Crystal phase transition and solid-state photoisomerization of benzyl (Z,Z)-muconate polymorphs studied by direct observation of crystal structure change

Crystal Growth and Design

Volumn 10, Issue 7, 2010, Pages 3203-3210

  Nishizawa, Natsuko ^a   Furukawa, Daisuke ^a   Kobatake, Seiya ^a   Matsumoto, Akikazu ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL PHASE TRANSITION; DIRECT OBSERVATION; IN-SITU; MOLECULAR MOTIONS; PHOTO-IRRADIATION; POLYMORPH CRYSTALS; SINGLE-CRYSTAL STRUCTURE ANALYSIS; SPACE GROUPS; STRUCTURAL STRAIN; TOPOCHEMICAL REACTION;

CRYSTAL LATTICES; CRYSTALS; DIFFERENTIAL SCANNING CALORIMETRY; ISOMERS; OLEFINS; OPTICAL MICROSCOPY; PHOTOISOMERIZATION; POLYMORPHISM; THERMODYNAMICS; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

PHASE TRANSITIONS;

EID: 79251514963     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg100341g     Document Type: Article

References (92)

1. (a) Kandori, H.; Shichida, Y.; Yoshizawa, T. Biochem. (Moscow) 2001, 66, 1197-1209.
2. (b) Gasćon, J. A.; Sproviero, E. M.; Batista, V. S. Acc. Chem. Res. 2006, 39, 184-193.
3. (c) Weingart, O. J. Am. Chem. Soc. 2007, 129, 10618-10619.
4. (d) Schapiro, I.; Weingart, O.; Buss, V. J. Am. Chem. Soc. 2009, 131, 16-17.
5. (a) Warshel, A. Nature 1976, 260, 679-683.
6. (b) Warshel, A.; Barboy, N. J. Am. Chem. Soc. 1982, 104, 1469-1476.
7. (a) Harada, J.; Ogawa, K. Top. Stereochem. 2006, 25, 31-47.
8. (b) Harada, J.; Ogawa, K. Chem. Soc. Rev. 2009, 38, 2244-2252.
9. (a) Saltiel, J.; Krishna, T. S. R.; Clark, R. J. J. Phys. Chem. A 2006, 110, 1694-1697.
10. (b) Saltiel, J.; Krishna, T. S. R.; Turek, A. M.; Clark, R. J. Chem. Commun. 2006, 1506-1508.
11. (c) Saltiel, J.; Bremer,M. A.; Laohhasurayotin, S.; Krishna, T. S. R. Angew, Chem. Int. Ed. 2008, 47, 1237-1240.
12. (d) Saltiel, J.; Krishna, T. S. R.; Laohhasurayotin, S.; Fort, K.; Clark, R. J. J. Phys. Chem. A 2008, 112, 199-209.
13. Harada, J.; Uekusa, H.; Ohashi, Y. J. Am. Chem. Soc. 1999, 121, 5809-5810.
14. (a) Harada, J.; Ogawa, K. J. Am. Chem. Soc. 2001, 123, 10884-10888.
15. (b) Harada, J.; Ogawa, K. J. Am. Chem. Soc. 2004, 126, 3539-3544.
16. (c) Sokolov, A. N.; Swenson, D. C.; MacGIllivray, L. R. Proc. Nat. Acad. Sci. U.S.A. 2008, 105, 1794-1797.
17. (a) Khuong, T. -A. V.; Zepeda, G.; Sanrame, C. N.; Dang, H.; Bartberger, M. D.; Houk, K. N.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2004, 126, 14778-14786.
18. (b) Boyd, R. H.; Breitling, S. M. Macromolecules 1974, 7, 855-862.
19. (c) Jones, A. A.; Stockmayer, W. H. J. Polym. Sci., Polym. Phys. Ed. 1977, 15, 847-861.
20. Liu, R. S. H.; Asato, A. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 259-263.
21. (a) Liu, R. S. H.; Mead, D.; Asato, A. J. Am. Chem. Soc. 1985, 107, 6609-6614.
22. (b) Müller,A. M.; Lochbrunner, S.; Schimd,W. E.; Fuß,W. Angew. Chem., Int. Ed. 1998, 37, 505-507.
23. (c) Liu, R. S. H. Acc. Chem. Res. 2001, 34, 555-562.
24. (d) Liu, R. S. H. Photochem. Photobio. 2002, 76, 580-583.
25. (e) Liu, R. S. H.; Hammond, G. S. Acc. Chem. Res. 2005, 38, 396-403.
26. (f) Liu, R. S. H.; Yang, L.-Y.; Liu, J. Photochem. Photobio. 2007, 83, 2-10.
27. (a) Yang, L.-Y.; Liu, R. S. H.; Boarman, K. J.; Wendt, N. L.; Liu, J. J. Am. Chem. Soc. 2005, 127, 2404-2405.
28. (b) Yang, L.-Y.; Liu, R. S. H.; Wendt, N. L.; Liu, J. J. Am. Chem. Soc. 2005, 127, 9378-9379.
29. Saltiel has criticized the use of the term OBF because the implied 180° rotation is misleading.4 Unsaturated molecules with the Z configuration often have a nonplanar structure in the ground state and require a small change in geometry during the isomerization process to the orthogonal geometry that usually corresponds to the global minimum in the excited state. Hehas asserted the use ofOBT as the more accurate term because it does not imply a specific rotation angle. In this paper, however, we use the widely accepted OBF term.
30. (a) Saltiel, J.; Sun, Y. -P. In Photochromism, Molecules and Systems; Dürr, H.; Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990, pp 64-164.
31. (b) Waldeck, D. H. Chem. Rev. 1991, 91, 415-436.
32. (c) Arai, T.; Tokumaru, K. Chem. Rev. 1993, 93, 23-39.
33. (d) Dugave, C.; Demange, L. Chem. Rev. 2003, 103, 2475-2532.
34. (e) Das, S.; Varghese, S.; Kumar, N. S. S. Langmuir 2010, 26, 1598-1609.
35. (a) Sonoda, Y.; Kawanishi, Y.; Tsuzuki, S.; Goto, M.J. Org. Chem. 2005, 70, 9755-9763.
36. (b) Saltiel, J.; Padadimitriou, D.; Krishna, T. S. R.; Huang, Z. -N.; Krishnamoorthy, G.; Laohhasurayotin, S.; Clark, R. J. Angew. Chem., Int. Ed. 2009, 48, 8082-8085.
37. Zhao, Y. -P.; Yang, L. -Y.; Simmons, C. J.; Liu, R. S. H. Chem. Asian J. 2009, 4, 754-760.
38. (a) Matsumoto, A.; Matsumura, T.; Aoki, S. J. Chem. Soc., Chem. Commun. 1994, 1389-1390.
39. (b) Matsumoto, A.; Odani, T. Macromol. Rapid Commun. 2001, 22, 1195-1215.
40. (c) Matsumoto, A. Prog. React. Kinet. Mech. 2001, 26, 59-110.
41. (d) Matsumoto, A. Polym. J. 2003, 35, 93-121.
42. (e) Matsumoto, A. Top. Curr. Chem. 2005, 254, 263-305.
43. (a) Matsumoto, A.; Odani, T.; Chikada, M; Sada, K.; Miyata, M. J. Am. Chem. Soc. 1999, 121, 11122-11129.
44. (b) Matsumoto, A.; Nagahama, S.; Odani, T. J. Am. Chem. Soc. 2000, 122, 9109-9119.
45. (c) Matsumoto, A.; Odani, T.; Sada, K.; Miyata, M.; Tashiro, K. Nature 2000, 405, 328-330.
46. (d) Matsumoto, A.; Tanaka, T.; Tsubouchi, T.; Tashiro, K.; Saragai, S.; Nakamoto, S. J. Am. Chem. Soc. 2002, 124, 8891-8902.
47. (a) Mori, Y.; Matsumoto, A. Cryst. Growth Des. 2007, 7, 377-385.
48. (b) Mori, Y.; Matsumoto, A. Chem. Lett. 2007, 36, 510-511.
49. (a) Matsumoto, A.; Odani, T.; Yokoi, K. Proc. Jpn. Acad. Ser. B 1998, 74, 110-115.
50. (b) Odani, T.; Matsumoto, A.; Sada, K.; Miyata, M. Chem. Commun. 2001, 2004-2005.
51. (c) Saragai, S.; Tashiro, K.; Nakamoto, S.; Matsumoto, A.; Tsubouchi, T. J. Phys. Chem. B 2001, 105, 4155-4165.
52. (a) Cohen, M. D.; Schmidt, G. M. J.; Sonntag, F. I. J. Chem. Soc. 1964, 2000.
53. (b) Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433-481.
54. (c) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids: Elsevier: Amsterdam, 1989.
55. (d) Ramamurthy, V., Ed. Photochemistry in Organized & ConstrainedMedia: VCH: New York, 1991.
56. (e) Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025-1074.
57. (f) Khuong, T. A. V.; Nunez, J. E.; Godinez, C. E.; Garcia-Garibay, M. A. Acc. Chem. Res. 2006, 39, 413-422.
58. (g) MacGillivray, L. R.; Papaefstahiou, G. S.; Frišč ić, T.; Varshney, D. B.; Hamilton, T. D. Top. Curr. Chem. 2004, 248, 201-221.
59. (h) Braga, D.; Grepioni, F. Chem. Commun. 2005, 3635-3645.
60. (i) Toda, F., Ed. Top. Curr. Chem. Vol. 254, Organic Solid State Reactions Springer: Berlin, 2005.
61. (j) Braga, D.; Grepioni, F., Eds., Making Crystals by Design: Methods, Techniques and Applications: Wiley-VCH: Weinheim, 2007.
62. (a) Alfimov, S. M.; Razumov, V. F. Mol. Cryst. Liq. Cryst. 1978, 49, 95-97.
63. (b) Aldoshin, S. M.; Alfimov, M. V.; Atovmyan, L. O.; Kaminsky, V. F.; Razumov, V. F.; Rachinsky, A. G. Mol. Cryst. Liq. Cryst. 1984, 108, 1-17.
64. Moorthy, J. N.; Venkatakrishnan, P.; Savitha, G.; Weiss, R. G. Photochem. Photobio. Sci. 2006, 5, 903-913.
65. (a) Kinbara, K.; Kai, A.; Maekawa, Y.; Hashimoto, Y.; Naruse, S.; Hasegawa, M.; Saigo, K. J. Chem. Soc., Perkin Trans. 2 1996, 247-253.
66. (b) Kinbara, K.; Saigo, K. Bull. Chem. Soc. Jpn. 1996, 69, 779-784.
67. (c) Bogadi, R. S.; Levendis, D. C.; Coville, N. J. J. Am. Chem. Soc. 2002, 124, 1104-1110.
68. (d) Natarajan, A.;Mague, J. T.;Venkatesan, K.; Arai, T.; Ramamurthy, V. J. Org. Chem. 2006, 71, 1055-1059.
69. (a) Cohen, M. D. Angew. Chem., Int. Ed. Engl. 1975, 14, 386-393.
70. (b) Gavezzotti, A. J. Am. Chem. Soc. 1983, 105, 5220-5225.
71. (c) Ohashi, Y. Acc. Chem. Res. 1988, 21, 268-274.
72. (d) Zimmerman, H. E.; Alabugin, I. V.; Chen,W.; Zhu, Z. J. Am. Chem. Soc. 1999, 121, 11930-11931.
73. (e) Brett, T. J.; Alexander, J. M.; Clark, J. L.; Ross, C. R., II; Harbison, G. S.; Stezowski, J. J. Chem. Commun. 1999, 1275-1278.
74. (f) Ohhara, T.; Ikeda, S.; Imura, H.; Uekusa, H.; Ohashi, Y.; Tanaka, I.; Niimura, N. J. Am. Chem. Soc. 2002, 124, 14736-14740.
75. (g) Garcia- Garibay, M. A. Acc. Chem. Res. 2003, 36, 491-498.
76. (a) McBride, J. M. Acc. Chem. Res. 1983, 16, 304-312.
77. (b) McBride, J. M.; Segmuller,B. E.; Hollingsworth, M. D.; Mills, D. E.;Weber,B.A. Science 1986, 234, 830-835.
78. (c) Weiss, R. G.; Ramamurthy, V.; Hammond, G. S. Acc. Chem. Res. 1993, 26, 530-536.
79. (d) Kaupp, G. Photochem. Photobio. 2002, 76, 590-595.
80. Furukawa, D.; Kobatake, S.; Matsumoto, A. Chem. Commun. 2008, 55-57.
81. (a) Molecular Nano Dynamics vol 2, Active Surfaces, Single Crystals and Single Biocells eds. Fukumura, H; Irie, M; Iwasawa, Y.; Masuhara, H.; Uosaki, K.Wiley-VCH: Weinheim, 2009.
82. (b) Kim, C. D.; Pillet, S.; Wu, G.; Fullagar, W. K.; Coppens, P. Acta Crystallogr., Sect. A 2002, 58, 133-137.
83. (c) Coppens, P. Chem. Commun. 2003, 1317-1320.
84. (d) Kobatake, S.; Irie, M. Bull. Chem. Soc. Jpn. 2004, 77, 195-210.
85. (e) Zheng, S. -L.;Messerschmidt,M.; Coppens, P. Chem. Commun. 2007, 2735-2737.
86. (f) Kawano, M.; Hirai, K.; Tomioka, H.; Ohashi, Y. J. Am. Chem. Soc. 2007, 129, 2383-2391.
87. (g) Zheng, S. -L.; Velde, C. M. L. V.; Messerschmidt, M.; Volkov, A.; Gembicky, M.; Coppens, P. Chem.-Eur. J. 2008, 14, 706-713.
88. (h) Furukawa, D.; Matsumoto, A. Macromolecules 2007, 40, 6048-6056.
89. (i) Li, Z.; Fowler, F.W.; Lauher, J.W. J. Am. Chem. Soc. 2009, 131, 634-643.
90. Sheldrick, G. M. SHELXL97; Institüt für Anorganische Chemie der Universität: Gottingen, Germany, 1997.
91. Matsumoto, A.; Tanaka, T.; Oka, K. Synthesis 2005, 1479-1489.
92. Enkelmann, V.; Wegner, G.; Novak, K.; Wagener, K. B. J. Am. Chem. Soc. 1993, 115, 10390-10391