Chinese Journal of Organic Chemistry >
A Study on Synthesis of Janus Heterofunctional Cubic Silsesquioxanes
Received date: 2016-08-31
Revised date: 2016-11-22
Online published: 2016-12-02
Supported by
Project supported by the National Natural Science Foundation of China (No. 21174162), the Province Natural Science Fund of Guangdong Province (No. 2016A030313162) and the Guangzhou Science and Technology Plan Projects (No. 201505051006333).
Design and synthesis of well-defined hetero-functional cubic silsesquioxane remain as international research focuses and challenges. In this work, we demonstrated in detail the synthesis of two Janus hetero-functional cubic silsesquioxane. We applied similar "bottom-up" method to construct the aimed Janus HFCSQ, which was carried out by using cyclic tetrasiloxanes as synthetic platforms and followed by further hydrolysis and cage-closure. The obtained products exhibited good solubility in THF, CHCl3 and DMSO, which embodied themselves potential use in further derivations and processing. The precise structure of these obtained Janus HFCSQ were fully characterized by FTIR, 1H NMR, Maldi-tof MS, 29Si NMR, WAXD and TGA. Red-shifts observed from Photoluminescence UV-vis analysis further confirmed extended conjugation of the silsesquioxane cages, which in turn proved the formation of completed cages.This work provided us a versatile novel method to prepare the resulting Janus HFCSQs, which can widely expand the species of silsesquioxane monomers and applications as well.
Peng Jun , Xing Yuxiu , Xu Kai . A Study on Synthesis of Janus Heterofunctional Cubic Silsesquioxanes[J]. Chinese Journal of Organic Chemistry, 2017 , 37(3) : 636 -645 . DOI: 10.6023/cjoc201608032
[1] (a) Dickson, W.; Beckett, S.; McClatchey, C.; Murphy, A.; O'Connor, D.; Wurtz, G. A.; Pollard, R.; Zayats, A. V. Adv. Mater. 2015, 27, 5974.
(b) Wang, L.; Li, X.; Zheng, F.; Guo, Y.; Zhang, Z.; Chi, H.; Dong, Y.; Wang, C.; Lu, G. Acta Chim. Sinica 2016, 74, 259 (in Chinese).(王雷, 李雪, 郑斐, 郭玉鑫, 张志强, 迟海军, 董岩, 王翠苹, 卢公昊, 化学学报, 2016, 74, 259.)
(c) Luo, M.; Ge, J.; Sun, W.; Zhai, H. Acta Chim. Sinica 2016, 74, 839 (in Chinese).(罗曼琳, 葛峻羽, 孙文正, 翟慧芳, 化学学报, 2016, 74, 839.)
[2] Lee, A. S. S.; Lee, J. H.; Lee, J.-C.; Hong, S. M.; Hwang, S. S.; Koo, C. M. J. Mater. Chem. 2014, 2, 1277.
[3] (a) Peng, J.; Xing, Y.; Xu, K.; Lin, W.; Wu, J.; Yu, Z.; Zhang, Y.; Chen, M. J. Mater. Chem. C 2015, 3, 2897.
(b) Peng, J.; Lin, W.; Xing, Y.; Xu, K.; Shuxi, G.; Yuanyuan, R.; Chen, M. Mater. Lett. 2015, 143, 1.
[4] Zhou, Z.; Lu, Z.-R. Nanomedicine 2014, 9, 2387.
[5] Xing, Y.; Peng, J.; Xu, K.; Lin, W.; Gao, S.; Ren, Y.; Gui, X.; Liang, S.; Chen, M. Chem.-Eur. J. 2016, 22, 2114.
[6] (a) Cordes, D. B.; Lickiss, P. D.; Rataboul, F. Chem. Rev. 2010, 110, 2081.
(b) Wen, Y.; Liu, A. Chin. J. Org. Chem. 2005, 25, 470 (in Chinese).(温永向, 刘安华, 有机化学, 2005, 25, 470.)
[7] (a) Kuo, S.-W.; Chang, F.-C. Prog. Polym. Sci. 2011, 36, 1649.
(b) Li, D.; Niu, Y.; Yang, Y.; Wang, X.; Yang, F.; Shen, H.; Wu, D. Chem. Commun. 2015, 51, 8296.
[8] Kraus-Ophir, S.; Jerman, I.; Orel, B.; Mandler, D. Soft Matter 2011, 7, 8862.
[9] Jung, J. H.; Laine, R. M. Macromolecules 2011, 44, 7263.
[10] Tateyama, S.; Kakihana, Y.; Kawakami, Y. J. Organomet. Chem. 2010, 695, 898.
[11] Liu, H.; Puchberger, M.; Schubert, U. Chem.-Eur. J. 2011, 17, 5019.
[12] Lin, H.; Wan, X.; Jiang, X.; Wang, Q.; Yin, J. J. Mater. Chem. 2012, 22, 2616.
[13] Li, Z.; Kawakami, Y. Chem. Lett. 2008, 37, 804.
[14] Wang, L.; Li, J.; Li, L.; Zheng, S. J. Polym. Sci., Part A:Polym Chem. 2013, 51, 2079.
[15] Bassindale, A. R.; Liu, Z.; MacKinnon, I. A.; Taylor, P. G.; Yang, Y.; Light, M. E.; Horton, P. N.; Hursthouse, M. B. Dalton. Trans. 2003, 2945.
[16] (a) Sulaiman, S.; Bhaskar, A.; Zhang, J.; Guda, R.; Goodson Iii, T.; Laine, R. M. Chem. Mater. 2008, 20, 5563.
(b) Wu, L.; Zang, X.; Yan, S.; Tang, S.; Li, Z. Chin. J. Org. Chem. 2014, 34, 596 (in Chinese).(吴林, 臧雄, 阎四海, 唐松青, 李战雄, 有机化学, 2014, 34, 596.)
(c) Zhang, L.; Liu, A.; Zeng, X. Chin. J. Org. Chem. 2007, 27, 424 (in Chinese).(张利利, 刘安华, 曾幸荣, 有机化学, 2007, 27, 424.)
[17] (a) Shchegolikhina, O.; Pozdniakova, Y.; Antipin, M.; Katsoulis, D.; Auner, N.; Herrschaft, B. Organometallics 2000, 19, 1077.
(b) Ito, R.; Kakihana, Y.; Kawakami, Y. Chem. Lett. 2009, 38, 364.
[18] Peng, J.; Xu, K.; Cai, H.; Wu, J.; Lin, W.; Yu, Z.; Chen, M. RSC Adv. 2014, 4, 7124.
[19] Bassindale, A. R.; Parker, D. J.; Pourny, M.; Taylor, P. G.; Horton, P. N.; Hursthouse, M. B. Organometallics 2004, 23, 4400.
[20] Huang, J.-c.; He, C.-b.; Xiao, Y.; Mya, K. Y.; Dai, J.; Siow, Y. P. Polymer 2003, 44, 4491.
[21] Fina, A.; Tabuani, D.; Carniato, F.; Frache, A.; Boccaleri, E.; Camino, G. Thermochim. Acta 2006, 440, 36.
[22] Wang, X.-T.; Yang, Y.-K.; Yang, Z.-F.; Zhou, X.-P.; Liao, Y.-G.; Lv, C.-C.; Chang, F.-C.; Xie, X.-L. J. Therm. Anal. Calorim. 2010, 102, 739.
[23] Xu, K.; Lin, W.; Wu, J.; Peng, J.; Xing, Y.; Gao, S.; Ren, Y.; Chen, M. New J. Chem. 2015, 39, 8405.
[24] (a) Zhang, J.; Xu, R. W.; Yu, D. S. J. Appl. Polym. Sci. 2007, 103, 1004.
(b) Tamaki, R.; Tanaka, Y.; Asuncion, M. Z.; Choi, J.; Laine, R. M. J. Am. Chem. Soc. 2001, 123, 12416.
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