- Aluminum siloxide,
- Catalyst,
- Lactide,
- Stereoselective,
- Polymerization
Copyright (c) 2017 Yu Zhang, Xuan Pang, Lili Ma, Zhaohui Tang
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
Abstract
Stereoselective polymerization of lactide is receiving growing attention in polymer science. Herein, a five-coordinate aluminum siloxide complex, [2,2-dimethyl- 1,3-propylenebis(3,5-di-tert- butylsalicylideneiminato)] (triphenyl-silanolato) aluminium (III) (1), was prepared from AlEt3, N,N´-(2,2-dimethylpropylene) bis(3,5-di-tert-butylsalicylideneimine) and triphenyl-silanol. X-ray analysis demonstrated that 1 contained a five-coordinate aluminum atom with distorted trigonal bipyramidal geometry in the solid state. 1H NMR and 13C NMR spectra indicated that the two conformational stereoisomers of 1 tautomerizes rapidly in chloroform or toluene solution at room temperature. 1 showed high stereoselectivity (Pm = 0.84) for the ROP of rac-lactide in toluene at 100°C, and polymerized rac-lactide to crystalline polymer (Tm = 178°C). This is the first report of stereoselective polymerization of rac-lactide using aluminum siloxide as a catalyst.
References
- Pang, X., Zhuang, X., Tang, Z.,Chen, X., Biotechnol. J. 5, 1125 (2010).
- Sinha Ray, S., Acc. Chem. Res. 45, 1710 (2012).
- Pilone, A., Press, K., Goldberg, I., Kol, M., Mazzeo, M.,Lamberti, M., J. Am. Chem. Soc. 136, 2940 (2014).
- Song, W., Tang, Z., Lei, T., Wen, X., Wang, G., Zhang, D., Deng, M., Tang, X.,Chen, X., Nanomed. Nanotechnol. Biol. Med. 12, 377 (2016).
- Bruna, J. E., Quilodran, H., Guarda, A., Rodriguez, F., Galotto, M. J., Figueroa, P., J. Chil. Chem. Soc. 60, 3009 (2015).
- Zhang, X., Mattheus, Goosen, F., Wyss, S.,Pichora, D., J. Macromol. Sci. Polymer Rev. 33, 81 (1993).
- Shao, J., Sun, J., Bian, X., Cui, Y., Zhou, Y., Li, G.,Chen, X., Macromolecules 46, 6963 (2013).
- Tsuji, H., Horii, F., Hyon, S. H.,Ikada, Y., Macromolecules 24, 2719 (1991).
- Sun, J., Shao, J., Huang, S., Zhang, B., Li, G., Wang, X.,Chen, X., Materials Letters 89, 169 (2012).
- Honrado, M., Otero, A., Fernández-Baeza, J., Sánchez-Barba, L. F., Garcés, A. s., Lara-Sánchez, A. n.,Rodrı́guez, A. M., Organometallics 33, 1859 (2014).
- Kazakov, O. I., Datta, P. P., Isajani, M., Kiesewetter, E. T.,Kiesewetter, M. K., Macromolecules 47, (2014).
- Fliedel, C., Vila‐Viçosa, D., Calhorda, M. J., Dagorne, S.,Avilés, T., ChemCatChem 6, 1357 (2014).
- Sauer, A., Kapelski, A., Fliedel, C., Dagorne, S., Kol, M.,Okuda, J., Dalton Trans. 42, 9007 (2013).
- Liu, B., Roisnel, T., Guégan, J. P., Carpentier, J. F. o.,Sarazin, Y., Chem. Eur. J. 18, 6289 (2012).
- Sarazin, Y., Liu, B., Roisnel, T., Maron, L.,Carpentier, J. F., J. Am. Chem. Soc. 133, 9069 (2011).
- Sutar, A. K., Maharana, T., Dutta, S., Chen, C. T.,Lin, C. C., Chem. Soc. Rev. 39, 1724 (2010).
- Jones, M. D., Brady, L., McKeown, P., Buchard, A., Schäfer, P. M., Thomas, L. H., Mahon, M. F., Woodman, T. J.,Lowe, J. P., Chem. Sci. 6, 5034 (2015).
- Aluthge, D., Ahn, J.,Mehrkhodavandi, P., Chem. Sci. 6, 5284 (2015).
- Sun, Z., Duan, R., Yang, J., Zhang, H., Li, S., Pang, X., Chen, W.,Chen, X., RSC Adv. 6, 17531 (2016).
- Spassky, N., Wisniewski, M., Pluta, C.,Le Borgne, A., Macromol. Chem. Phys. 197, 2627 (1996).
- Yu, I., Acosta-Ramírez, A.,Mehrkhodavandi, P., J. Am. Chem. Soc. 134, 12758 (2012).
- Thomas, C. M., Chem. Soc. Rev. 39, 165 (2010).
- Bakewell, C., White, A. J., Long, N. J.,Williams, C. K., Angew. Chem. Int. Ed. Engl. 53, 9226 (2014).
- Darensbourg, D. J.,Karroonnirun, O., Organometallics 29, 5627 (2010).
- Du, H., Velders, A. H., Dijkstra, P. J., Zhong, Z., Chen, X.,Feijen, J., Macromolecules 42, 1058 (2009).
- Nomura, N., Chemistry 13, 4433 (2007).
- Nomura, N., Akita, A., Ishii, R.,Mizuno, M., J. Am. Chem. Soc. 132, 1750 (2010).
- Pang, X., Duan, R., Li, X., Gao, B., Sun, Z., Wang, X.,Chen, X., RSC Adv. 4, 22561 (2014).
- Press, K., Goldberg, I.,Kol, M., Angew. Chem. Int. Ed. Engl. 54, 14858 (2015).
- Pang, X., Duan, R., Li, X.,Chen, X., Polym. Chem. 5, 3894 (2014).
- Tang, Z., Chen, X., Pang, X., Yang, Y., Zhang, X.,Jing, X., Biomacromolecules 5, 965 (2004).
- Chamberlain, B. M., Cheng, M., Moore, D. R., Ovitt, T. M., Lobkovsky, E. B.,Coates, G. W., J. Am. Chem. Soc. 123, 3229 (2001).
- Atwood, D. A., Hill, M. S., Jegier, J. A.,Rutherford, D., Organometallics 16, 2659 (1997).
- Munoz-Hernandez, M. A., Keizer, T. S., Wei, P., Parkin, S.,Atwood, D. A., Inorg. Chem. 40, 6782 (2001).
- Tabthong, S., Nanok, T., Kongsaeree, P., Prabpai, S.,Hormnirun, P., Dalton Trans. 43, 1348 (2014).
- Addison, A. W., Rao, T. N., Reedijk, J., Rijn, J. v.,Verschoor, G. C., J. Chem. Soc., Dalton Trans. 7, 1349 (1984).
- Tang, Z. H., Chen, X. S., Yang, Y. K., Pang, X., Sun, J. R., Zhang, X. F.,Jing, X. B., J. Polym. Sci. A Polym. Chem. 42, 5974 (2004).
- Tang, Z., Pang, X., Sun, J., Du, H.,Chen, X., J. Polym. Sci. A Polym. Chem. 44, 4932 (2006).
- Tang, Z. H., Yang, Y. K., Pang, X., Hu, J. L., Chen, X. S., Hu, N. H.,Jing, X. B., J. Appl. Polym. Sci. 98, 102 (2005).
- Tang, Z. H., Chen, X. S., Pang, X., Yang, Y. K., Zhang, X. F.,Jing, X. B., Biomacromolecules 5, 965 (2004).