Multistate photochromism of 1-phenylnaphthalene-bridged imidazole dimer that has three colorless isomers and two colored isomers

Journal of Physical Chemistry A

Volumn 118, Issue 1, 2014, Pages 134-143

  Yamaguchi, Tetsuo ^a   Hatano, Sayaka ^b   Abe, Jiro ^a,c  

^a AOYAMA GAKUIN UNIVERSITY   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELEVATED TEMPERATURE; LIGHT IRRADIATIONS; MOLECULAR PROPERTIES; PHOTOCHROMIC MOLECULES; ROOM TEMPERATURE; THERMOCHEMICAL PROPERTIES; VISIBLE-LIGHT IRRADIATION; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

DIMERS; MOLECULES; PHOTOCHROMISM; PLANTS (BOTANY); SMECTIC LIQUID CRYSTALS; X RAY CRYSTALLOGRAPHY;

ISOMERS;

EID: 84892563748     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp411190d     Document Type: Article

References (75)

1. Hayashi, T.; Maeda, K. Preparation of a New Phototropic Substance Bull. Chem. Soc. Jpn. 1960, 33, 565-566
2. White, D. M.; Sonnenberg, J. Oxidation of Triarylimidazoles. Structures of the Photochromic and Piezochromic Dimers of Triarylimidazyl Radicals J. Am. Chem. Soc. 1966, 88, 3825-3829
3. Maeda, K.; Hayashi, T. Photochromic Color Change of the Dimer of Triphenylimidazolyl at Low Temperatures Bull. Chem. Soc. Jpn. 1969, 42, 3509-3514
4. Shida, T.; Maeda, K.; Hayashi, T. Optical and ESR Studies on Triphenylimidazolyl Radicals Produced by Photolysis and Radiolysis at Low Temperature Bull. Chem. Soc. Jpn. 1970, 43, 652-657
5. Cohen, R. L. Substituent Effect on the Reactivity of Triphenylimidazolyl Free Radicals toward Tris(2-Methyl-4-Diethylaminophenyl)Methane J. Org. Chem. 1971, 36, 2280-2284
6. Riem, R. H.; MacLachlan, A.; Coraor, G. R.; Urban, E. J. The Flash Photolysis of a Substituted Hexaarylbiimidazole and Reactions of the Imidazolyl Radical J. Org. Chem. 1971, 36, 2272-2275
7. Cescon, L. A.; Coraor, G. R.; Dessauer, R.; Silversmith, E. F.; Urban, E. J. Some Properties of Triarylimidazolyl Radicals and Their Dimers J. Org. Chem. 1971, 36, 2262-2267
8. Tanino, H.; Kondo, T.; Okada, K.; Goto, T. Structures of Three Isomeric Dimers of 2,4,5-Triphenylimidazolyl Bull. Chem. Soc. Jpn. 1972, 45, 1474-1480
9. Qin, X.-Z.; Liu, A.-D.; Trifunac, A. D.; Krongauz, V. V. Photodissociation of Hexaarylbiimidazole. 1. Triplet-State Formation J. Phys. Chem. 1991, 95, 5822-5826
10. Liu, A.-D.; Trifunac, A. D.; Krongauz, V. V. Photodissociation of Hesaarylbiimidazole. 2. Direct and Sensitized Dissociation J. Phys. Chem. 1992, 96, 207-211
11. Kawano, M.; Sano, T.; Abe, J.; Ohashi, Y. The First in Situ Direct Observation of the Light-Induces Radical Pair from a Hexaarylbiimidazolyl Derivative by X-ray Crystallography J. Am. Chem. Soc. 1999, 121, 8106-8107
12. Kawano, M.; Sano, T.; Abe, J.; Ohashi, Y. In situ Observation of Molecular Swapping in a Crystal by X-ray Analysis Chem. Lett. 2000, 29, 1372-1373
13. Abe, J.; Sano, T.; Kawano, M.; Ohashi, Y.; Matsushita, M. M.; Iyoda, T. EPR and Density Functional Studies of Light-Induced Radical Pairs in a Single Crystal of a Hexaarylbiimidazolyl Derivative Angew. Chem., Int. Ed. 2001, 40, 580-582
14. Kikuchi, A.; Iyoda, T.; Abe, J. Electronic Structure of Light-Induced Lophyl Radical Derived from A Novel Hexaarylbiimidazole with π-Conjugated Chromophore Chem. Commun. 2002, 38, 1484-1485
15. Kikuchi, A.; Iwahori, F.; Abe, J. Definitive Evidence for the Contribution of Biradical Character in a 1,4-Bis-(4,5-Diphenylimidazole-2- ylidene)Cyclohexa-2,5-Diene J. Am. Chem. Soc. 2004, 126, 6526-6527
16. Miyamoto, Y.; Kikuchi, A.; Iwahori, F.; Abe, J. Synthesis and Photochemical Properties of a Photochromic Iron(II) Complex of Hexaarylbiimidazole J. Phys. Chem. A 2005, 109, 10183-10188
17. Miyasaka, H.; Satoh, Y.; Ishibashi, Y.; Ito, S.; Nagasawa, Y.; Taniguchi, S.; Chosrowjan, H.; Mataga, N.; Kato, D.; Kikuchi, A. Ultrafast Photodissociation Dynamics of a Hexaarylbiimidazole Derivative with Pyrenyl Groups: Dispersive Reaction from Femtosecond to 10 ns Time Regions J. Am. Chem. Soc. 2009, 131, 7256-7263
18. Kimoto, A.; Niitsu, A.; Iwahori, F.; Abe, J. Formation of Hexaarylbiimidazole Heterodimers via The Cross Recombination of Two Lophyl Radicas New J. Chem. 2009, 33, 1339
19. Kikuchi, A.; Harada, Y.; Yagi, M.; Ubukata, T.; Yokoyama, Y.; Abe, J. Photoinduced Diffusive Mass Transfer in o -Cl-HABI Amorphous Thin Films Chem. Commun. 2010, 46, 2262-2264
20. Kishimoto, Y.; Abe, J. A Fast Photochromic Molecule That Colors Only under UV Light J. Am. Chem. Soc. 2009, 131, 4227-4229
21. Harada, Y.; Hatano, S.; Kimoto, A.; Abe, J. Remarkable Acceleration for Back-Reaction of a Fast Photochromic Molecule J. Phys. Chem. Lett. 2010, 1, 1112-1115
22. Kimoto, A.; Tokita, A.; Horino, T.; Oshima, T.; Abe, J. Fast Photochromic Polymers Carrying [2.2]Paracyclophane-Bridged Imidazole Dimer Macromolecules 2010, 43, 3764-3769
23. Mutoh, K.; Hatano, S.; Abe, J. An Efficient Strategy for Enhancing the Photosensitivity of Photochromic [2.2]Paracyclophane-Bridged Imidazole Dimers J. Photopolym. Sci. Technol. 2010, 23, 301-306
24. Hatano, S.; Sakai, K.; Abe, J. Unprecedented Radical-Radical Reaction of a [2.2]Paracyclophane Derivative Containing an Imidazolyl Radical Moiety Org. Lett. 2010, 12, 4152-4155
25. Takizawa, M.; Kimoto, A.; Abe, J. Photochromic Organogel Based on [2.2]Paracyclophane-Bridged Imidazole Dimer with Tetrapodal Urea Moieties Dyes Pigm. 2011, 89, 254-259
26. Mutoh, K.; Abe, J. Comprehensive Understanding of Structure- Photosensitivity Relationships of Photochromic [2.2]Paracyclophane-Bridged Imidazole Dimers J. Phys. Chem. A 2011, 115, 4650-4646
27. Mutoh, K.; Abe, J. Photochromism of A Water-Soluble Vesicular [2.2]Paracyclophane-Bridged Imidazole Dimer Chem. Commun. 2011, 47, 8868-8870
28. Yamashita, H.; Abe, J. Photochromic Properties of [2.2]Paracyclophane- Bridged Imidazole Dimer with Increased Photosensitivity by Introducing Pyrenyl Moiety J. Phys. Chem. A 2011, 115, 13332-13337
29. Mutoh, K.; Nakano, E.; Abe, J. Spectroelectrochemistry of a Photochromic [2.2]Paracyclophane-Bridged Imidazole Dimer: Clarification of the Electrochemical Behavior of HABI J. Phys. Chem. A 2011, 116, 6792-6797
30. Ishii, N.; Kato, T.; Abe, J. A Real-Time Dynamic Holographic Material Using a Fast Photochromic Molecule Sci. Rep. 2012, 2, 819-824
31. Kawai, S.; Yamaguchi, T.; Kato, T.; Hatano, S.; Abe, J. Entropy-Controlled Thermal Back-Reaction Of Photochromic [2.2]Paracyclophane- Bridged Imidazole Dimer Dyes Pigm. 2012, 92, 872-876
32. Mutoh, K.; Sliwa, M.; Abe, J. Rapid Fluorescence Switching by Using a Fast Photochromic [2.2]Paracyclophane-Bridged Imidazole Dimer J. Phys. Chem. C 2013, 117, 4808-4814
33. Iwahori, F.; Hatano, S.; Abe, J. Rational Design of a New Class of Diffusion-Inhibited HABI with Fast Back-Reaction J. Phys. Org. Chem. 2007, 20, 857-863
34. Fujita, K.; Hatano, S.; Kato, D.; Abe, J. Photochromism of a Radical Diffusion-Inhibited Hexaarylbiimidazole Derivative with Intense Coloration and Fast Decoloration Performance Org. Lett. 2008, 10, 3105-3108
35. Hatano, S.; Abe, J. Activation Parameters for the Recombination Reaction of Intramolecular Radical Pairs Generated from the Radical Diffusion-Inhibited HABI Derivative J. Phys. Chem. A 2008, 112, 6098-6103
36. Hatano, S.; Fujita, K.; Tamaoki, N.; Kaneko, T.; Nakashima, T.; Naito, M.; Kawai, T.; Abe, J. Reversible Photogeneration of a Stable Chiral Radical-Pair from a Fast Photochromic Molecule J. Phys. Chem. Lett. 2011, 2, 2680-2682
37. Hatano, S.; Abe, J. A Peroxide-Bridged Imidazole Dimer Formed from a Photochromic Naphthalene-Bridged Imidazole Dimer Phys. Chem. Chem. Phys. 2012, 14, 5855-5860
38. Mutoh, K.; Shima, K.; Yamaguchi, T.; Kobayashi, M.; Abe, J. Photochromism of a Naphthalene-Bridged Imidazole Dimer Constrained to the "Anti" Conformation Org. Lett. 2013, 15, 2938-2941
39. Shimizu, I.; Kokado, H.; Inoue, E. Photoreversible Photographic Systems. VI. Reverse Photochromism of 1,3,3-Trimethylspiro[Indoline-2,2′- Benzopyran]-8′-Carboxylic Acid Bull. Chem. Soc. Jpn. 1969, 42, 1730-1734
40. Inoue, E.; Kokado, H.; Shimizu, I.; Kobayashi, H. Photo-Decoloration Process of the Reverse Photochromic Spirans Bull. Chem. Soc. Jpn. 1972, 45, 1951-1956
41. Namba, K.; Shimizu, I. Normal and Reverse Photochromism of 1-(β -Carboxyethyl)-3,3-Dimethyl-6′-Nitrospiro[Indoline-2,2′-2 H -Benzopyran] in Water-Dioxane Bull. Chem. Soc. Jpn. 1975, 48, 1323-1324
42. Sunamoto, J.; Iwamoto, K.; Akutagawa, M.; Nagase, M.; Kondo, H. Rate Control by Restricting Mobility of Substrate in Specific Reaction Field. Negative Photochromism of Water-Soluble Spiropyran in AOT Reversed Micelles J. Am. Chem. Soc. 1982, 104, 4904-4907
43. Ciardelli, F.; Fabbri, D.; Pieroni, O.; Fissi, A. Photomodulation of Polypeptide Conformation by Sunlight in Spiropyran-Containing Poly(L-Glutamic acid) J. Am. Chem. Soc. 1989, 111, 3470-3472
44. Inouye, M.; Ueno, M.; Kitao, T. Alkali Metal Recognition Induced Isomerization of Spiropyrans J. Am. Chem. Soc. 1990, 112, 8977-8979
45. Hirano, M.; Miyashita, A.; Shitara, H.; Nohira, H. Synthesis and Photochemical Properties of Novel Spirobenzoselenazolinobenzopyrans Chem. Lett. 1991, 20, 1873-1876
46. Takagi, K.; Kurematsu, T.; Sawaki, Y. Intercalation and Photochromism of Spiropyrans on Clay Interlayers J. Chem. Soc., Perkin Trans. 2 1991, 10, 1517-1522
47. Nakano, S.; Miyashita, A.; Nohira, H. Metastable Solution Structures of Spirobenzoselenazolinobenzopyrans and Their Negative Photochromic Properties Chem. Lett. 1993, 22, 13-16
48. Yokoyama, Y.; Shiroyama, T. Negative Photochromism of 3.1'-Trimethylene-Bridged 6-Nitroindolinospiropyran Chem. Lett. 1995, 24, 71-72
49. Fissi, A.; Pieroni, O.; Ruggeri, G.; Ciardelli, F. Photoresponsive Polymers. Photomodulation of the Macromolecular Structure in Poly(L-Lysine) Containing Spiropyran Units Macromolecules 1995, 28, 302-309
50. Takagi, K.; Kurematsu, T.; Sawaki, Y. Photochromic Behavior of Surfactant Spiro[2H- 1- Benzopyran- 2, 2′- [2, 3]-Dihydroindole]s (Spiropyrans) Adsorbed into Clay Interlayers J. Chem. Soc., Perkin Trans. 2 1995, 8, 1667-1671
51. Minami, M.; Taguchi, N. Effects of Substituents on the Indoline Ring on the Negative Photochromic Properties of Soirobenzopyran Derivatives Chem. Lett. 1996, 25, 429-430
52. Suzuki, T.; Lin, F.-T.; Priyadashy, S.; Weber, S. G. Stabilization of the Merocyanine form of Photochromic Compounds in Fluoro Alcohols Is due to a Hydrogen Bond Chem. Commun. 1998, 24, 2685-2686
53. Tanaka, M.; Nakamura, M.; Salhin, M. A. A.; Ikeda, T.; Kamada, K.; Ando, H.; Shibutani, Y.; Kimura, K. Synthesis and Photochromism of Spirobenzopyran Derivatives Bearing an Oxymethylcrown Ether Moiety: Metal Ion-Induced Switching between Positive and Negative Photochromisms J. Org. Chem. 2001, 66, 1533-1537
54. Pieroni, O.; Fissi, A.; Angelini, N.; Lenci, F. Photoresponsive Polypeptides Acc. Chem. Res. 2001, 34, 9-17
55. Tanaka, M.; Ikeda, T.; Xu, Q.; Ando, H.; Shibutani, Y.; Nakamura, M.; Sakamoto, H.; Yajima, S.; Kimura, K. Synthesis and Photochromism of Spirobenzopyrans and Spirobenzothiapyran Derivatives Bearing Monoazathiacrown Ethers and Noncyclic Analogues in the Presence of Metal Ions J. Org. Chem. 2002, 67, 2223-2227
56. Yokoyama, Y.; Hara, W.; Inoue, T.; Ubukata, T.; Sakomura, M.; Tukada, H. Negative Photochromism of a Spiropyran in a Langmuir-Blodgett Film Chem. Lett. 2005, 34, 1622-1623
57. Keum, S.-R.; Roh, S.-J.; Kim, S.-E.; Lee, S.-H.; Cho, C.-H.; Kim, S.-H.; Koh, K.-N. Unusual Reverse Photochromic Behavior of Indolinobenzospiropyran 6-Carboxylates in Aqueous Binary Solvents Bull. Korean Chem. Soc. 2006, 27, 187-188
58. Tomasulo, M.; Yildiz, I.; Raymo, F. M. Nanoparticle-Induced Transition from Positive to Negative Photochromism Inorg. Chim. Acta 2007, 360, 938-944
59. Zhang, C.; Zhang, Z.; Fan, M.; Yan, W. Positive and Negative Photochromism of Novel Spiro[Indoline-Phenanthrolinoxazines] Dyes Pigm. 2008, 76, 832-835
60. Sakai, K.; Imaizumi, Y.; Oguchi, T.; Sakai, H.; Abe, M. Adsorption Characteristics of Spiropyran-Modified Cationic Surfactants at the Silica/Aqueous Solution Interface Langmuir 2010, 26, 9283-9288
61. Mitchell, R. H.; Ward, T. R.; Chen, Y.; Wang, Y.; Weerawarna, S. A.; Dibble, P. W.; Marsella, M. J.; Almutairi, A.; Wang, Z.-Q. Synthesis and Photochromic Properties of Molecules Containing [ e ]-Annelated Dihydropyrenes. Two and Three Way π-Switches Based on the Dimethyldihydropyrene- Metacyclophanediene Valence Isomerization J. Am. Chem. Soc. 2003, 125, 2974-2988
62. Kobayashi, M.; Takashima, A.; Ishii, T.; Naka, H.; Uchiyama, M.; Yamaguchi, K. Reverse Photochromic Behavior of an Iron-Magnesium Complex Inorg. Chem. 2007, 46, 1039-1041
63. Irie, M.; Fukaminato, T.; Tanaka, M. Japan Patent JP 2009-062344 A, 2009.
64. Fukaminato, T.; Doi, T.; Tanaka, M.; Irie, M. Photocyclization Reaction of Diarylethene-Perylenebisimide Dyads upon Irradiation with Visible (>500 nm) Light J. Phys. Chem. C 2009, 113, 11623-11627
65. Ayub, K.; Li, R.; Bohne, C.; Williams, R. V.; Mitchell, R. H. Calculation Driven Synthesis of an Excellent Dihydropyrene Negative Photochrome and Its Photochemical Properties J. Am. Chem. Soc. 2011, 133, 4040-4045
66. Peng, P.; Strohecker, D.; Liao, Y. Negative Photochromism of a TCF Chromophore Chem. Commun. 2011, 47, 8575-8577
67. Hatano, S.; Horino, T.; Tokita, A.; Oshima, T.; Abe, J. Unusual Negative Photochromism via a Short-Lived Imidazolyl Radical of 1,1′-Binaphthyl- Bridged Imidazole Dimer J. Am. Chem. Soc. 2013, 135, 3164-3172
68. Hanazawa, M.; Sumiya, R.; Horikawa, Y.; Irie, M. Thermally Irreversible Photochromic Systems. Reversible Photocyclization of 1,2-Bis(2-Methylbenzo[ β ]Thiophen-3-yl)Perfluorocyclocoalkene Derivatives J. Chem. Soc., Chem. Commun. 1992, 206-207
69. Wintgens, V.; Johnston, L. J.; Scaiano, J. C. Use of a Photoreversible Fulgide as an Actinometer in One- and Two-Laser Experiments J. Am. Chem. Soc. 1988, 110, 511-517
70. 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
71. Yamaguchi, T.; Uchida, K.; Irie, M. Photochromic Properties of Diarylethene Derivatives Having Benzofuran and Benzothiophene Rings Based on Regioisomers Bull. Chem. Soc. Jpn. 2008, 81, 644-652
72. Moleele, S. S.; Michael, J. P.; de Koning, C. B. Tetralones as Precursors for the Synthesis of 2,2′-Disubstituted 1,1′-Binaphthyls and Related Compounds Tetrahedron 2008, 64, 10573-10580
73. Sheldrick, G. M. SHELXS-97 and SHELXL-97; University of Gottingen: Gottingen, Germany, 1997.
74. Sheldrick, G. M. SADABS; University of Gottingen: Gottingen, Germany, 1996.
75. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2009.