Direct evidence of a liquid-crystalline phase induced by intermolecular C-H⋯Cl interactions on the basis of ir spectroscopy and theoretical simulations

Chemistry - A European Journal

Volumn 17, Issue 1, 2011, Pages 111-116

  Lai, Long Li ^a   Yang, Chun Ming ^a   Liu, Chia Chun ^a   Cheng, Kung Lung ^b   Wen, Yu Shen ^c   Hung, Chen Hsiung ^c   Luo, Tzuoo Tsair ^c   Kuo, Ming Yu ^a  

^a NATIONAL CHI NAN UNIVERSITY   (Taiwan)

^b Industrial Research Nstitute   (Taiwan)

^c INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

Cl H interactions; dyes pigments; hydrogen bonding; liquid crystals; molecular dynamics

Indexed keywords

ALKYL CHAIN; DYES/PIGMENTS; FLEXIBLE ALKYL CHAINS; HYDROGEN BONDING; IR SPECTROSCOPY; LIQUID-CRYSTALLINE PHASE; MESOGENICS; THEORETICAL SIMULATION; THERMAL PROCESS;

ALKYLATION; CRYSTALS; HYDROGEN; LIQUID CRYSTALS; MOLECULAR DYNAMICS;

HYDROGEN BONDS;

AZO COMPOUND; CHLORINATED HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; HYDROGEN BOND; INFRARED SPECTROPHOTOMETRY; LIQUID CRYSTAL; METHODOLOGY; SYNTHESIS; THEORETICAL MODEL; X RAY CRYSTALLOGRAPHY;

AZO COMPOUNDS; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; HYDROCARBONS, CHLORINATED; HYDROGEN BONDING; LIQUID CRYSTALS; MODELS, THEORETICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY, INFRARED;

EID: 78650966556     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002177     Document Type: Article

References (49)

1. G. R. Desiraju, T. Steiner, in The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999
2. G. R. Desiraju, Acc. Chem. Res. 2002, 35, 565
3. L. L. Lai, C.-H. Wu, K.-L. Lu, Y.-S. Wen, Y.-H. Liu, Y. Wang, K.-L. Cheng, D. V. Soldatov, Z. Yu, K. Yu, CrystEngComm 2007, 9, 345.
4. R. Taylor, O. Kennard, J. Am. Chem. Soc. 1982, 104, 5063
5. L. Brammer, E. A. Bruton, P. Sherwood, Cryst. Growth Des. 2001, 1, 277
6. V. R. Thalladi, H.-C. Weiss, D. Bläser, R. Boese, A. Nangia, G. R. Desiraju, J. Am. Chem. Soc. 1998, 120, 8702
7. P. B. Hitchcock, K. R. Seddon, T. Welton, J. Chem. Soc. Dalton Trans. 1993, 2639.
8. C. M. Paleos, D. Tsiourvas, Liquid crystals 2001, 28, 1127 and references therein
9. C. M. Paleos, D. Tsiourvas, Angew. Chem. 1995, 107, 1839
10. Angew. Chem. Int. Ed. Engl. 1995, 34, 1696 and references therein.
11. C.-Y. Lin, L.-J. Lee, C.-L. Lin, P.-H. Lin, L.-L. Lai, Y.-S. Wen, J. Chin. Chem. Soc. 2007, 54, 693
12. A. Kohlmeier, D. Janietz, Chem. Mater. 2006, 18, 59
13. E. J. Foster, C. Lavigueur, Y. C. Ke, V. E. Williams, J. Mater. Chem. 2005, 15, 4062
14. D. Goldmann, D. Janietz, C. Schmidt, J. H. Wendroff, J. Mater. Chem. 2004, 14, 1521.
15. T. Kato, J. M. J. Fréchet, J. Am. Chem. Soc. 1989, 111, 8533
16. T. Kato, H. Kihara, U. Kumar, T. Uryu, J. M. J. Fréchet, Angew. Chem. 1994, 106, 1728
17. Angew. Chem. Int. Ed. Engl. 1994, 33, 1644.
18. L. Schmidt-Mende, A. Fechtenkotter, K. Müllen, E. Moons, R. H. Friend, J. D. MacKenzie, Science 2001, 293, 1119
19. A. M. Van de Craats, N. Stutzmann, O. Bunk, M. M. Nielsen, M. Watson, K. Müllen, H. D. Chanzy, H. Sirringhaus, R. H. Friend, Adv. Mater. 2003, 15, 495
20. A. M. Van de Craats, J. M. Warman, A. Fechtenkoetter, J. D. Brand, M. A. Harbison, K. Müllen, Adv. Mater. 1999, 11, 1469.
21. E. J. Foster, R. B. Jones, C. Lavigueur, V. E. Williams, J. Am. Chem. Soc. 2006, 128, 8569
22. T. H. Chang, B. R. Wu, M. Y. Chiang, S. C. Liao, C. W. Ong, H. F. Hsu, S. Y. Lin, Org. Lett. 2005, 7, 4075
23. M. D. McKenna, J. Barbera, M. Marcos, J. L. Serrano, J. Am. Chem. Soc. 2005, 127, 619
24. E. J. Foster, J. Babuin, N. Nguyen, V. E. Williams, Chem. Commun. 2004, 2052
25. B. L. Feringa, R. A. Van Delden, N. Koumura, E. M. Geertsema, Chem. Rev. 2000, 100, 1789.
26. H. L. Nguyen, P. N. Horton, M. B. Hursthouse, A. C. Legon, D. W. Bruce, J. Am. Chem. Soc. 2004, 126, 16
27. P. Metrangolo, C. Präsang, G. Resnati, R. Liantonio, A. C. Whitwood, D. W. Bruce, Chem. Commun. 2006, 3290
28. D. W. Bruce, P. Metrangolo, F. Meyer, C. Präsang, G. Resnati, G. Terraneo, A. C. Whitwood, New. J. Chem. 2008, 32, 477
29. J. Xu, X. Liu, T. Lin, J. Huang, C. He, Macromolecules 2005, 38, 3554
30. J. Xu, X. Liu, J. K.-P. Ng, T. Lin, C. He, J. Mater. Chem. 2006, 16, 3540.
31. A. Grafe, D. Janietz, T. Frese, J. H. Wendroff, Chem. Mater. 2005, 17, 4979
32. D. Goldmann, D. Janietz, C. Schmidt, J. H. Wendroff, Angew. Chem. 2000, 112, 1922
33. Angew. Chem. Int. Ed. 2000, 39, 1851.
34. J. D. Martin, C. Keary, T. A. Thornton, M. P. Novotnak, J. W. Knutson, J. C. Folmer, Nature 2006, 5, 271
35. F. Neve, O. Francescangeli, A. Crispini, Inorg. Chim. Acta 2002, 338, 51.
36. L.-L. Lai, E. Wang, Helv. Chim. Acta 2001, 84, 3581
37. L.-L. Lai, L.-J. Lee, G.-H. Lee, Y. Wang, K.-L. Lu, S.-J. Lee, Liquid Crystals 2001, 28, 1513.
38. L. R. MacGillivray, J. L. Reid, J. A. Ripmeester, J. Am. Chem. Soc. 2000, 122, 7817.
39. 3) in Figure 2 b is 3.005.
40. A. Bondi, J. Phys. Chem. 1964, 68, 441.
41. The corresponding C-H⋯O angles are 140.34, 144.87 and167.50°, respectively.
42. All of thermal annealing and molecular dynamics (MD) simulations were carried out in the canonical (NVT) ensemble with PCFF force field by Accelrys Materials Studio, version 4.2, Accelrys Inc, San Diego, CA, 2006.
43. J. R. Maple, U. Dinur, A. T. Hagler, Proc. Natl. Acad. Sci. USA 1988, 85, 5350
44. J. R. Maple, M. J. Hwang, T. P. Stockfisch, U. Dinur, M. Waldman, C. S. Ewig, A. T. Hagler, J. Comput. Chem. 1994, 15, 162
45. J. R. Maple, M. J. Hwang, T. P. Stockfisch, A. T. Hagler, Isr. J. Chem. 1994, 34, 195
46. H. Sun, Macromolecules 1995, 28, 701
47. H. Sun, S. J. Mumby, J. R. Maple, A. T. Hagler, J. Am. Chem. Soc. 1994, 116, 2978.
48. G. Socrates, in Infrared and Raman Characteristic Group Frequencies 3rd Ed., Wiley, UK, 2001, pp. 207
49. E. F. Mooney, Spectrochim. Acta. 1964, 20, 1021.