Selective crystal growth of the anhydrous and monohydrate forms of theophylline on self-assembled monolayers

Angewandte Chemie - International Edition

Volumn 46, Issue 12, 2007, Pages 1988-1991

  Cox, Jason R ^a   Dabros, Marta ^a   Shaffer, Jeanne A ^a   Thalladi, Venkat R ^a  

^a Life Science and Bioengineering Center   (United States)

Author keywords

Crystal growth; Epitaxy; Hydrogen bonds; Polymorphism; Self assembled monolayers

Indexed keywords

CRYSTAL GROWTH; CRYSTALLIZATION; EPITAXIAL GROWTH; ETHANOL; HYDROGEN BONDS; HYDROPHILICITY; POLYMORPHISM;

ANHYDROUS; GEOMETRIC EPITAXY; HYDROPHILIC THIOL; THEOPHYLLINE;

SELF ASSEMBLED MONOLAYERS;

BRONCHODILATING AGENT; THEOPHYLLINE; THIOL DERIVATIVE;

ARTICLE; CHEMISTRY; CRYSTALLIZATION; POWDER DIFFRACTION; SOLUBILITY; SURFACE PROPERTY; X RAY DIFFRACTION;

BRONCHODILATOR AGENTS; CRYSTALLIZATION; POWDER DIFFRACTION; SOLUBILITY; SULFHYDRYL COMPOUNDS; SURFACE PROPERTIES; THEOPHYLLINE; X-RAY DIFFRACTION;

EID: 34247577262     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604674     Document Type: Article

References (49)

1. S. R. Byrn, R. R. Pfeiffer, J. G. Stowell, Solid-State Chemistry of Drugs, 2nd ed., SSCI, West Lafayette, 1999;
2. Polymorphism in Pharmaceutical Solids (Ed.: H. G. Brittain), Marcel Dekker, New York, 1999;
3. J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press, New York, 2002;
4. Polymorph ism in the Pharmaceutical Industry (Ed.: R. Hilfiker), Wiley-VCH, Weinheim, 2006.
5. S. R. Chemburkar, J. Bauer, K. Deming, H. Spiwek, K. Patel, J. Morris, R. Henry, S. Spanton, W. Dziki, W. Porter, J. Quick, P. Bauer, J. Donaubauer, B. A. Narayanan, M. Soldani, D. Riley, K. McFarland, Org. Process Res. Dev. 2000, 4, 413-417.
6. C. Näther, I. Jess, Angew. Chem. 2006, 118, 6529-6531;
7. Angew. Chem. Int. Ed. 2006, 45, 6381-6383.
8. For a recent discussion on the use of the terms polymorphism and pseudopolymorphism, see: G. R. Desiraju, CrystEngComm 2003, 5, 466-467;
9. K. R. Seddon, Cryst. Growth Des. 2004, 4, 1087;
10. G. R. Desiraju, Cryst. Growth Des. 2004, 4, 1089-1090;
11. J. Bernstein, Cryst. Growth Des. 2005, 5, 1661-1662;
12. A. Nangia, Cryst. Growth Des. 2006, 6, 2-4.
13. Recently, this classical approach has been automated into a high-throughput method. See, for example: S. L. Morissette, S. Soukasene, D. Levinson, M. J. Cima, O. Almarsson, Proc. Natl. Acad. Set USA 2003, 100, 2180-2184.
14. J. W. Mullin, Crystallization, 4th ed., Butterworth-Heinemann, New York, 2001.
15. M. Lahav, L. Addadi, L. Leiserowitz, Proc. Natl. Acad. Sci. USA 1987, 84, 4737-4738.
16. E. M. Landau, M. Levanon, L. Leiserowitz, M. Lahav, J. Sagiv, Nature 1985, 318, 353-356;
17. B. R. Heywood, S. Mann, Adv. Mater. 1994, 6, 9-20;
18. L. M. Frostman, M. D. Ward, Langmuir 1997, 13, 330-337.
19. L. M. Frostman, M. M. Bader, M. D. Ward, Langmuir 1994, 10, 576-582;
20. F. C. Meldrum, J. Flath, W. Knoll, Langmuir 1997, 13, 2033-2049;
21. J. Küther, R. Seshadri, W. Knoll, W. Tremel, J. Mater. Chem. 1998, 8, 641-650;
22. J. Aizenberg, A. J. Black, G. M. Whitesides, J. Am. Chem. Soc. 1999, 121, 4500-4509;
23. A. Y. Lee, A. Ulman, A. S. Myerson, Langmuir 2002, 18, 5886-5898;
24. N. Banno, T. Nakanishi, M. Matsunaga, T. Asahi, T. Osaka, J. Am. Chem. Soc. 2004, 126, 428-429;
25. R. Hiremath, S. W. Varney, J. A. Swift, Chem. Commun. 2004, 2676-2677;
26. R. Hiremath, J. A. Basile, S. W. Varney, J. A. Swift, J. Am. Chem. Soc. 2005, 127, 18321-18327.
27. P. W. Carter, M. D. Ward, J. Am. Chem. Soc. 1994, 116, 769-770.
28. C. A. Mitchell, L. Yu, M. D. Ward, J. Am. Chem. Soc. 2001, 123, 10830-10839;
29. C. Cashell, D. Corcoran, B. K. Hodnett, Chem. Commun. 2003, 374-375;
30. L. Yu, J. Am. Chem. Soc. 2003, 125, 6380-6381.
31. C. P. Price, A. L. Grzesiak, A. J. Matzger, J. Am. Chem. Soc. 2005, 127, 5512-5517.
32. Other methods to control polymorphism include the use of tailor-made auxiliaries, laser-induced nucleation, and crystallization in confined spaces. See: I. Weissbuch, L. Leisorowitz, M. Lahav, Adv. Mater. 1994, 6, 952-956;
33. R. J. Davey, N. Blagden, G. D. Potts, R. Docherty, J. Am. Chem. Soc. 1997, 119, 1767-1772;
34. J. Zaccaro, J. Matic, A. S. Myerson, B. A. Garetz, Cryst. Growth Des. 2001, 1, 5-8;
35. L. J. Chyall, J. M. Tower, D. A. Coates, T. L. Houston, S. L. Childs, Cryst. Growth Des. 2002, 2, 505-510;
36. J. L. Hilden, C. E. Reyes, M. J. Kelm, J. S. Tan, J. G. Stowell, K. R. Morris, Cryst. Growth Des. 2003, 3, 921-926;
37. J.-M. Ha, J. H. Wolf, M. A. Hillmyer, M. D. Ward, J. Am. Chem. Soc. 2004, 126, 3382-3383.
38. D. J. Sutor, Acta Crystallogr. 1956, 9, 969-970;
39. A. A. Naqvi, G. C. Bhattacharyya, J. Appl. Crystallogr. J. Appl. Cryst. 1981, 14, 464.
40. J. Bernstein, R. J. Davey, J.-O. Henck, Angew. Chem. 1999, 111, 3646-3669;
41. Angew. Chem. Int. Ed. 1999, 38, 3440-3461.
42. N. V. Phadnis, R. Suryanarayanan, J. Pharm. Sci. 1997, 86, 1256-1263.
43. A. Ulman, Chem. Rev. 1996, 96, 1533-1554;
44. J. C. Love, L. A. Estroff, J. K. Kriebel, R. G. Nuzzo, G. M. Whitesides, Chem. Rev. 2005, 105, 1103-1169.
45. Initial results were obtained from experiments performed under the high-humidity conditions (60-80% relative humidity) that are common in the summer in Worcester. We repeated the experiments under controlled-humidity conditions to verify the reproducibility of the results. Similar results were obtained when crystallizations were carried out in 95% ethanol solutions under low-humidity conditions (25% relative humidity).
46. Glass slides with exposed silanol (SiOH) groups were prepared by treating freshly cut slides with an air plasma (in an SPI-III plasma etcher) for 45 s. These slides are similar to SAM-3, SAM-4, and SAM-5 in terms of their hydrophilicity and hydrogen bonding. They, however, lack the long-range two-dimensional order and periodicity that are characteristic of the SAMs.
47. A. C. Hillier, M. D. Ward, Phys. Rev. B 1996, 54, 14037-14051;
48. J. A. Last, D. E. Hooks, A. C. Hillier, M. D. Ward, J. Phys. Chem. B 1999, 103, 6723-6733.
49. [17] The epitaxy calculations assume that templated nucleation occurs on these domains.