Polymorphism of dehydrobenzo[14]annulene possessing two methyl ester groups in noncentrosymmetric positions

Crystal Growth and Design

Volumn 11, Issue 12, 2011, Pages 5488-5497

  Hisaki, Ichiro ^a   Kometani, Eriko ^a   Shigemitsu, Hajime ^a   Saeki, Akinori ^a,b   Seki, Shu ^a   Tohnai, Norimitsu ^a,b   Miyata, Mikiji ^a  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANNULENES; CHEMICAL DEFECTS; CONFORMATIONAL FLEXIBILITY; CRYSTALLIZATION CONDITIONS; CYCLIC COMPOUNDS; FLUORESCENCE BAND; FLUORESCENCE PROPERTIES; INTERACTION METHODS; METHYL ESTERS; NON-CENTROSYMMETRIC; POLYMORPHIC CRYSTALS; SUPRAMOLECULAR STRUCTURE;

CRYSTALS; ELECTRONIC PROPERTIES; ESTERIFICATION; ESTERS; FLUORESCENCE; NEEDLES;

CRYSTAL DEFECTS;

EID: 83055198368     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg201075z     Document Type: Article

References (93)

1. Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048
2. Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718-747
3. Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491-1546
4. Kato, T.; Mizoshita, N.; Kishimoto, K. Angew. Chem., Int. Ed. 2006, 45, 38-68
5. Würthner, F.; Kaiser, T. E.; Saha-Möller, C. R. Angew. Chem., Int. Ed. 2011, 50, 3376-3410
6. Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3440-3461
7. Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629-1658
8. Bernstein, J. Polymorphism in Molecular Crystals; Oxford University Press: New York, 2002.
9. Blagden, M.; Davey, R. J. Cryst. Growth Des. 2003, 3, 873-885
10. Desiraju, G. R. Angew. Chem., Int. Ed. 2007, 46, 8342-8356
11. Making Crystals by Design; Braga, D.; Grepioni, F., Eds.; Wiley-VCH: Weinheim, 2007.
12. Polymorphism: in the Pharmaceutical Industry; Hifiker, R., Ed.; Wiley-VCH: Weinheim, 2007.
13. Mangin, D.; Puel, F.; Veesler, S. Org. Process. Res. Dev. 2009, 13, 1241-1253
14. Kitamura, M. CrystEngComm 2009, 11, 949-964
15. Mori, T. Chem. Rev. 2004, 104, 4947-4969
16. Kobayashi, H.; Cui, H.; Kobayashi, A. Chem. Rev. 2004, 104, 5265-5288
17. Sorai, M.; Nakano, M.; Miyazaki, Y. Chem. Rev. 2006, 106, 976-1031
18. Row, T. N. G. Coord. Chem. Rev. 1999, 183, 81-100
19. Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025-1074
20. Matsumoto, A. Top. Curr. Chem. 2005, 254, 263-305
21. Morimoto, M.; Kobatake, S.; Irie, M. Chem.-Eur. J. 2003, 9, 621-627
22. Zhang, H.; Zhang, Z.; Ye, K.; Zhang, J.; Wang, Y. Adv. Mater. 2006, 18, 2369-2372
23. Yago, T.; Tamaki, Y.; Furube, A.; Katoh, R. Chem. Lett. 2007, 36, 370-371
24. Kohmoto, S.; Tsuyuki, R.; Masu, J.; Azumaya, I.; Kishikawa, K. Tetrahedron Lett. 2008, 49, 39-43
25. Mutai, T.; Tomoda, H.; Ohkawa, T.; Yabe, Y.; Araki, K. Angew. Chem., Int. Ed. 2008, 47, 9522-9524
26. Maeda, H.; Bando, Y.; Haketa, Y.; Honsho, Y.; Seki, S.; Nakajima, H.; Tohnai, N. Chem.-Eur. J. 2010, 16, 10994-11002
27. Zhang, G.; Lu, J.; Sabat, M.; Fraser, C. L. J. Am. Chem. Soc. 2010, 132, 2160-2162
28. McCrone, W. C. Polymorphism. In Physics and chemistry of the organic solid state; Fox, D.; Labes, M. M.; Weissberger, A., Eds.; Wiley Interscience: New York, 1965; pp 725-767.
29. Comprehensive reports for recent polymorphs, see: Brittain, H. G. J. Pharm. Sci. 2007, 96, 705-728
30. J. Pharm. Sci., 2008, 97, 3611-3636.
31. J. Pharm. Sci., 2009, 98, 1617-1642.
32. J. Pharm. Sci., 2010, 99, 3648-3664.
33. Jetti, R. K. R.; Boese, R.; Sarma, J. A. R. P.; Reddy, L. S.; Vishweshwar, P.; Desiraju, G. R. Angew. Chem., Int. Ed. 2003, 42, 1963-1967
34. Bis, J. A.; Vishweshwar, P.; Middleton, R. A.; Zaworotko, M. J. Cryst. Growth Des. 2006, 6, 1048-1053
35. Sokolov, A. N.; Swenson, D. C.; MacGillivray, L. R. Proc. Natl. Acad. Sci. 2008, 105, 1794-1797
36. Dey, S. K.; Das, G. Cryst. Growth Des. 2010, 10, 754-760
37. Aakeröy, C. B.; Nieuwenhuyzen, M.; Price, S. L. J. Am. Chem. Soc. 1998, 120, 8986-8993
38. Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A.; Nieuwenhuyzen, M. Cryst. Growth Des. 2003, 3, 159-165
39. Roy, S.; Matzger, A. J. Angew. Chem., Int. Ed. 2009, 48, 8505-8508
40. Li, J.; Bourne, S. A.; Caira, M. R. Chem. Commun. 2011, 47, 1530-1532
41. Yu, L. Acc. Chem. Res. 2010, 43, 1257-1266 and refs therein
42. Nangia, A. Acc. Chem. Res. 2008, 41, 595-604 and refs therein
43. Walsh, R. D. B.; Bradner, M. W.; Fleischman, S.; Morales, L. A.; Moulton, B.; Rodriguez-Hornedo, N.; Zaworotko, M. J. Chem. Commun. 2003, 2, 186-187
44. Porter, W. W., III; Elie, S. C.; Matzger, A. J. Cryst. Growth Des. 2008, 8, 14-16
45. Polymorphs of some large π-conjugated systems, such as copper phthalocyanine and pentacene, have been investigated, for example, see ref 2c and the following literature: (a) Mattheus, C. C.; Dros, A. B.; Baas, J.; Oostergetel, G. T.; Meetsma, A.; de Boer, J. L.; Palstra, T. T. M. Synth. Met. 2003, 138, 475-481
46. Cornil, J.; Lemaur, V.; Calbert, J.-P.; Brédas, J.-L. Adv. Mater. 2002, 14, 726-729
47. Lemaur, V.; da Silva Filho, D. A.; Coropceanu, V.; Lehmann, M.; Geerts, Y.; Piris, J.; Debije, M. G.; van de Craats, A. M.; Senthilkumar, K.; A Siebbeles, L. D.; Warman, J. M.; Brédas, J.-L.; Cornil, J. J. Am. Chem. Soc. 2004, 126, 3271-3279
48. Marcon, V.; Breiby, D. W.; Pisula, W.; Dahl, J.; Kirkpatrick, J.; Patwardhan, S.; Grozema, F.; Andrienko, D. J. Am. Chem. Soc. 2009, 131, 11426-11432
49. Feng, X.; Marcon, V.; Pisula, W.; Hansen, M. R.; Kirkpatrick, J.; Grozema, F.; Andrienko, D.; Kremer, K.; Müllen, K. Nat. Mater. 2009, 8, 421-426
50. Hisaki, I.; Sakamoto, Y.; Shigemitsu, H.; Tohnai, N.; Miyata, M.; Seki, S.; Saeki, A.; Tagawa, S. Chem.-Eur. J. 2008, 14, 4178-4187
51. Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Chem. Soc. Rev. 1999, 28, 107-119
52. Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153-3177
53. Jones, C. S.; O'Connor, M. J.; Haley, M. M. In Acetylene Chemistry; Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, 2005; pp 303-385.
54. Hisaki, I.; Sonoda, M.; Tobe, Y. Eur. J. Org. Chem. 2006, 833-847
55. Spitler, E. L.; Johnson, C. A., II; Haley, M. M. Chem. Rev. 2006, 106, 5344-5386
56. Sadowy, A. L.; Tykwinski, R. R. In Modern Supramolecular Chemistry; Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, 2008; pp 185-231.
57. Baldwin, K. P.; Matzger, A. J.; Scheiman, D. A.; Tessier, C. A.; Vollhardt, K. P. C.; Youngs, W. J. Synlett 1995, 1215-1218
58. Boydston, A. J.; Haley, M. M. Org. Lett. 2001, 3, 3599-3601
59. Boydston, A. J.; Haley, M. M.; Williams, R. V.; Armantrout, J. R. J. Org. Chem. 2002, 67, 8812-8819
60. Kimball, D. B.; Haley, M. M.; Mitchell, R. H.; Ward, T. R. Org. Lett. 2001, 3, 1709-1711
61. Kimball, D. B.; Haley, M. M.; Mitchell, R. H.; Ward, T. R.; Bandyopadhyay, S.; Williams, R. V.; Armantrout, J. R. J. Org. Chem. 2002, 67, 8798-8811
62. Hinrichs, H.; Fischer, A. K.; Jones, P. G.; Hopf, H.; Haley, M. M. Org. Lett. 2005, 7, 3783-3795
63. Hinrichs, H.; Boydston, A. J.; Jones, P. G.; Hess, K.; Herges, R.; Haley, M. M.; Hopf, H. Chem.-Eur. J. 2006, 12, 7103-7115
64. Marsden, J. A.; Miller, J. J.; Shirtdiff, L. D.; Haley, M. M. J. Am. Chem. Soc. 2005, 127, 2464-2476
65. Takeda, T.; Fix, A. G.; Haley, M. M. Org. Lett. 2010, 12, 3824-3827
66. Hisaki, I.; Sakamoto, Y.; Shigemitsu, H.; Tohnai, N.; Miyata, M. Cryst. Growth Des. 2009, 9, 414-420
67. Hisaki, I.; Shigemitsu, H.; Sakamoto, Y.; Hasegawa, Y.; Okajima, Y.; Nakano, K.; Tohnai, N.; Miyata, M. Angew. Chem., Int. Ed. 2009, 48, 5465-5469
68. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
69. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76
70. Desiraju, G. R. Chem. Commun. 2005, 2995-3001
71. Tanaka, A.; Inoue, K.; Hisaki, I.; Tohnai, N.; Miyata, M.; Matsumoto, A. Angew. Chem., Int. Ed. 2006, 45, 4142-4145
72. Miyata, M.; Tohnai, N.; Hisaki, I. Acc. Chem. Res. 2007, 40, 694-702
73. Wegner, G. Z. Naturforsch., B: Chem. Sci. 1969, 24, 824-832
74. Scott, J. L.; Yamada, T.; Tanaka, K. New J. Chem. 2004, 28, 447-450
75. Mizobe, Y.; Ito, H.; Hisaki, I.; Miyata, M.; Hasegawa, Y.; Tohnai, N. Chem. Commun. 2006, 2126-2128
76. Hinoue, T.; Mizobe, Y.; Hisaki, I.; Miyata, M.; Tohnai, N. Chem. Lett. 2008, 37, 642-643
77. Lai, R. Y.; Fleming, J. J.; Merner, B. L.; Vermeij, R. J.; Bodwell, G. J.; Bard, A. J. J. Phys. Chem. A 2004, 108, 376-383
78. Stevens, B. Nature 1961, 25, 725-727
79. Seki, S.; Yoshida, Y.; Tagawa, S.; Asai, K.; Ishigure, K.; Furukawa, K.; Fujiki, M.; Matsumoto, M. Philos. Mag. B 1999, 79, 1631-1645
80. Grozema, F. C.; Siebbeles, L. D. A.; Warman, J. M.; Seki, S.; Tagawa, S.; Scherf, U. Adv. Mater. 2002, 14, 228-231
81. Saeki, A.; Seki, S.; Sunagawa, T.; Usida, K.; Tagawa, S. Philos. Mag. B 2006, 86, 1261-1276
82. Saeki, A.; Seki, S.; Takenobu, T.; Iwasa, Y.; Tagawa, S. Adv. Mater. 2008, 20, 920-923
83. Yamamoto, Y.; Fukushima, T.; Suna, Y.; Ishii, N.; Saeki, A.; Seki, S.; Tagawa, S.; Taniguchi, M.; Kawai, T.; Aida, T. Science 2006, 314, 1761-1764
84. Amaya, T.; Seki, S.; Moriuchi, T.; Nakamoto, K.; Nakata, T.; Sakane, H.; Saeki, A.; Tagawa, S.; Hirao, T. J. Am. Chem. Soc. 2009, 131, 408-409
85. Maeda, H.; Bando, Y.; Haketa, Y.; Honsho, Y.; Seki, S.; Nakajima, H.; Tohnai, N. Chem.-Eur. J. 2010, 16, 10994-11002
86. Sakurai, T.; Tashiro, K.; Honsho, Y.; Saeki, A.; Seki, S.; Osuka, A.; Muranaka, A.; Uchiyama, M.; Kim, J.; Ha, S.; Kato, K.; Takata, M.; Aida, T. J. Am. Chem. Soc. 2011, 133, 6537-6540
87. Li, W.-S.; Yamamoto, Y.; Fukushima, T.; Saeki, A.; Seki, S.; Tagawa, S.; Masunaga, H.; Sasaki, S.; Takata, M.; Aida, T. J. Am. Chem. Soc. 2008, 130, 8886-8887
88. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326
89. Altomare, A.; Burla, M.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119
90. CrystalStructure ver 3.8, Crystal Structure Analysis Package; Rigaku and Rigak Americas: The Woodlands, TX, 2000-2007.
91. Sheldrick, G. M. Acta Crystallogr., A 2008, 64, 112-122
92. Gaussian 03, Revision D.01; Frisch, M. J., Gaussian, Inc.: Wallingford, CT, 2004.
93. Scott, A. T.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513