Reviews

Organic Synthesis Based on Cyclodextrins Template Method

  • ZHANG Hua-Cheng ,
  • LIU Zhao-Na ,
  • XIN Fei-Fei ,
  • HAO Ai-You
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  • School of Chemistry & Chemical Engineering, Shandong University, Jinan 250100

Received date: 2011-04-22

  Revised date: 2011-07-01

  Online published: 2011-07-14

Abstract

The organic synthesis based on cyclodextrin template method is reviewed initially by using the “template” concept. These organic synthesis reactions are divided into two main types: one type is based on cyclodextrin “static” template which includes the primary, secondary faces and the cavity. The reactions based on the primary and secondary faces mainly show that the template can control the stereo-structure. While the reactions based on the cavity are mainly using the size and chiral properties of the cavity to do the chemical, regio- and stereo-selectivity, showing that the template can carry out information transfer. The other type is based on cyclodextrin “dynamic” template including the bridge-linked cyclodextrin dimmers with variable conformations and the assemblies prepared by the cyclodextrin derivatives and inclusion complexes. These dynamic templates themselves can be adjusted.

Cite this article

ZHANG Hua-Cheng , LIU Zhao-Na , XIN Fei-Fei , HAO Ai-You . Organic Synthesis Based on Cyclodextrins Template Method[J]. Chinese Journal of Organic Chemistry, 2012 , 32(01) : 30 -45 . DOI: 10.6023/cjoc1104221

References

[1] Szejtli, J. Chem. Rev. 1998, 98, 1743.  

[2] Lecourt, T.; Mallet, J. M.; Sinay, P. Eur. J. Org. Chem. 2003, 4553.

[3] Liu, Y.; You, C.-C.; Zhang, H.-Y. Supramolecular Chemistry: Molecular Recognition and Assembly of Synthetic Receptors, Nankai University Press, Tianjin, 2001 (in Chinese). (刘育, 尤长城, 张衡益, 超分子化学——合成受体的分子识别 与组装, 南开大学出版社, 天津, 2001.)

[4] Weiner, W.; Winkler, J.; Zimmerman, S. C.; Czarnik, A. W.; Breslow, R. J. Am. Chem. Soc. 1985, 107, 4095.

[5] Desper, J. M.; Breslow, R. J. Am. Chem. Soc. 1994, 116, 12081.  

[6] Marinescu, L.; Bols, M. Trends Glycosci. Glycotechnol. 2009, 21, 309.  

[7] Breslow, R. Acc. Chem. Res. 1995, 28, 146.  

[8] Zhao, M.; Hao, A.; Wang, J. Chemistry 2005, 68, w086 (in Chinese). (赵明刚, 郝爱友, 王建英, 化学通报, 2005, 68, w086.)  

[9] Zhao, M.; Hao, A. Chemistry 2006, 69, w001 (in Chinese). (赵明刚, 郝爱友, 化学通报, 2006, 69, w001.)

[10] Canipelle, M.; Landy, D.; Fourmentin, S. J. Inclusion Phenom. Macrocyclic Chem. 2011, 69, 349.  

[11] Kumar, A.; Tripathi, V. D.; Kumar, P. Green Chem. 2011, 13, 51.  

[12] Sun, H.-Y.; Hao, A.-Y.; Yin, M.-J.; Zhang, H.-C.; Shen, J. Prog. Chem. 2008, 20, 1694 (in Chinese). (孙宏元, 郝爱友, 尹明静, 张华承, 申健, 化学进展, 2008, 20, 1694.)

[13] Sun, T.; Sun, T.; Shen, J. Chin. J. Org. Chem. 2009, 29, 681 (in Chinese). (孙涛, 郝爱友, 申健, 有机化学, 2009, 29, 681. )

[14] Jin, T.; Wang, A.; Zhang, J.; Zhao, R.; Liu, B. Chin. J. Org. Chem. 2006, 26, 1723 (in Chinese). (靳通收, 王爱卿, 张建设, 赵瑞巧, 刘利宾, 有机化学, 2006, 26, 1723.)

[15] Rideout, D. C.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 7816.  

[16] Kim, S. P.; Leach, A. G.; Houk, K. N. J. Org. Chem. 2002, 67, 4250.  

[17] Naskar. S.; Saha, P.; Paira, R.; Paira, P.; Hazra, A.; Sahu, K. B.; Banerjee, S.; Mondal, N. B. J. Chem. Res., Synop. 2009, 174.

[18] Ji, H.; Huang, L.; Shi, D.; Zhou, X. Chin. J. Org. Chem. 2008, 28, 2072 (in Chinese). (纪红兵, 黄丽泉, 石东坡, 周贤太, 有机化学, 2008, 28, 2072.)

[19] Breslow, H. Acc. Chem. Res. 1991, 24, 159.  

[20] Xiao, Y.-M.; Fu, B; Li, N.; Tan, Z.-H. Prog. Chem. 2005, 17, 692 (in Chinese). (肖玉梅, 傅滨, 李楠, 覃兆海, 化学进展, 2005, 17, 692. )

[21] Saito, R.; Okuno, Y.; Kobayashi, H. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 3539.  

[22] Saito, R.; Kobayashi, H. Macromolecules 2002, 35, 7207.  

[23] Saito, R. Polymer 2008, 49, 2625.  

[24] Saito, R.; Yamaguchi, K. Macromolecules 2003, 36, 9005.  

[25] Saito, R.; Yamaguchi, K. Macromolecules 2005, 38, 2085.  

[26] Sait o, R.; Kobayashi, H. J. Inclusion Phenom. Macrocycl. Chem. 2002, 44, 303.  

[27] Saito, R.; Yamaguchi, K. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 6262.  

[28] Saito, R.; Yamaguchi, K.; Hara, T.; Saegusa, C. Macromolecules 2007, 40, 4621.  

[29] Rossi, L. I.; Rossi, R. H. Appl. Catal., A 2004, 267, 267.  

[30] Kinen, C. O.; Rossi, L. I.; Rossi, R. H. Appl. Catal. A 2006, 312, 120.  

[31] Ji, H.-B.; Shi, D.-P.; Shao, M.; Li, Z.; Wang, L-F. Tetrahedron Lett. 2005, 46, 2517.  

[32] Tan, K.-Y.; Su, G.-F.; Rao, W.-P.; Tan, G.-M. Chin. J. Org. Chem. 2006, 26, 1623 (in Chinese). (覃开云, 苏桂发, 饶万平, 谭光明, 有机化学, 2006, 26, 1623.)

[33] Surendara, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 9119.  

[34] Krishnaveni, N. S.; Surendra, K.; Nageswar, Y. V. D.; Rao, K. R. Synthesis 2003, 1968.

[35] Anton, L. M.; Dimitri, A. S.; Tatyana, Y.; Filippova, A. Y. Z.; Edward, A. K. Ind. Eng. Chem. Res. 2005, 44, 8644.  

[36] Fenger, T. H.; Bols, M. J. Inclusion Phenom. Macrocyclic Chem. 2011, 69, 397.  

[37] Akkilagunta, V. K.; Reddy, V. P.; Kakulapati, R. R. Synlett 2010, 2517.  

[38] Bjerre, J.; Bols, M. J. Inclusion Phenom. Macrocyclic Chem. 2011, 69, 417.  

[39] Marinescu, L. G.; Doyaguez, E. G.; Petrillo, M.; Fernandez- Mayoralas, A.; Bols, M. Eur. J. Org. Chem. 2010, 157.

[40] Fenger, T. H.; Bjerre, J.; Bols, M. Chem. Biochem. Eng. Q 2009, 23, 2494.

[41] Ji, H.-B.; Huang, L.-Q.; Wu, B. Acta Chim. Sinica 2009, 67, 910 (in Chinese). (纪红兵, 黄丽泉, 吴犇, 化学学报, 2009, 67, 910.)

[42] Fenger, T. H.; Marinescu, L. G.; Bols, M. Org. Biomol. Chem. 2009, 7, 933.  

[43] Machut-Binkowski, C.; Legrand, F. X.; Azaroual, N.; Tilloy, S.; Monflier, E. Chem. Eur. J. 2010, 16, 10195.

[44] Bjerre, J.; Bols, M. Eur. J. Org. Chem. 2010, 3487.

[45] Basilio, N.; Rio, L. G.; Moreira, J. A.; Pessego, M. J. Org. Chem. 2010, 75, 848.  

[46] Sridhar, R.; Srinivas, B.; Madhav, B.; Reddy, V. P.; Nageswar, Y. V. D.; Rao, K. R. Can. J. Chem. 2009, 87, 1704.

[47] Zhang, M.; Gao, Y.; Hu, R. Z.; Shi, Z. Chin. Chem. Lett. 2008, 19, 1139.  

[48] Krishnaveni, N. S.; Surendra, K.; Reddy, M. S.; Negeswar, Y. V. D.; Rao, K. R. Adv. Synth. Catal. 2004, 346, 395.  

[49] Kuppusamy, K.; Pitchumani, K. Tetrahedron Lett. 2010, 51, 3312.  

[50] Murthy, S. N.; Madhav, B.; Reddy, V. P.; Nageswar, Y. V. D. Tetrahedron Lett. 2010, 51, 3649.  

[51] Murthy, S. N.; Madhav, B.; Kumar, A. V.; Rao, K. R.; Nageswar, Y. V. D. Helv. Chim. Acta 2009, 92, 2118.  

[52] Murthy, S. N.; Madhav, B.; Kumar, A. V.; Rao, K. R.; Nageswar, Y. V. D. Tetrahedron, 2009, 65, 5251.  

[53] Kumar, V. P.; Sridhar, R.; Srinivas, B.; Narender, M.; Rao, K. R. Can. J. Chem. 2008, 86, 907.

[54] Bricout, H.; Carbon, L.; Bormann, D.; Monflier, E. Catal. Today 2001, 66, 355.  

[55] Lidia, S.; Liu, J.; Kaifer, A. E. Langmuir 2003, 19, 483.  

[56] Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2005, 127, 5338.  

[57] Torque, C.; Bricoat, H.; Hapiot, F.; Monflier, E. Tetrahedron 2004, 60, 6487.  

[58] Torque, C.; Sueur, B.; Cabou, J.; Bricout, H.; Hapiot, F.; Monflier, E. Tetrahedron 2005, 61, 4811.  

[59] Breslow, R.; Winnik, M. A. J. Am. Chem. Soc. 1969, 91, 3083.  

[60] Palaniswamy, S.; Subramanian, A.; Kasi, P. Tetrahedron 2007, 63, 4959.  

[61] Zhuang, X.-J.; Yuan, F.; Zhang, S.-S. J. Univ. Sci. Technol. 2004, 24, 24 (in Chinese). (庄新杰, 袁枫, 张书圣, 青岛科技大学学报, 2004, 24, 24.)

[62] Shiraishi, Y.; Tomita, H.; Fujiki, K.; Hirai, H. React. Funct. Polym. 1998, 36, 99.  

[63] Shiraishi, Y.; Toshima, N.; Kawamura, T.; Mihori, H.; Shirai, H.; Hirai, H. J. Mol. Catal. A: Chem. 1999, 139, 149.  

[64] Hirai, H. Polym. Adv. Techonl. 1997, 8, 666.  

[65] Mathivet, T.; Méliet, C.; Castanet, Y.; Mortreux, A.; Caron, L.; Tilloy, S.; Monflier, E. J. Mol. Catal. A: Chem. 2001, 176, 105.  

[66] Leclercq, L.; Hapiot, F.; Tilloy, S.; Ramkisoensing, K.; Reek, J. N. H.; Leeuwen, P. W. N. M.; Monflier, E. Organometallics 2005, 24, 2070.  

[67] Leclercq, L.; Sauthier, M.; Castanet, Y.; Mortreux, A.; Bricout, M. H.; Monflier, E. Adv. Synth. Catal. 2005, 347, 55.  

[68] Legrand, F. X.; Sauthier, M.; Flahaut, C.; Hachani, J.; Elfakir, C.; Fourmentin, S.; Tilloy, S.; Monflier, E. J. Mol. Catal. A: Chem. 2009, 303, 72.  

[69] Leclercq, L.; Schmitzer, A. R. Organometallics 2010, 29, 3442.  

[70] Li, W. S.; Chung, W. S.; Chao, I. Chem. Eur J. 2003, 9, 951.

[71] Reddy, M. S.; Srinivas, B.; Sridhar, R.; Narender, M.; Rao, K. R. J. Mol. Catal. A: Chem. 2006, 255, 180.  

[72] Surendra, K.; Krishnaveni, N. S.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 4994.  

[73] Krishnaveni, N. S.; Surendara, K.; Narender, M.; Nageswar, Y. V. D.; Rao, K. R. Synthesis 2004, 501.

[74] Krishnaveni, N. S.; Surendra. K.; Rao, K. R. Adv. Synth. Catal. 2006, 348, 696.  

[75] Somi, R. M.; Narender, M.; Rama, R. K. Tetrahedron Lett. 2005, 46, 1299.  

[76] Banu, H. S.; Pitchumani, K.; Srinivasan, C. Tetrahedron 1999, 55, 9601.  

[77] Koodanjerl, S.; Pradhan, A. R.; Kaanumalle, L. S.; Ramamurthy, V. Tetrahedron Lett. 2003, 44, 3207.  

[78] Komiyama, M.; Hirai, H. J. Am. Chem. Soc. 1983, 105, 2018.  

[79] Ravichandran, R. J. Mol. Catal. A: Chem. 1998, 130, L205.  

[80] Ueno, A. J. Am. Chem. Soc. 1991, 113, 7034.  

[81] Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 966.  

[82] Yang, C.; Nakamura, A.; Fukuhara, G.; Origane, Y.; Mori, T.; Wada, T.; Inoue, Y. J. Org. Chem. 2006, 71, 3126.  

[83] Ikeda, H.; Nihei, T.; Ueno, A. J. Inclusion Phenom. Macrocyclic Chem. 2004, 50, 63.

[84] Ikeda, H.; Nihei, T.; Ueno, A. J. Org. Chem. 2005, 70, 1237.  

[85] Ke, C.; Yang, C.; Mori, T.; Wada, T.; Liu, Y.; Inoue, Y. Angew. Chem., Int. Ed. 2009, 48, 6675.  

[86] Yang, C.; Fukuhara, G.; Nakamura, A.; Origane, Y.; Fujita, K.; Yuan, D. Q.; Mori, T.; Wada, T.; Inoue, Y. J. Photochem. Photobiol., A 2005, 173, 375.  

[87] Yang, C.; Nishijima, M.; Nakamura, A.; Mori, T.; Wada, T.; Inoue, Y. Tetrahedron Lett. 2007, 48, 4357.  

[88] Yang, C.; Nakamura, A.; Wada, T.; Inoue, Y. Org. Lett. 2006, 8, 3005.  

[89] Yang, C.; Mori, T.; Inoue, Y. J. Org. Chem. 2008, 73, 5786.  

[90] Yang, C.; Ke, C.; Kahee, F.; Yuan, D. Q.; Mori, T.; Inoue, Y. Aust. J. Chem. 2008, 61, 565.

[91] Ke, C.; Yang, C.; Liang, W.; Mori, T.; Liu, Y.; Inoue, Y. New J. Chem. 2010, 34, 1323.

[92] Yang, C.; Mori, T.; Origane, Y.; Ko, Y. H.; Selvapalam, N.; Kim, K.; Inoue, Y. J. Am. Chem. Soc. 2008, 130, 8574.  

[93] Fukuhara, G.; Nakamura, T.; Yang, C.; Mori, T.; Inoue, Y. Org. Lett. 2010, 12, 3510.  

[94] Luo, L.; Liao, G. H.; Wu, X. L.; Lei, L.; Tung, C. H.; Wu, L. Z. J. Org. Chem. 2009, 74, 3506.  

[95] Tong, L.-H.; Lu, R.-H.; Inoue, Y. Prog. Chem. 2006, 18, 533 (in Chinese). (童林荟, 鲁润华, 井上佳久, 化学进展, 2006, 18, 533.)

[96] Fukuhara, G.; Mori, T.; Wada, T.; Inoue, Y. J. Org. Chem. 2006, 71, 8233.  

[97] Lu, R.; Yang, C.; Cao, Y.; Wang, Z.; Wada, T.; Jiao, W.; Mori, T.; Inoue, Y. Chem. Commun. 2008, 374.

[98] Lu, R.; Yang, C.; Cao, Y.; Tong, L.; Jiao, W.; Wada, T.; Wang, Z.; Mori, T.; Inoue, Y. J. Org. Chem. 2008, 73, 7695.  

[99] Yang, C.; Mori, T.; Wada, T.; Inoue, Y. New J. Chem. 2007, 31, 697.

[100] Koodanjeri, S.; Joy, A.; Ramamurthy, V. Tetrahedron 2000, 56, 7003.  

[101] Rao, K. S. S. P.; Hubig, S. M.; Moorthy, J. N.; Kochi, J. K. J. Org. Chem. 1999, 64, 8098.  

[102] Shailaja, J.; Karthikeyan, S.; Ramamurthy, V. Tetrahedron Lett. 2002, 43, 9335.  

[103] Cyril, R.; Brian, C.; Mikael, B. Eur. J. Org. Chem. 2005, 13, 2734.

[104] Gandofli, R.; Borrometi, A.; Romano, A.; Gago, J. V. S.; Molinari, F. Tetrahedron: Asymmetry 2002, 13, 2345.  

[105] Mojr, V.; Herzig, V.; Budesinsky, M.; Cibulka, R.; Kraus, T. Chem. Commun. 2010, 46, 7599.  

[106] Artur, R. A.; Iva, C.; Carla, R.; Lu?sa, M. F.; Ana, L.; Pedro, P. S. Tetrahedron 2005, 61, 11986.  

[107] Armspach, D.; Matt, D.; Toupet, L. Angew. Chem., Int. Ed. 2009, 48, 4555.  

[108] Chan, W. S.; Yu, W. Y.; Che, C. M.; Wong, M. K. J. Org. Chem. 2003, 68, 6576.  

[109] Deng, F.; Lan, Zh.-L.; Yin, D.-L.; Xiao, Z.-S. Chemistry 2006, 69, 362 (in Chinese). (邓芳, 兰支利, 尹笃林, 肖自胜, 化学通报, 2006, 69, 362.)

[110] Li, C.-H.; Lan, Z.-L.; Yin, D.-L.; Yu, H.-J. Ind. Catal. 2008, 16, 37 (in Chinese). (李传华, 兰支利, 尹笃林, 于红杰, 工业催化, 2008, 16, 37.)

[111] Schlatter, A.; Kunda, M. K.; Woggon, W. D. Angew. Chem. Int. Ed. 2004, 43, 6731.  

[112] Yang, C. L.; Cheung, Y. K.; Yao, J. Z.; Wong, T. Y.; Jia, G. Organometallics 2001, 20, 424.  

[113] Yang, C. L.; Wong, Y. T.; Li, Z. Y.; Krepinsky, J. J.; Jia, G. Organometallics 2001, 20, 5220.  

[114] Wong, Y. T.; Yang, C. L.; Ying, K. C.; Jia, G. Organometallics 2002, 21, 1782.  

[115] Shen, Z.-X.; Ding, Y.; Liu, Y.-H.; Zhang, Y.-W. Chin. J. Org. Chem. 2005, 25, 1113 (in Chinese). (沈宗旋, 丁一, 李明, 刘艳华, 张雅文, 有机化学, 2005, 25, 1113 )  

[116] Shen, Z.-X.; Ma, J.-M.; Liu, Y.-H.; Jiao, C.-J.; Li, M.; Zhang, Y.-W. Chirality. 2005, 17, 556.  

[117] Kanagaraj, K.; Suresh, P.; Pitchumani, K. Org. Lett. 2010, 12, 4070.  

[118] Suresh, P.; Pitchumani, K. Tetrahedron: Asymmetry 2008, 19, 2037.  

[119] Guieu, S.; Zaborova, E.; Bleriot, Y.; Poli, G.; Jutand, A.; Madec, D.; Prestat, G.; Sollogoub, M. Angew. Chem., Int. Ed. 2010, 49, 2314.

[120] Liu, Y.; Chem, Y. Acc. Chem. Res. 2006, 39, 681.  

[121] Zhang, H.-C.; Hao, A.-Y.; Shen, J. Chin. J. Org. Chem. 2008, 28, 954 (in Chinese). (张华承, 郝爱友, 申健, 有机化学, 2008, 28, 954.)

[122] Zhang, H.-C.; Liu, Z.-N.; An, W.; Hao, A.-Y.; Sun, L.-Z. Chin. J. Org. Chem. 2010, 30, 1279 (in Chinese). (张华承, 刘召娜, 安伟, 郝爱友, 孙立臻, 有机化学, 2010, 30, 1279.)

[123] Easton, C. J.; Lincoln, S. F.; Barr, L.; Onagi, H. Chem. Eur. J. 2004, 10, 3120.  

[124] Blenke, C.; Silva, V. J. D.; Junqueira, M. A. G.; Almeida, W. B. D.; Santos, H. F. D. J. Mol. Struct. THEOCHEM 2007, 809, 95.  

[125] Easton, C. J.; Harper, J. B.; Lincoln, S. F. New J. Chem. 1998, 1163.  

[126] Harper, J. B.; Easton, C. J.; Lincoln, S. F. Tetrahedron Lett. 2003, 44, 5815.  

[127] Bommel, K. J. C.; Jong, M. R.; Metselaar, G. A.; Verboom, W.; Huskens, J.; Hulst, R.; Kooijman, H.; Spek, A. L.; Reinhould, D. N. Chem. Eur. J. 2001, 7, 3603.

[128] Zhou, Y. H.; Zhao, M.; Mao, Z. W.; Ji, L. N. Chem. Eur. J. 2008, 14, 7193.

[129] Tang, S. P.; Chen, S.; Wu, G. F.; Chen, H. Y.; Mao, Z. W.; Ji, L. N. Inorg. Chem. Commun. 2011, 14, 184.  

[130] Ikeda, H.; Nishikawa, S.; Yamamoto, Y.; Ueno, A. J. Mol. Catal. A: Chem. 2010, 328, 1.  

[131] Six, N.; Menuel, S.; Bricout, H.; Hapiot, F.; Monflier, E. Adv. Synth. Catal. 2010, 352, 1467.  

[132] Zhang, H.-C.; Hao, A.-Y.; Li, G.-Z.; Sun, H.-Y. Chin. J. Org. Chem. 2009, 29, 166 (in Chinese). (张华承, 郝爱友, 李干左, 孙宏元, 有机化学, 2009, 29, 166.)

[133] Zhang, H.; Xin, F.; Li, Y.; Hao, A.; An, W.; Sun, T. Prog. Chem. 2010, 22, 2276 (in Chinese). (张华承, 辛飞飞, 李月明, 郝爱友, 安伟, 孙涛, 化学进展, 2010, 22, 2276.)

[134] Leclercq, L.; Lacour, M.; Sanon, S. H.; Schmitzer, A. R. Chem. Eur. J. 2009, 15, 6327.  

[135] Harada, A.; Osaki, M.; Takashima, Y.; Yamaguchi, H. Acc. Chem. Res. 2008, 41, 1143.  

[136] Chen, Q.-R.; Liu, C.; Liu, F.-Q. Prog. Chem. 2010, 22, 927 (in Chinese). (陈清瑞, 刘畅, 刘凤岐, 化学进展, 2010, 22, 927.)

[137] Prasannan, A.; Truong, T. L. B.; Hong, P. D.; Somanathan, N.; Shown, I.; Imae, T. Langmuir, 2011, 27, 766.  

[138] Zhang, H.; Sun, L.; Liu, Z.; An, W.; Hao, A.; Xin, F.; Shen, J. Colloid Surf., A 2010, 358, 115.  

[139] Hu, X.; Lu, Y.; Liu, J. Macromol. Rapid Commun. 2004, 25, 1117.  

[140] Feng, J.; Yan, W.; Zhu, J. Synth. Met. 2010, 160, 939.  

[141] Badi, N.; Guegan, P.; Legrand, F. X.; Leclercq, L.; Tilloy, S.; Monflier, E. J. Mol. Catal. A: Chem. 2010, 318, 8.  

[142] Fang, L; Olson, M. A.; Benitez, D.; Tkatchouk, E.; Goddard, W. A.; Stoddart, J. F. Chem. Soc. Rev. 2010, 39, 17.  

[143] Smaldone, R. A.; Forgan, R. S.; Furukawa, H.; Gassensmith, J. J.; Slawin, A. M. Z.; Yaghi, O. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2010, 49, 8630.  

[144] Kang, Y.; Zhou, L.; Li, X.; Yuan, J. J. Mater. Chem. 2011, 21, 3704.  

[145] Hamasaka, G.; Muto, T.; Uozumi, Y. Angew. Chem., Int. Ed. 2011, 50, 4876.  

[146] Stoll, R. S.; Hecht, S. Angew. Chem., Int. Ed. 2010, 49, 5054.  
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