Polymorphism in opto-electronic materials with a benzothiazole-fluorene core: A consequence of high conformational flexibility of π-conjugated backbone and alkyl side chains

Crystal Growth and Design

Volumn 11, Issue 5, 2011, Pages 1615-1622

  Dikundwar, Amol G ^a   Dutta, Gitish K ^a   Row, Tayur N Guru ^a   Patil, Satish ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL CHAIN; ALKYL SIDE CHAINS; CHARGE TRANSPORT PROPERTIES; CONFORMATIONAL FLEXIBILITY; CONJUGATED BACKBONES; FLUORENES; KEY FACTORS; OPTO-ELECTRONICS; ORGANIC SEMICONDUCTING MATERIALS; PHOTOPHYSICAL PROPERTIES; POLYMORPHIC MODIFICATIONS; SINGLE CRYSTAL X-RAY DIFFRACTION;

AROMATIC COMPOUNDS; OPTOELECTRONIC DEVICES; SINGLE CRYSTALS; TRANSPORT PROPERTIES; X RAY DIFFRACTION;

FLUORINE CONTAINING POLYMERS;

EID: 79957933493     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg101579f     Document Type: Article

References (47)

1. McCrone, W. C. In Physics and Chemistry of the Organic Solid State; Fox, D.; Labes, M. M.; Weissberger, A., Eds.; Wiley-Interscience: New York, 1965; Vol. 2, pp 725-767.
2. Threlfall, T. L. Analyst 1995, 120, 2435.
3. (a) Byrn, S. R Solid State Chemistry of Drugs; Academic Press: New York, 1982;
4. (b) Munshi, P.; Venugopala, K. N.; Jayashree, B. S.; Guru Row, T. N. Cryst. Growth. Des. 2004, 4, 1105.
5. Witte, G.; Woll, C. J. Mater. Res. 2004, 19, 1889.
6. (a) Biedermann, P. U.; Stezowski, J. J.; Agranat, I. Chem.-Eur. J. 2006, 12, 3345.
7. (b) Oana, D.; Jurchescu, O. D.; Mourey, D. A.; Subramanian, S.; Parkin, S. R.; Vogel, B. M.; Anthony, J. E.; Jackson, T. N.; Gundlach, D. J. Phys. Rev. B 2009, 80, 085201.
8. (c) Draxl, C. A.; Nabok, D.; Puschnig, P.; Meisenbichler, C. New. J. Phys. 2009, 11, 125010.
9. Troisi, A.; Orlandi, G. J. Phys. Chem. B 2005, 109, 1849.
10. (a) Mattheus, C. C.; Dros, A. B.; Baas, J.; Oostergetel, G. T.; Meetsma, A.; Boer, J. L. D.; Palstra, T. T. M. Syn. Met. 2003, 138, 475.
11. (b) Brillante, A.; Bilotti, I.; Valle, R G. D.; Venuti, E.; Masino, M.; Girlando, A Adv. Mater. 2005, 17, 2549.
12. (c) Tang, Q.; Zhang, D.; Wang, S.; Ke, N.; Xu, J.; Yu, J. C.; Miao, Q. Chem. Mater. 2009, 21, 1400.
13. Pfattner, R.; Torrent, M. M.; Bilotti, I.; Brillante, A.; Milita, S.; Liscio, F.; Biscarini, F.; Marszalek, T.; Ulanski, J.; Nosal, A.; Lipman, M. G.; Leufgen, M.; Schmidt, G.; Molenkamp, L. W.; Laukhin, V.; Veciana, J.; Rovira, C. Adv. Mater. 2010, 22, 4198.
14. (a) Tang, Q.; Zhang, D.; Wang, S.; Ke, N.; Xu, J.; Yu, J. C.; Miao, Q. Chem. Mater. 2009, 21, 1400.
15. (b) Brillante, A.; Bilotti, I.; Biscarini, F.; Valle, R G. D.; Venuti, E. Chem. Phys. 2006, 328, 125.
16. Ziegler, C. In Handbook of Organic Conductive Molecules and Polymers 3; Nalwa, H. S., Ed.; J. Wiley and Sons: Chichester, U. K., 1997; p 677.
17. Bernstein, J.; Davey, R J.; Henck, J. O. Angew. Chem., Int. Ed. 1999, 111, 3646;
18. Angew. Chem., Int. Ed. 1999, 38, 3440Concomitant polymorphs crystallize simultaneously from the same solvent and in the same crystallizing flask under identical crystal growth conditions.
19. Thallapally, P. K.; Jetti, R. K R.; Katz, A. K.; Carrell, H. L.; Singh, K.; Lahiri, K.; Kotha, S.; Boese, R.; Desiraju, G. R. Angew. Chem., Int. Ed. 2004, 43, 1149.
20. (a) Chyall, L. J.; Tower, J. M.; Coates, D. A.; Houston, T. L.; Childs, S. L. Cryst. Growth Des. 2002, 2, 505.
21. Hilden, J. L.; Reyes, C. E.; Kelm, M. J.; Tan, J. S.; Stowell, J. G.; Morris, K R. Cryst. Growth Des. 2003, 3, 921.
22. Childs, S. L.; Chyall, L. J.; Dunlap, J. T.; Coates, D. A.; Stahly, B. C.; Stahly, G. P. Cryst. Growth Des. 2004, 4, 441.
23. (b) Zaccaro, J.; Matic, J.; Myerson, A. S.; Garetz, B. A. Cryst. Growth Des. 2001, 1, 5.
24. (c) Trask, A. V.; Motherwell, W. D. S.; Jones, W. Chem. Commun. 2004, 890.
25. (d) Ha, J. M.; Wolf, J. H.; Hillmyer, M. A.; Ward, M. D. J. Am. Chem. Soc. 2004, 126, 3382.
26. (e) Lang, M.; Grzesiak, A L.; Matzger, A. J. J. Am. Chem. Soc. 2002, 124, 14834.
27. (f) Bonafede, S. J.; Ward, M. D. J. Am. Chem. Soc. 1995, 117, 7853.
28. Mitchell, C. A.; Yu, L.; Ward, M. D. J. Am. Chem. Soc. 2001, 123, 10830.
29. (g) Davey, R. J.; Blagden, N.; Potts, G. D.; Docherty, R J. Am. Chem. Soc. 1997, 119, 1767.
30. (a) Prasad, K R.; Chandrakumar, A.; Dikundwar, A G.; Guru Row, T. N. CrystEngComm 2010, 12, 3452.
31. (b) Chopra, D.; Nagarajan, K.; Guru Row, T. N. Cryst. Growth Des. 2005, 5, 1035.
32. Chopra, D.; Guru Row, T. N. Cryst. Growth Des. 2005, 5, 1679.
33. (c) Mahapatra, S.; Nayak, S. K.; Prathapa, S. J.; Guru Row, T. N. Cryst. Growth Des. 2008, 8, 1223.
34. Mahapatra, S.; Venugopala, K N.; Guru Row, T. N. Cryst. Growth Des. 2010, 10, 1866.
35. (d) Thakur, T. S.; Sathishkumar, R.; Dikundwar, A. G.; Guru Row, T. N.; Desiraju, G. R. Cryst. Growth Des. 2010, 10, 4246.
36. Sun, Y.; Duan, L.; Wei, P.; Qiao, J.; Dong, G.; Wang, L.; Qiu, Y. Org. Lett. 2009, 11, 2069.
37. Hung, M. C.; Liao, J. L.; Chen, S. A.; Chen, S. H.; Su, A. C. J. Am. Chem. Soc. 2005, 127, 14576.
38. Oxford Diffraction. CrysAlis PRO CCD and CrysAlis PRO RED; Oxford Diffraction Ltd.: Yarnton, England, 2009.
39. Oxford instruments, Cryojet XL/HT controller; Oxford Diffraction Ltd.: Yarnton, England.
40. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112.
41. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837.
42. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
43. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7.
44. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; Van de Streek, J. J. Appl. Crystallogr. 2006, 39, 453.
45. Dusek, M.; Petricek, V.; Wunschel, M.; Dinnebier, R. E.; van Smaalen, S. J. Appl. Crystallogr. 2001, 34, 398.
46. Jo, J.; Chi, C.; Hoger, S.; Wegner, G.; Yoon, D. Y. Chem.-Eur. J. 2004, 10, 2681.
47. Byun, H. Y.; Chung, I. J.; Shim, H. K.; Kim, C. Y. Chem. Phys. Lett. 2004, 393, 197.