conversion Reactions of Spiropyrans: Substituent and Solvent Effects. J. Phys. Chem. B 2004, 108, 16233-16243.
52. Cottone, G.; Noto, R.; La Manna, G. Theoretical study of spiropyran-merocyanine thermal isomerization. Chem. Phys. Lett. 2004, 388, 218-222.
53. Hobley, J.; Pfeifer-Fukumura, U.; Bletz, M.; Asahi, T.; Masuhara, H.; Fukumura, H. Ultrafast Photo-Dynamics of a Reversible Photochromic Spiropyran. J. Phys. Chem. 2002, 106, 2265-2270.
54. Wohl, C. J.; Kuciauskas, D. Excited-state dynamics of spiropyran-derived merocyanine isomers. J. Phys. Chem. B 2005, 109, 22186-22191.
55. Celani, P.; Bernardi, F.; Olivucci, M.; Robb, M. A. Conical Intersection Mechanism for Photochemical Ring Opening in Benzospiropyran Compounds. J. Am. Chem. Soc. 1997, 119, 10815-10820.
56. Hunt, P. A.; Robb, M. A. Systematic Control of Photochemistry: The Dynamics of photoisomerization of a model cyanine dye. J. Am. Chem. Soc. 2005, 127, 5720-5726.
57. Sheepwash, M.A.L.; Mitchell, R.H.; Bohne, C. Mechanistic insights into the photochromism of trans-10,10c-methyl-10b,10c-dihydropyrene derivatives. J. Am. Chem. Soc. 2002, 124, 4693-4700.
58. Xie, N.; Chen, Y.; Yao, B.; Lie. M. Photochromic diarylethene for reversible holographic recording. Mat. Sci. Eng. B 2007, 138, 210-213.
59. Biedermann, P.U.; Stezowski, J.J.; Agranat, I. Polymorphism versus thermochromism: interrelation of color and conformation in overcrowded bistricyclic aromatic enes. Chem.: A Europ. J. 2006, 12, 3345-3354.
60. Kaneda, K.; Arai, T. Mechanistic approach to the cyclization reaction of a 2′-hydroxychalcone analogue with light and solvent. Org. Biomol. Chem. 2003, 1, 2041-2043.
61. Gomes, R.; Parola, J.; Laia, C.A.T.; Pina, F. Efficient photochromism from the network of chemical reactions of 7,4′-dihydroxyflavylium in CTAB micelles. Photochem. Photobiol. Sci. 2007, 6, 1003-1009.
62. Ballardini, R.; Ceroni, P.; Credi, A.; Gandolfi, M.T.; Maestri, M.; Semararo, M.; Venturi, M.; Balzani, V. Molecular photochemionics. Adv. Funct. Mat. 2007, 17, 740-750.
63. Wang, P.Y.; Wu, C.J. Photochromic behaviour of some phenoxyanthraquinone dyes in solution and on polyester substrate. Dyes Pigm. 1997, 35, 279-288.
64. Fu, Z.-S.; Sun, B.-B.; Chen, J.; Yuan, L. Preparation and photochromism of carboxymethyl chitin derivatives containing spirooxazine moiety. Dyes Pigm. 2008, 76, 515-518.
65. Vicaro, J.; Katsonis, N.; Ramon, B.S.; Bastiaansen, C.W.M.; Broer, D.J.; Feringa, B.L. Nanomotor rotates microscale objects. Nature 2006, 440, 163.
66. Zhao, L.; Hou, Q.; Sui, D.; Wang, Y.; Jiang, S. Multistate/ multifunctional switches based on photochromic Schiff base. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2007, 67, 1120-1125.
67. Bayrakçeken, F.; Sevinç, P.C. Photophysical properties and photochemical rearrangement of single crystal salicylideneaniline in solution. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2007, 66, 184-187.
68. Tomasuloa, M.; Sortino, S.; Raymo, F.M. A new family of photochromic compounds based on the photoinduced opening and thermal closing of [1,3]oxazine rings. J. Photochem. Photobiol. A: Chem (in press).
69. Asiri, A.M.; Ismaiel, N.H. Novel photochromic system derived from tetracyanoquinodimethane and pyrazoles. Pigm. Resin Technol. 2006, 35, 147-150.
70. Tatewaki, H.; Baden, N.; Momotake, A.; Arai, T.; Terazima, M. Dynamics of Water-Soluble Stilbene Dendrimers upon Photoisomerization. J. Phys. Chem. B 2004, 108, 12783-12789.
71. Knoll, H. Effects of unidirectional and mutual interactions between microstructures and azo dyes as kinetic probe molecules on cis → trans isomerization rate constants in aqueous P85 and F88 triblock copolymer solutions. Int. J. Chem. Kinet. 2008, 40, 59-65.
72. Maafi, M.; Aaron, J.J.; Lion, C., Direct valence isomerization of newly synthesized norbornadiene aromatic derivatives. A kinetic and photophysical study. Chem. Lett. 1994, 1865-1868.
73. Maafi, M.; Aaron, J.J.; Lion, C., Synthesis, photophysical properties and valence photoisomerization of new fluorescent aromatic norbornadienes. New J. Chem. 1996, 20, 559-570.
74. Maafi, M.; Aaron, J.J.; Lion, C., Electrosynthesis and photoisomerization of a new fluorescent aromatic polymer bearing a pendant substituted norbornadiene group. Synthet. Metal 1996, 167-169.
75. D'Aniello, C.; Musto, P.; Venditto, V.; Guerra, G. Photoisomerization patterns based on molecular complex phases of syndiotactic polystyrene. J. Mat. Chem. 2007, 17, 531-535.
76. Sheng, Wang S.; Choi, M.-S.; Kim, S.-H. Multiple switching photochromic poly(N-isopropylacrylamide) with spironaphthoxazine hydrogel. Dyes Pigm. 2008, 78, 8-14.
77. Sakai, H.; Ebana, H.; Sakai, K.; Tsuchiya, K.; Ohkubo, T.; Abe, M. Photo-isomerization of spiropyran-modified cationic surfactants. J. Colloid Interface Sci. 2007, 316, 1027-1030.
78. Keum, S.-R.; Roh, S.-J.; Ahn, S.-M.; Lim, S.-S.; Kim, S.-H.; Koh, K. Solvatochromic behavior of non-activated indolinobenzospiropyran-6-carboxylates in aqueous binary solvent mixtures: part 2. Dyes Pigm. 2007, 74, 343-347.
79. Li, L.; Yu, M.X.; Li, F.Y.; Yi, T.; Huang, C.H. Inhibit logic gate based on spiropyran sensitized semiconductor electrode. Colloids Surf. A Physicochem. Eng. Asp. 2007, 304, 49-53.
80. Suh, H.-J.; Lim, W.-T.; Cui, J.-Z.; Leeb, H.-S.; Kim, G.-H.; Heo, N.-H.; Kim, S.-H. The crystalline-state photochromism, thermochromism and X-ray structural characterization of a new spiroxazine. Dyes Pigm. 2002, 57, 149-159.
81. Keum, S.-R.; Choi, Y.-K.; Kim, S.-H.; Yoon, C.-M. Symmetric and unsymmetric indolinobenzospiropyran dimers: synthesis and characterization. Dyes Pigm. 1999, 41, 41-47.
82. Chernyshev, A.V.; Voloshin, N.A.; Raskita, I.M.; Metelista, A.V.; Minkin, V.I. Photo- and ionochromism of 5'-(4,5-diphenyl-1,3-oxazol-2-yl) substituted spiro[indoline-naphthopyrans]. J. Photochem. Photobiol. A: Chem. 2006, 184, 189-297.
83. Chibisov, A.K.; Görner, H. Complexes of spiropyran-derived merocyanines with metal ions: relaxation kinetics, photochemistry and solvent effects. Chem. Phys. 1998, 237, 425-442.
84. Moniruzzaman, M.; Fernando, G.F.; Bellamy, A.J. Synthesis and structural investigation of 1′,3′,3′-trimethyl-6-hydroxy-spiro(2H- 1benzopyran-2,2′-indoline),1′,3′,3′-trimethyl-6-metha cryloxy-spiro(2H-1-benzopyran-2,2′-indoline) and a copolymer with methyl methacrylate by 1D and 2D NMR spectroscopy. Europ. Polym. J. 2006, 42, 1455-1466.
85. Li, X.; Li, J.; Wang, Y.; Matsuura, T.; Meng, J. Synthesis of functionalized spiropyran and spirooxazine derivatives and their photochromic properties. J. Photochem. Photobiol. A: Chem. 2004, 161, 201-213.
86. Toman, P.; Bartkowiak, W.; Nešpůrek, S.; Sworakowski, J.; Zaleśny, R. Quantum-chemical insight into the design of molecular optoelectrical switch. Chem. Phys. 2005, 316, 267-278.
87. Godsi, O.; Peskin, U.; Kapon, M.; Natan, E.; Eichen, Y. Site effects in controlling the chemical reactivity in crystals: solid-state photochromism of N-(n-propyl)nitrospiropyrane. Chem. Commun. 2001, 2132-2133.
88. Kawanishi, Y.; Seki, K.; Tamaki, T.; Sakuragi, M.; Suzuki, Y. Tuning reverse ring closure in the photochromic and thermochromic transformation of 1′,3′,3′-trimethyl-6-nitrospiro[2H-1-benzopyran-2, 2′-indole] analogues by ionic moieties. J. Photochem. Photobiol. A: Chem. 1997, 109, 237-242.
89. Hadjoudis, E.; Mavridis, I.M. Photochromism and thermochromism of Shiff bases in the solid state: structural aspects. Chem. Soc. Rev. 2004, 33, 279-588.
90. Maafi, M.; Brown, R.G. General analytical solutions for the kinetics of AB (k,φ) and ABC(k,φ) systems. Int. J. Chem. Kinet. 2005, 37, 162-174.
91. Maafi, M. Comment on "photokinetic methods: A mathematical analysis of the rate equations in photochromic systems" by G.Ottavi, F.Ortica, and G. Favaro (Int J Chem Kinet, 1999, 31, 303-313) Int. J. Chem. Kinet. 2008, 40, 524-525.
92. Maafi, M.; Brown, R.G. An analytical solution for the kinetics of AB (1k,1φ) systems and its application to a spirobenzopyran. Int. J. Chem. Kinet. 2007, 39, 539-545.
93. Maafi, M.; Brown, R.G. The kinetic model for AB(1φ) systems. A closed-form integration of the differential equation with a variable photokinetic factor. J. Photochem. Photobiol. A: Chem. 2007, 187, 319-324.
94. Maafi, M.; Brown, R.G. Kinetic analysis and elucidation options for AB (1k, 2φ) systems. New spectrokinetic methods for photochromes. Photochem. Photobiol. Sci (in press).
95. Maafi, M.; Brown, R.G.; A mathematical analysis and elucidation of AB (2k, 1φ) thermophotochromic kinetics. Analytical solutions using pure kinetic data and considering as unknown the rate constants, quantum yield and both species' spectra. Int. J. Chem. Kinet (in press).
96. Vajda, S.; Rabitz, H. Identifiability and distinguishability of first-order reaction systems. J. Phys. Chem. 1988, 92, 701-707.
97. Schwaab, M.; Monteiro, J.L.; Pinto, J.C. Sequential experimental design for model discrimination taking into account the posterior covariance matrix of differences between model predictions. Chem. Eng. Sci. 2008, 63, 2408-2419.
98. Maafi, M.; Brown, R.G.; Analysis of diarylnaphthopyran kinetics. Degeneracy of the kinetic solution. Int. J. Chem. Kinet. 2005, 37, 717-727.
99. Maafi, M.; Brown, R.G.; Analysis of diarylnaphthopyran kinetics. Degeneracy of the kinetic solution. Int. J. Chem. Kinet. 2005, 37, 717-727.
100. Maafi, M.; Brown, R.G.; A fundamental system of equations to describe ABC (3k, 6φ) dynamics. A contribution to the elucidation of [2H]-naphthopyran kinetics. Int. J. Chem. Kinet. 2008, 40, 269-281.