Liquid Silyl Derivative of beta-Cyclodextrin

Askar K. Gatiatulin,^a@ Marat A. Ziganshin,^a Galina I. Kurochkina,^b Artem V. Popkov,^b Mikhail K. Grachev,^b and Valery V. Gorbatchuk^a

^aA.M. Butlerov Institute of Chemistry, Kazan Federal University, 420008 Kazan, Russia

^bInstitute of Biology and Chemistry, Moscow State Pedagogical University, 119021 Moscow, Russia

^@Corresponding author E-mail: agatiatu@kpfu.ru

DOI: 10.6060/mhc170520g

Macroheterocycles 2017 10(2) 233-237

Per-6-О-(tert-butyl)(diphenyl)silyl-β-cyclodextrin was found to form metastable liquid phase, which is unusual for cyclodextrin mono-derivatives under ambient conditions. Also, it can exist in a solid amorphous state as a stable molecular glass. Conditions and parameters of phase transitions between crystal, glassy and liquid forms were determined. The studied compound is soluble in various solvents. Crystallization from its solutions and overcooled melt results in formation of two different polymorphs. The liquid mono-derivative of beta-cyclodextrin is amphiphilic and preferable for application in solutions, in pure form or even as a solvent for substrates with various structures.

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1. József S. Chem. Rev. 1998, 98, 1743–1754.
https://doi.org/10.1021/cr970022c

2. Asahara H., Kida T., Iwamoto T., Hinoue T., Akashi M. Tetrahedron 2014, 70, 197–203.
https://doi.org/10.1016/j.tet.2013.11.097

3. Kida T., Iwamoto T., Asahara H., Hinoue T., Akashi M. J. Am. Chem. Soc. 2013, 135(9), 3371–3374.
https://doi.org/10.1021/ja312367k

4. Blum W., Aichholz R. J. High. Resolut. Chromatogr. 1990, 13, 515–518.
https://doi.org/10.1002/jhrc.1240130716

5. Maas B., Dietrich A., Karl V., Kaunzinger A., Lemann D., Köpke T., Mosandl A. J. Microcolumn Sep. 1993, 5, 421–427.
https://doi.org/10.1002/mcs.1220050505

6. Khan A. R., Forgo P., Stine K. J., D'Souza V. T. Chem. Rev. 1998, 98, 1977–1996.
https://doi.org/10.1021/cr970012b

7. Uekama K., Hirayama F., Irie T. Chem. Rev. 1998, 98, 2045–2076.
https://doi.org/10.1021/cr970025p

8. Marrucho I. M., Branco L. C., Rebelo L. P. N. Annu. Rev. Chem. Biomol. Eng. 2014, 5, 527–546.
https://doi.org/10.1146/annurev-chembioeng-060713-040024

9. Hadgraft J., Lane M. E. Expert Opin. Drug. Deliv. 2016, 13(6), 1–35.
https://doi.org/10.1517/17425247.2016.1140146

10. Li W.-Y., Jin H. L., Armstrong D. W. J. Chromatogr. 1990, 509, 303–324.
https://doi.org/10.1016/S0021-9673(01)93089-4

11. Armstrong D. W., Li W., Chang C.-D. Anal. Chem. 1990, 62(9), 914–923.
https://doi.org/10.1021/ac00208a006

12. Memişoğlu E., Bochot A., Şen M., Charon D., Duchêne D., Hıncal A. A. J. Pharm. Sci. 2002, 91(5), 1214–1224.
https://doi.org/10.1002/jps.10105

13. Phama T. P. T., Choa C.-W., Yun Y.-S. Water Research 2010, 44(2), 352–372.
https://doi.org/10.1016/j.watres.2009.09.030

14. Zhao Y., Zhao J., Huang Y., Zhou Q., Zhang X., Zhang S. J. Hazard. Mater. 2014, 278, 320–329.
https://doi.org/10.1016/j.jhazmat.2014.06.018

15. Bettinetti G., Novák Cs., Sorrenti M. J. Therm. Anal. Calorim. 2002, 517–529.
https://doi.org/10.1023/A:1016043920156

16. Veiga M. D., Merino M., Fernández D., Lozano R. J. Therm. Anal. Calorim. 2002, 68, 511–516.
https://doi.org/10.1023/A:1016091803317

17. Kurochkina G. I., Popkov A. V., Levina I. I., Grachev M. K. Russ. J. Gen. Chem. 2016, 86, 317–320.
https://doi.org/10.1134/S1070363216020195

18. Yakimova L. S., Ziganshin M. A., Sidorov V. A., Kovalev V. V., Shokova E. A., Tafeenko V. A., Gorbatchuk V. V. J. Phys. Chem. B 2008, 112, 15569–15575.
https://doi.org/10.1021/jp804277u

19. Ziganshin M. A., Bikmukhametova A. A., Gerasimov A. V., Gorbatchuk V. V., Ziganshina S. A., Bukharaev A. A. Prot. Met. Phys. Chem. Surf. 2014, 50, 49–54.
https://doi.org/10.1134/S2070205114010171

20. Gataullina K. V., Ziganshin M. A., Stoikov I. I., Gubaidullin A. T., Gorbatchuk V. V. Phys. Chem. Chem. Phys. 2015, 17, 15887–15895.
https://doi.org/10.1039/C5CP02042E

21. Ashram M., Al-Ghezawi N., Awaad I. A., Asman G. Turk. J. Chem. 2009, 33, 647–656.
https://doi.org/10.3906/kim-0811-28

22. Gatiatulin A. K., Ziganshin M. A., Yumaeva G. F., Gubaidullin A. T., Suwinska K., Gorbatchuk V. V. RSC Adv. 2016, 6, 61984–61995.
https://doi.org/10.1039/C6RA11378H

23. Szejtli J. J. Mater. Chem. 1997, 7(4), 575–587.
https://doi.org/10.1039/a605235e

24. Ling C.-C., Darcy R., Risse W. J. Chem. Soc., Chem. Commun. 1993, 438–440.
https://doi.org/10.1039/C39930000438

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