Modification of Oligolactic Acid with Tetracarboxylic p-tert-Butylthiacalix[4]arene Derivatives: Effect of Macrocyclic Fragment Configuration on Aggregation and Thermal Properties of Copolyesters

Vladimir V. Gorbachuk,^а Olga A. Mostovaya,^а Vladimir G. Evtugyn,^b Yuri N. Osin,^b Ildar Kh. Rizvanov,^c Alexander V. Gerasimov,^а and Ivan I. Stoikov^а@

^аKazan Federal University, A.M. Butlerov Chemical Institute, 420008 Kazan, Russian Federation

^bInterdisciplinary Center for Analytical Microscopy of Kazan Federal University, 420008 Kazan, Russian Federation

^cA.E. Arbuzov Institute of Organic and Physical Chemistry of KSC RAS, 420088 Kazan, Russian Federation

^@Corresponding author E-mail: ivan.stoikov@mail.ru

DOI: 10.6060/mhc170513s

Macroheterocycles2017 10(2) 174-181

A novel approach to modification of oligolactic acid with three stereoisomers (cone, partial cone, 1,3-alternate) of p-tert-butylthiacalix[4]arene carboxylate derivatives has been developed. Using non-covalent self-assembly in dichloromethane, submicron spherical particles with 701 (cone), 362 (partial cone), 371 nm (1,3-alternate) size were obtained. Nanoprecipitation in the acetone-water mixture allowed forming particles of lower diameter, i.e. 191 (cone), 155 (partial cone) and 98 nm (1,3-alternate). It was shown by simultaneous thermogravimetry and differential scanning calorimetry that introduction of the macrocyclic fragments into the oligolactic acid increased its thermal stability. The temperature corresponding to the start of thermal decomposition was shifted from 246 °C (non-modified oligolactic acid) to 263 °C (that modified with macrocycles in partial cone and cone conformations) and 278 °C (derivative of 1,3-alternate).

References:

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1. Gao C., Wang Y., Zhu W., Shen Zh. Chin. J. Polym. Sci. 2014, 32, 1431−1441.
https://doi.org/10.1007/s10118-014-1528-4

2. Belali S., Reza Karimi A., Hadizadeh M. Polymer 2017, 109, 93−105.
https://doi.org/10.1016/j.polymer.2016.12.041

3. Wu R., Al-Azemi T.F., Bisht K.S. RSC Adv. 2014, 4, 16864–16870.
https://doi.org/10.1039/c3ra47678b

4. Garlotta D. Journal of Polymers and the Environment 2001, 9, 63.
https://doi.org/10.1023/A:1020200822435

5. Maeda H., Kasuga T. Acta Biomaterialia 2006, 2, 403–408.
https://doi.org/10.1016/j.actbio.2006.03.002

6. Chu C.R., Coutts R.D., Yoshioka M., Harwood F.L., Monosov A.Z., Amiel D. J. Biomed. Mater. Res. 1995, 29, 1147−1154.
https://doi.org/10.1002/jbm.820290915

7. Félix Lanao R.P., Leeuwenburgh S.C.G., Wolke J.G.C., Jansen J.A. Biomaterials 2011, 32, 8839−8847.
https://doi.org/10.1016/j.biomaterials.2011.08.005

8. Mehanny M., Hathout R.M., Geneidi A.S., Mansour S. J. Biomed. Mater. Res. Part A 2017, 105A, 1433–1445.
https://doi.org/10.1002/jbm.a.36028

9. Shen J., Hao A., Du G., Zhang H., Sun H. Carbohydr. Res. 2008, 343, 2517–2522.
https://doi.org/10.1016/j.carres.2008.06.010

10. Morohashi N., Narumi F., Iki N., Hattori T., Miyano S. Chem. Rev. 2006, 106, 5291−5316.
https://doi.org/10.1021/cr050565j

11. Kumar R., Lee Y.O., Bhalla V., Kumar M., Kim J.S. Chem. Soc. Rev. 2014, 43, 4824−4870.
https://doi.org/10.1039/c4cs00068d

12. Vavilova A.A., Nosov R.V., Mostovaya O.A., Stoikov I.I. Macroheterocycles 2016, 9, 294−300.
https://doi.org/10.6060/mhc160531s

13. Puplampu J.B., Yakimova L.S., Vavilova A.A., Rizvanov I.K., Stoikov I.I. Macroheterocycles 2015, 8, 75−80.
https://doi.org/10.6060/mhc140722s

14. Mostovaya O.A., Agafonova M.N., Galukhin A.V., Khayrutdinov B.I., Islamov D., Kataeva O.N., Antipin I.S., Konovalov A.I., Stoikov I.I. J. Phys. Org. Chem. 2014, 27, 57−65.
https://doi.org/10.1002/poc.3236

15. Trush V.V., Kharchenko S.G., Tanchuk V.Y., Kalchenko V.I., Vovk A.I. Org. Biomol. Chem. 2015, 13, 8803−8806.
https://doi.org/10.1039/C5OB01247C

16. Padnya P.L., Andreyko E.A., Mostovaya O.A., Rizvanov I.Kh., Stoikov I.I. Org. Biomol. Chem. 2015, 13, 5894−5904.
https://doi.org/10.1039/C5OB00548E

17. Nosov R.V., Stoikov I.I. Macroheterocycles 2015, 8, 120−127.
https://doi.org/10.6060/mhc140929s

18. Nosov R.V., Stoikov I.I. Macroheterocycles 2014, 7, 345−350.
https://doi.org/10.6060/mhc140720s

19. Stoikov I.I., Mostovaya O.A., Yakimova L.S., Yantemirova A.A., Antipin I.S., Konovalov A.I. Mendeleev Commun. 2010, 20, 359–360.
https://doi.org/10.1016/j.mencom.2010.11.021

20. Khomich E., Kashapov M., Vatsouro I., Shokova E., Kovalev V. Org. Biomol. Chem. 2006, 4, 1555−1560.
https://doi.org/10.1039/b601709f

21. Gorbatchuk V.V., Porfireva A.V., Stepanova V.B., Kuzin Yu.I., Evtugyn V.G., Shamagsumova R.V., Stoikov I.I., Evtugyn G.A. Sens. Actuators, B 2017, 246, 136−145.
https://doi.org/10.1016/j.snb.2017.02.061

22. Harshe Y.M., Storti G., Morbidelli M., Gelosa S., Moscatelli D. Macromolecular Reaction Engineering 2007, 1, 611−621.
https://doi.org/10.1002/mren.200700019

23. Perego G., Cella G.D., Bastioli C. J. Appl. Polym. Sci. 1996, 59, 37−43.
https://doi.org/10.1002/(SICI)1097-4628(19960103)59:1<37::AID-APP6>3.0.CO;2-N

24. Mittal G., Sahana D.K., Bhardwaj V., Kumar M.R. J. Controlled Release 2007, 119, 77−85.
https://doi.org/10.1016/j.jconrel.2007.01.016

25. Yushkova E.A., Stoikov I.I. Langmuir 2009, 25, 4919−4928.
https://doi.org/10.1021/la8040902

26. Fessi H., Puisieux F., Devissaguet J.Ph., Ammoury N., Benita S. Int. J. Pharm. 1989, 55, R1−R4.
https://doi.org/10.1016/0378-5173(89)90281-0

27. Morales-Cruz M., Flores-Fernández G.M., Morales-Cruz M., Orellano E.A., Rodriguez-Martinez J.A., Ruiz M., Griebenow K. Results in Pharma Sciences 2012, 2, 79–85.
https://doi.org/10.1016/j.rinphs.2012.11.001

28. Chen Y., Yang Y., Su J., Tan L., Wang Y. React. Funct. Polym. 2007, 67, 396–407.
https://doi.org/10.1016/j.reactfunctpolym.2007.02.011

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Modification of Oligolactic Acid with Tetracarboxylic p-tert-Butylthiacalix[4]arene Derivatives: Effect of Macrocyclic Fragment Configuration on Aggregation and Thermal Properties of Copolyesters

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