柱芳烃化学：从合成、主客体性质到自组装性能的研究进展
收稿日期: 2014-08-11
修回日期: 2014-09-22
网络出版日期: 2014-09-22
基金资助
项目受国家自然科学基金(No. 21202145)和中国博士后基金(No. 2013M541767)资助.
Pillar[n]arenes： From Synthesis, Host-Guest Chemistry to Self-Assembly Properties and Applications
Received date: 2014-08-11
Revised date: 2014-09-22
Online published: 2014-09-22
Supported by
Project supported by the National Natural Science Foundation of China (No. 21202145) and the China Postdoctoral Science Foundation (No. 2013M541767).
岳诗雨 , 周玉娟 , 姚勇 , 薛敏 . 柱芳烃化学：从合成、主客体性质到自组装性能的研究进展[J]. 化学学报, 2014 , 72(10) : 1053 -1069 . DOI: 10.6023/A14080579
The study of chemistry based on macrocyclic host is always an important aspect in supramolecular chemistry. As a new class of supramolecular macrocyclic hosts after crown ethers, cyclodextrins, calixarenes, and cucurbiturils, pillar[n]arenes, are useful and interesting macrocyclic compounds that present a hydrophobic core sandwiched between two functionalizable rims. Their syntheses, conformational mobility, derivatization, host-guest complexation, self-assembly in water or organic solvents and applications have been widely explored recently. They have been described as “a new class of macrocycles for supramolecular chemistry”. In this review, we provide a comprehensive overview of pillararene chemistry, summarizing our results along with related studies from other researchers. We describe strategies for the synthesis, isomerization, and functionalization of pillararenes. We also discuss their host-guest properties, their self-assembly into micelles, vesicles, microtubes, supramolecular polymers, and other nanomaterials. The hydroxyl groups of the pillararenes can be modified at all positions or selectively on one or two positions. Through a variety of functionalizations, researchers have developed many pillararene derivatives that exhibit very interesting host-guest properties both in organic solvents and in aqueous media. Guest molecules include electron acceptors such as viologen derivatives and (bis)imidazolium cations and alkyl chain derivatives such as n-hexane, alkanediamines, n-octyltrimethyl ammonium, and neutral bis(imidazole) derivatives. These host-guest studies have led to the fabrication of (pseudo)rotaxanes, poly(pseudo)rotaxanes, supramolecular dimers or polymers. At last, pillararenes applied in molecular recognition, artificial transmembrane proton channels, fluorescent sensors, TNT adsorption, catalysis, biological detoxification, nanoparticles and other areas.
[1] (a) Lehn, J. M. Science 1985, 227, 849.
(b) Sun, Y.; Yan, C.-G.; Yao, Y.; Han, Y.; Shen, M. Adv. Funct. Mater. 2008, 18, 3981.
(c) Guan, B.; Jiang, M.; Yang, X.; Liang, Q.; Chen, Y. Soft Matter 2008, 4, 1393.
(d) Sun, Y.; Yao, Y.; Yan, C.-G.; Han, Y.; Shen, M. ACS Nano 2010, 4, 2129.
(e) Han, C.; Zhang, Z.; Chi, X.; Zhang, M.; Yu, G.; Huang, F. Acta Chim. Sinica 2012, 70, 1775. (韩成友, 张子彬, 池小东, 张明明, 喻国灿, 黄飞鹤, 化学学报, 2012, 70, 1775.)
(f) Yi, J.; Xiao, X.; Zhang, Y.; Xue, S.; Tao, Z.; Zhang, J. Acta Chim. Sinica 2014, 72, 949. (易君明, 肖欣, 张云黔, 薛赛凤, 陶朱, 张建新, 化学学报, 2014, 72, 949.)
(g) Xue, M.; Hu, S.; Chen, C. Acta Chim. Sinica 2012, 70, 1697. (薛敏, 胡树振, 陈传峰, 化学学报, 2012, 70, 1697.)
(h) Yao, Y.; Sun, Y.; Han, Y.; Yan, C. Chin. J. Chem. 2010, 28, 705.
[2] (a) Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T. A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022.
(b) Li, C.; Zhao, L.; Li, J.; Ding, X.; Chen, S.; Zhang, Q.; Yu, Y.; Jia, X. Chem. Commun. 2010, 46, 9016.
(c) Ma, Y.; Chi, X.; Yan, X.; Liu, J.; Yao, Y.; Chen, W.; Hou, J.-L.; Huang, F. Org. Lett. 2012, 14, 1532.
(d) Zhang, Z.; Han, C.; Yu, G.; Huang, F. Chem. Sci. 2012, 3, 3026.
(e) Wei, P.; Yan, X.; Li, J.; Ma, Y.; Yao, Y.; Huang, F. Tetrahedron 2012, 68, 9179.
(f) Wei, P.; Yan, X.; Li, J.; Ma, Y.; Huang, F. Chem. Commun. 2013, 49, 1070.
(g) Dong, S.; Zheng, B.; Yao, Y.; Han, C.; Yuan, J.; Antonietti, M.; Huang, F. Adv. Mater. 2013, 25, 6864.
(h) Fan, J.; Deng, H.; Li, J.; Jia, X.; Li, C. Chem. Commun. 2013, 49, 6343.
(i) Chen, W.; Zhang, Y.; Li, J.; Lou, X.; Yu, Y.; Jia, X.; Li, C. Chem. Commun. 2013, 49, 7956.
(j) Song, N.; Chen, D.-X.; Qiu, Y.-C.; Yang, X.-Y.; Xu, B.; Tian, W.; Yang, Y.-W. Chem. Commun. 2014, 50, 8231.
(k) Wang, Y.; Xu, J.-F.; Chen, Y.-Z.; Niu, L.-Y.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. Chem. Commun. 2014, 50, 7001.
(l) Li, Z.-Y.; Zhang, Y.; Zhang, C.-W.; Chen, L.-J.; Wang, C.; Tan, H.; Yu, Y.; Li, X.; Yan, H.-B. J. Am. Chem. Soc. 2014, 136, 8577.
(m) Zhou, Y.; Li, Z.; Chi, X.; Thompson, C.; Yao, Y. Chem. Commun. 2014, 50, 10482.
(n) Wen, K.; Hu, W.-B.; Yang, H.-M.; Hu, W.-J.; Ma, M.-L.; Zhao, X.-L.; Mi, X.-Q.; Liu, Y.; Li, J.-S.; Jiang, B. Chem. Commun. 2014, 50, 10460.
(o) Li, C. Chem. Commun. 2014, 50, 12420.
(p) Yao, Y.; Wang, Y.; Huang, F. Chem. Sci. 2014, DOI: 10.1039/C4SC01647E.
(q) Wu, X.; Duan, Q.-P.; Ni, M.-F.; Hu, X.-Y.; Wang, L.-Y. Chin. J. Org. Chem. 2014, 34, 437. (吴旋, 段群鹏, 倪梦飞, 胡晓玉, 王乐勇, 有机化学, 2014, 34, 437.)
(r) Zhang, H.-C.; Liu, Z.-N.; Xin, F.-F.; Hao, A.-Y. Chin. J. Org. Chem. 2012, 32, 219. (张华承, 刘召娜, 辛飞飞, 郝爱友, 有机化学, 2012, 32, 219.)
(s) Pan, M.; Xue, M. Chin. J. Chem. 2014, 32, 128.
[3] Ogoshi, T.; Aoki, T.; Kitajima, K.; Fujinami, S.; Yamagishi, T. A.; Nakamoto, Y. J. Org. Chem. 2011, 76, 328.
[4] Cao, D.; Kou, Y.; Liang, J.; Chen, Z.; Wang, L.; Meier, H. Angew. Chem. Int. Ed. 2009, 48, 9721.
[5] Ma, Y.; Zhang, Z.; Ji, X.; Han, C.; He, J.; Abliz, Z.; Chen, W.; Huang, F. Eur. J. Org. Chem. 2011, 5331.
[6] Holler, M.; Allenbach, N.; Sonet, J.; Nierengarten, J. F. Chem. Commun. 2012, 48, 2576.
[7] Wang, K.; Tan, L. L.; Chen, D. X.; Song, N.; Xi, G.; Zhang, S. X.; Li, C.; Yang, Y.-W. Org. Biomol. Chem. 2012, 10, 9405.
[8] Sonawane, M. P.; Jacobs, J.; Thomas, J.; Van Meervelt, L.; Dehaen, W. Chem. Commun. 2013, 49, 6310.
[9] Hu, X.-B.; Chen, Z.; Chen, L.; Zhang, L.; Hou, J.-L.; Li, Z.-T. Chem. Commun. 2012, 48, 10999.
[10] Ogoshi, T.; Ueshima, N.; Sakakibara, F.; Yamagishi, T.-A.; Haino, T. Org. Lett. 2014, 16, 2896.
[11] Ogoshi, T.; Shiga, R.; Yamagishi, T. A.; Nakamoto, Y. J. Org. Chem. 2011, 76, 618.
[12] Ogoshi, T.; Masaki, K.; Shiga, R.; Kitajima, K.; Yamagishi, T. A. Org. Lett. 2011, 13, 1264.
[13] Ogoshi, T.; Hashizume, M.; Yamagishi, T. A.; Nakamoto, Y. Chem. Commun. 2010, 46, 3708.
[14] Ogoshi, T.; Shiga, R.; Hashizume, M.; Yamagishi, T. A. Chem. Commun. 2011, 47, 6927.
[15] Hu, X. B.; Chen, L.; Si, W.; Yu, Y.; Hou, J. L. Chem. Commun. 2011, 47, 4694.
[16] (a) Ma, Y.; Ji, X.; Xiang, F.; Chi, X.; Han, C.; He, J.; Abliz, Z.; Chen, W.; Huang, F. Chem. Commun. 2011, 47, 12340.
(b) Yao, Y.; Li, J.; Dai, J.; Chi, X.; Xue, M. RSC Adv. 2014, 4, 9039.
[17] (a) Ogoshi, T.; Demachi, K.; Kitajima, K.; Yamagishi, T. A. Chem. Commun. 2011, 47, 7164.
(b) Ogoshi, T.; Yamafuji, D.; Kotera, D.; Aoki, T.; Fujinami, S.; Yamagish, T. J. Org. Chem. 2012, 77, 11146.
[18] Zhang, Z.; Xia, B.; Han, C.; Yu, Y.; Huang, F. Org. Lett. 2010, 12, 3285.
[19] Strutt, N. L.; Forgan, R. S.; Spruell, J. M.; Botros, Y. Y.; Stoddart, J. F. J. Am. Chem. Soc. 2011, 133, 5668.
[20] Pan, M.; Xue, M. RSC Adv. 2014, 4, 260.
[21] Ogoshi, T.; Kitajima, K.; Yamagishi, T. A.; Nakamoto, Y. Org. Lett. 2010, 12, 636.
[22] Yao, Y.; Xue, M.; Chen, J.; Zhang, M.; Huang, F. J. Am. Chem. Soc. 2012, 134, 15712.
[23] Ogoshi, T.; Akutsu, T.; Yamafuji, D.; Aoki, T.; Yamagishi, T. Angew. Chem. Int. Ed. 2013, 52, 8111.
[24] Xue, M.; Yang, Y.; Chi, X.; Zhang, Z.; Huang, F. Acc. Chem. Res. 2012, 45, 1294.
[25] Li, C.; Chen, S.; Li, J.; Han, K.; Xu, M.; Hu, B.; Yu, Y.; Jia, X. Chem. Commun. 2011, 47, 11294.
[26] Liu, L.; Cao, D.; Jin, Y.; Tao, H.; Kou, Y.; Meier, H. Org. Biomol. Chem. 2011, 9, 7007.
[27] Shu, X.; Chen, S.; Li, J.; Chen, Z.; Weng, L.; Jia, X.; Li, C. Chem. Commun. 2012, 48, 2967.
[28] (a) Ma, Y.; Yang, J.; Li, J.; Chi, X.; Xue, M. RSC Adv. 2013, 3, 23953.
(b) Jie, K.; Yao, Y.; Chi, X.; Huang, F. Chem. Commun. 2014, 50, 5503.
[29] Chen, Y.; He, M.; Li, B.; Wang, L.; Meier, H.; Cao, D. RSC Adv. 2013, 3, 21405.
[30] Ogoshi, T.; Yamafuji, D.; Aoki, T.; Yamagishi, T. A. Chem. Commun. 2012, 48, 6842.
[31] Ogoshi, T.; Yamafuji, D.; Aoki, T.; Kitajima, K.; Yamagishi, T. A.; Hayashi, Y.; Kawauchi, S. Chem. Eur. J. 2012, 18, 7493.
[32] Gao, L.; Han, C.; Zheng, B.; Dong, S.; Huang, F. Chem. Commun. 2013, 49, 472.
[33] Hou, X.; Ke, C.; Cheng, C.; Song, N.; Blackburn, A. K.; Sarjeant, A. A.; Botros, Y. Y.; Yang, Y. W.; Stoddart, J. F. Chem. Commun. 2014, 50, 6196.
[34] Yan, X.; Wei, P.; Li, Z.; Zheng, B.; Dong, S.; Huang, F.; Zhou, Q. Chem. Commun. 2013, 49, 2512.
[35] Kitajima, K.; Ogoshi, T.; Yamagishi, T. A. Chem. Commun. 2014, 50, 2925.
[36] Ogoshi, T.; Yamafuji, D.; Aoki, T.; Yamagishi, T. A. J. Org. Chem. 2011, 76, 9497.
[37] Ogoshi, T.; Yoshikoshi, K.; Aoki, T.; Yamagishi, T. A. Chem. Commun. 2013, 49, 8785.
[38] Yu, G.; Han, C.; Zhang, Z.; Chen, J.; Yan, X.; Zheng, B.; Liu, S.; Huang, F. J. Am. Chem. Soc. 2012, 134, 8711.
[39] Chi, X. D.; Xue, M.; Yao, Y.; Huang, F. Org. Lett. 2013, 15, 4722.
[40] Xia, W.; Hu, X. Y.; Chen, Y.; Lin, C.; Wang, L. Chem. Commun. 2013, 49, 5085.
[41] Han, C.; Xia, B.; Chen, J.; Yu, G.; Zhang, Z.; Dong, S.; Hu, B.; Yu, Y.; Xue, M. RSC Adv. 2013, 3, 16089.
[42] Sun, S.; Hu, X.-Y.; Chen, D.; Shi, J.; Dong, Y.; Lin, C.; Pan, Y.; Wang, L. Polym. Chem. 2013, 4, 2224.
[43] Xia, B.; He, J.; Abliz, Z.; Yu, Y.; Huang, F. Tetrahedron Lett. 2011, 52, 4433.
[44] Ogoshi, T.; Demachi, K.; Kitajima, K.; Yamagishi, T. A. Chem. Commun. 2011, 47, 10290.
[45] Li, C. J.; Han, K.; Li, J.; Zhang, H. C.; Ma, J. W.; Shu, X. Y.; Chen, Z. X.; Weng, L. H.; Jia, X. S. Org. Lett. 2012, 14, 42.
[46] Ogoshi, T.; Kayama, H.; Yamafuji, D.; Aoki, T.; Yamagishi, T.-A. Chem. Sci. 2012, 3, 3221.
[47] Shu, X.; Chen, W.; Hou, D.; Meng, Q.; Zheng, R.; Li, C. Chem. Commun. 2014, 50, 4820.
[48] Zhang, Z.; Luo, Y.; Chen, J.; Dong, S.; Yu, Y.; Ma, Z.; Huang, F. Angew. Chem. Int. Ed. 2011, 50, 1397.
[49] Zhang, Z.; Yu, G.; Han, C.; Liu, J.; Ding, X.; Yu, Y.; Huang, F. Org. Lett. 2011, 13, 4818.
[50] Strutt, N. L.; Zhang, H.; Giesener, M. A.; Lei, J.; Stoddart, J. F. Chem. Commun. 2012, 48, 1647.
[51] Wang, K.; Wang, C. Y.; Wang, Y.; Li, H.; Bao, C. Y.; Liu, J. Y.; Zhang, S. X.; Yang, Y.-W. Chem. Commun. 2013, 49, 10528.
[52] Xia, B.; Zheng, B.; Han, C.; Dong, S.; Zhang, M.; Hu, B.; Yu, Y.; Huang, F. Polym. Chem. 2013, 4, 2019.
[53] Ogoshi, T.; Nishida, Y.; Yamagishi, T.-A.; Nakamoto, Y. Macromolecules 2010, 43, 7068.
[54] Ogoshi, T.; Hasegawa, Y.; Aoki, T.; Ishimori, Y.; Inagi, S.; Yamagishi, T. Macromolecules 2011, 44, 7639.
[55] Ji, X.; Chen, J.; Chi, X.; Huang, F. ACS Macro Lett. 2014, 3, 110.
[56] Wang, X.; Han, K.; Li, J.; Jia, X.; Li, C. Polym. Chem. 2013, 4, 3998.
[57] Xu, J. F.; Chen, Y. Z.; Wu, L. Z.; Tung, C. H.; Yang, Q.-Z. Org. Lett. 2013, 15, 6148.
[58] Guan, Y.; Ni, M.; Hu, X.; Xiao, T.; Xiong, S.; Lin, C.; Wang, L. Chem. Commun. 2012, 48, 8529.
[59] Hu, X.-Y.; Zhang, P.; Wu, X.; Xia, W.; Xiao, T.; Jiang, J.; Lin, C.; Wang, L. Polym. Chem. 2012, 3, 3060.
[60] Hu, X. Y.; Wu, X.; Duan, Q.; Xiao, T.; Lin, C.; Wang, L. Org. Lett. 2012, 14, 4826.
[61] Hu, X.-Y.; Wu, X.; Wang, S.; Chen, D.; Xia, W.; Lin, C.; Pan, Y.; Wang, L. Polym. Chem. 2013, 4, 4292.
[62] Zhang, H.; Strutt, N. L.; Stoll, R. S.; Li, H.; Zhu, Z.; Stoddart, J. F. Chem. Commun. 2011, 47, 11420.
[63] Yu, G.; Xue, M.; Zhang, Z.; Li, J.; Han, C.; Huang, F. J. Am. Chem. Soc. 2012, 134, 13248.
[64] Gao, L.; Zheng, B.; Yao, Y.; Huang, F. Soft Matter 2013, 9, 7314.
[65] Yao, Y.; Wei, P.; Yue, S.; Li, J.; Xue, M. RSC Adv. 2014, 4, 6042.
[66] Yao, Y.; Chi, X.; Zhou, Y.; Huang, F. Chem. Sci. 2014, 5, 2778.
[67] Zhang, H.; Ma, X.; Guo, J.; Nguyen, K. T.; Zhang, Q.; Wang, X.-J.; Yan, H.; Zhu, L.; Zhao, Y. RSC Adv. 2013, 3, 368.
[68] Yao, Y.; Xue, M.; Chi, X.; Ma, Y.; He, J.; Abliz, Z.; Huang, F. Chem. Commun. 2012, 48, 6505.
[69] Li, H.; Chen, D. X.; Sun, Y. L.; Zheng, Y. B.; Tan, L. L.; Weiss, P. S.; Yang, Y.-W. J. Am. Chem. Soc. 2013, 135, 1570.
[70] Yao, Y.; Xue, M.; Zhang, Z.; Zhang, M.; Wang, Y.; Huang, F. Chem. Sci. 2013, 4, 3667.
[71] Yao, Y.; Zhou, Y.; Dai, J.; Yue, S.; Xue, M. Chem. Commun. 2014, 50, 869.
[72] Tian, M.; Chen, D.-X.; Sun, Y.-L.; Yang, Y.-W.; Jia, Q. RSC Adv. 2013, 3, 22111.
[73] Chen, D.-X.; Sun, Y.-L.; Zhang, Y.; Cui, J.-Y.; Shen, F.-Z.; Yang, Y.-W. RSC Adv. 2013, 3, 5765.
[74] Wu, L.; Fang, Y.; Jia, Y.; Yang, Y.; Liao, J.; Liu, N.; Yang, X.; Feng, W.; Ming, J.; Yuan, L. Dalton Trans. 2014, 43, 3835.
[75] Fang, Y.; Wu, L.; Liao, J.; Chen, L.; Yang, Y.; Liu, N.; He, L.; Zou, S.; Feng, W.; Yuan, L. RSC Adv. 2013, 3, 12376.
[76] Strutt, N. L.; Fairen-Jimenez, D.; Iehl, J.; Lalonde, M. B.; Snurr, R. Q.; Farha, O. K.; Hupp, J. T.; Stoddart, J. F. J. Am. Chem. Soc. 2012, 134, 17436.
[77] Nierengarten, I.; Guerra, S.; Holler, M.; Nierengarten, J.-F.; Deschenaux, R. Chem. Commun. 2012, 48, 8072.
[78] Si, W.; Chen, L.; Hu, X.-B.; Tang, G.; Chen, Z.; Hou, J.-L.; Li, Z.-T. Angew. Chem. Int. Ed. 2011, 50, 12564.
[79] Hu, X. B.; Chen, Z.; Tang, G.; Hou, J.-L.; Li, Z.-T. J. Am. Chem. Soc. 2012, 134, 8384.
[80] Chen, L.; Si, W.; Zhang, L.; Tang, G.; Li, Z.-T.; Hou, J.-L. J. Am. Chem. Soc. 2013, 135, 2152.
[81] Yu, G.; Zhou, X.; Zhang, Z.; Han, C.; Mao, Z.; Gao, C.; Huang, F. J. Am. Chem. Soc. 2012, 134, 19489.
[82] Duan, Q.; Cao, Y.; Li, Y.; Hu, X.; Xiao, T.; Lin, C.; Pan, Y.; Wang, L. J. Am. Chem. Soc. 2013, 135, 10542.
[83] Wang, P.; Yao, Y.; Xue, M. Chem. Commun. 2014, 50, 5064.
[84] Kothur, R. R.; Hall, J.; Patel, B. A.; Leong, C. L.; Boutelle, M. G.; Cragg, P. J. Chem. Commun. 2014, 50, 852.
[85] Zhang, H.; Ma, X.; Nguyen, K. T.; Zhao, Y. ACS Nano 2013, 7, 7853.
[86] Ogoshi, T.; Shiga, R.; Yamagishi, T. A. J. Am. Chem. Soc. 2012, 134, 4577.
[87] Yu, G.; Ma, Y.; Han, C.; Yao, Y.; Tang, G.; Mao, Z.; Gao, C.; Huang, F. J. Am. Chem. Soc. 2013, 135, 10310.
[88] Ogoshi, T.; Ueshima, N.; Yamagishi, T. Org. Lett. 2013, 15, 3742.
[89] (a) Yang, J.; Chi, X.; Li, Z.; Yu, G.; He, J.; Abliz, Z.; Li, N.; Huang, F. Org. Chem. Front. 2014, 1, 630.
(b) Li, Z.; Yang, J.; Yu, G.; He, J.; Abliz, Z.; Huang, F. Chem. Commun. 2014, 50, 2841.
(c) Li, Z.; Yang, J.; Yu, G.; He, J.; Abliz, Z.; Huang, F. Org. Lett. 2014, 16, 2066.
/
| 〈 |
|
〉 |
