Advance in the Construction and Application of Cyclodextrin- Porphyrin Supramolecular System

doi:10.6023/cjoc1107133

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (04): 686-695.DOI: 10.6023/cjoc1107133 Previous Articles Next Articles

Reviews

环糊精-卟啉超分子体系的构筑及应用进展

陈韶云, 周贤太, 纪红兵

中山大学化学与化学工程学院广州 510275

收稿日期:2011-07-13 修回日期:2011-09-22 发布日期:2012-04-24
通讯作者: 纪红兵 E-mail:jihb@mail.sysu.edu.cn
基金资助:
国家自然科学基金(Nos. 21036009, 20976203, 21176268)、2010 年广东省高等学校高层次人才项目、中央高校基本科研业务费专项资金资助项目.

Advance in the Construction and Application of Cyclodextrin- Porphyrin Supramolecular System

Chen Shaoyun, Zhou Xiantai, Ji Hongbing

School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275

Received:2011-07-13 Revised:2011-09-22 Published:2012-04-24
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21036009, 20976203, 21176268), the Higher-Level Talent Project for Guangdong Provincial Universities (2010) and the Fundamental Research Funds for the Central Universities.

Molecular recognition and selective guest molecular inclusion are the unique performances of cyclodextrin, and porphyrin owns the behavior of biomimetic catalysis, electron transfer and light energy transfer. Based on the introduction of construction ways, the applications of cyclodextrin-porphyrins supramolecular system in biomimetic catalysis, life science, drug delivery and electron transfer were well reviewed. The cyclodextrin-porphyrins supramolecular system endowed with the advantages that concentrated the dual nature of porphyrins and cyclodextrin. The supramolecular system constructed by using the binding cyclodextrin-porphyrins as host molecular could more effectively mimic the behavior of enzymes, showing excellent regional and stereoselectivity. And it will be widely used in biomimetic catalysis.

Key words: cyclodextrin, porphyrin, supramolecular compound, construction

Cite this article

Chen Shaoyun, Zhou Xiantai, Ji Hongbing. Advance in the Construction and Application of Cyclodextrin- Porphyrin Supramolecular System[J]. Chin. J. Org. Chem., 2012, 32(04): 686-695.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Meunier, B. Biomimetic Oxidations Mediated by Metal Complexes, Imperial College Press, London, 2000.

[2] Lovell, J. F.; Liu, T. W. B.; Chen, J.; Zheng, G. Chem. Rev. 2010, 110, 2839.

[3] Haas, K. L.; Franz, K. J. Chem. Rev. 2009, 109, 4921.

[4] Villalonga, R.; Cao, R.; Fragoso, A. Chem. Rev. 2007, 107, 3088.

[5] Chen, H. Y.; Ji, H. B. AIChE. J. 2010, 56, 466.

[6] Zhan, H. Y.; Liu, H. Y.; Hu, J.; Jiang, H. F. Sci. China, Ser. B 2009, 39, 253 (in Chinese). (詹海莺, 刘海洋, 胡军, 江焕峰, 中国科学B辑: 化学, 2009, 39, 253.)

[7] Huang, J.; Ren, L. Y.; Fan, H. L.; Chen, Y. M. Sci. China, Ser. B 2011, 39, 301 (in Chinese). (黄进, 任丽霞, 范红蕾, 陈永明, 中国科学B辑: 化学, 2009, 39, 301.)

[8] Breslow, R.; Zhang, X. J.; Xu, R.; Maletic, M.; Merger, R. J. Am. Chem. Soc. 1996, 118, 11678.

[9] Breslow, R.; Huang, Y.; Zhang, X. J.; Yang, J. Proc. Natl. Acad. Sci. U.S. A. 1997, 94, 11156.

[10] Yu, S. J.; Huang, X.; Miao, L.; Zhu, J. Y.; Yin, Y. Z.; Luo, Q.; Xu, J. Y.; Shen, J. C.; Liu, J. Q. Bioorg. Chem. 2010, 38, 159.

[11] Guo, Y. J.; Zhang, P.; Chao, J. B.; Shuang, S. M.; Dong, C. Spectrochim. Acta A 2008, 71, 946.

[12] Manka, J. S.; Lawrence, D. S. J. Am. Chem. Soc. 1990, 112, 2440.

[13] EL-Hachemi, Z.; Farrera, J. A.; Garcia-Ortega, H.; Ramirez- Gutierrez, O.; Ribo, J. M. J. Porphyrins Phthalocyanines 2001, 5, 465.

[14] Mosinger, J.; Slavetinska, L.; Lang, K.; Coufal, P.; Kubat, P. Org. Biomol. Chem. 2009, 7, 3797.

[15] Hamai, S.; Koshiyama, T. Spectrochim. Acta A 2001, 57, 985.

[16] Kano, K. Colloid Polym. Sci. 2008, 286, 79.

[17] Guo, Y. J.; Guo, L.; Pan, J. H. Phys. Chem. Liq. 2007, 45, 261.

[18] Zhang, H. F.; Pan, J. H.; Gao, Y. L.; Guo, Y. J. Chin. J. Anal. Chem. 2006, 34, 1541 (in Chinese). (张红芬, 潘景浩, 高莜玲, 郭玉晶, 分析化学, 2006, 34, 1541.)

[19] Schneider, H. J. Angew. Chem., Int. Ed. 2009, 48, 3924.

[20] Liu, J.; Xu, D. H.; Mei, W. J.; Pu, H. L.; Huang, J. W.; Ji, L. N.Chem. J. Chin. Univ. 2001, 22, 1446 (in Chinese). (刘杰, 许东晖, 梅文杰, 蒲含林, 黄锦汪, 计亮年, 高等学校化学学报, 2001, 22, 1446.)

[21] Hamai, S. J. Inclusion Phenom. Macrocyclic Chem. 2007, 58, 241.

[22] Qiu, W. G.; Li, Z. F.; Bai, G. M.; Meng, S. N.; Dai, H. X.; He, H. Spectrochim. Acta A 2007, 66, 1189.

[23] Kong, L. H.; Guo, Y. J.; Li, X. X.; Pan, J. H. Chin. J. Anal. Chem. 2007, 35, 537 (in Chinese). (孔令宏, 郭玉晶, 李小香, 潘景浩, 分析化学, 2007, 35, 537.)

[24] Li, X. X.; Wang, J. W.; Guo, Y. J.; Kong, L. H.; Pan, J. H. J. Inclusion Phenom. Macrocyclic Chem. 2007, 58, 307.

[25] Li, X. X.; Guo, Y. J.; Wang, J. W.; Kong, L. H.; Pan, J. H. Supramol. Chem. 2008, 20, 243.

[26] Guo, Y. J.; Zhang, P.; Chao, J. B.; Shuang, S. M.; Dong, C. Spectrochim. Acta A 2008, 71, 946.

[27] Kong, L. H.; Guo, Y. J.; Li, X. X.; Pan, J. H. Spectrochim. Acta A 2007, 66, 594.

[28] Hu, Y.; Zhao, H. B.; Ning, J. H.; Ning, M. X.; Xu, Y. J.; Qiu, S. J.; Liao, J. X. Acta Chim. Sinica 2008, 66, 2391 (in Chinese). (胡羽, 赵鸿斌, 宁静恒, 宁满霞, 徐勇军, 仇诗军, 廖俊旭, 化学学报, 2008, 66, 2391.)

[29] Wang, W. L.; Zhao, H. B.; Ning, J. H.; Hu, Y.; Zhang, H.; Lu, X. J.; Ye, L. Y. Chin. J. Inorg. Chem. 2010, 26, 2025 (in Chinese). (王武林, 赵鸿斌, 宁静恒, 胡羽, 张辉, 陆旭甲, 叶领云, 无机化学学报, 2010, 26, 2025.)

[30] Carofiglio, T.; Fornasler, R.; Lucchini, V.; Simonato, L.; Tonellato, U. J. Org. Chem. 2000, 65, 9013.

[31] Kano, K.; Nishiyabu, R.; Yamazaki, T.; Yamazaki, I. J. Am. Chem. Soc. 2003, 125, 10625.

[32] Sasaki, K.; Nakagawa, H.; Zhang, X. Y.; Sakurai, S.; Kano, K.; Kuroda, Y. Chem. Commun. 2004, 104, 408.

[33] Fathalla, M.; Neuberger, A.; Li, S. C.; Schmehl, R.; Diebold, U.; Jayawickramarajah, J. J. Am. Chem. Soc. 2010, 132, 9966.

[34] Yu, M.; Chen, Y.; Zhang, N.; Liu, Y. Org. Biomol. Chem. 2010, 8, 4148.

[35] Gu, Z. Y.; Guo, D. S.; Sun, M.; Liu, Y. J. Org. Chem. 2010, 75, 3600.

[36] Yu, S. J.; Huang, X.; Miao, L.; Zhu, J. Y.; Yin, Y. Z.; Luo, Q.; Xu, J. Y.; Shen, J. C.; Liu, J. Q. Bioorg. Chem. 2010, 38, 159.

[37] Kiba, T.; Suzuki, H.; Hosokawa, K.; Kobayashi, H.; Baba, S.; Kakuchi, T.; Sato, S. J. Phys. Chem. B 2009, 113, 11560.

[38] Mazzaglia, A.; Valerio, A.; Micali, N.; Villari, V.; Quaglia, F.; Castriciano, M. A.; Scolaro, L. M.; Giuffrè, M.; Siracusano, G.; Sciortino, M. T. Chem. Commun. 2011, 47, 9140.

[39] Ribo, J. M.; Farrera, J. A.; Valero, M. L.; Virgili, A. Tetrahedron 1995, 51, 3705.

[40] Breslow, R.; Gabriele, B.; Yang, J. Tetrahedron Lett. 1998, 39, 2887.

[41] Yang, J.; Gabriele, B; Belvedere, S.; Huang, Y.; Breslow, R. J. Org. Chem. 2002, 67, 5057.

[42] Kuroda, Y.; Hiroshige, T.; Sera, T.; Shiroiwa, Y.; Tanaka, H.; Ogoshi, H. J. Am. Chem. Soc. 1989, 111, 1912.

[43] Kuroda, Y.; Hiroshige, T.; Sera, T.; Ogoshi, H. Carbohydr. Res. 1989, 192, 347.

[44] Kuroda, Y.; Sera, T.; Ogoshi, H. J. Am. Chem. Soc. 1991, 113, 2793.

[45] Weber, L.; Imiolczyk, I.; Haufe, G.; Rehorek, D.; Hennig, H. J. Chem. Soc., Chem. Commun. 1992, 301.

[46] French, R. R.; Holzer, P.; Leuenberger, M.; Nold, M. C.; Woggon, W. D. J. Inorg. Biochem. 2002, 88, 295.

[47] French, R. R.; Wirz, J.; Woggon, W. D. Helv. Chim. Acta 1998, 81, 1521.

[48] French, R. R.; Holzer, P.; Leuenberger, M. G.; Woggon W. D. Angew. Chem., Int. Ed. 2000, 39, 1267.

[49] Lee, J. B.; Hunt, J. A.; Grove, J. T. J. Am. Chem. Soc. 1998, 120, 7493.

[50] Li, Z. Y.; Li, J. F.; Li, C. Chin. J. Chem. 2002, 20, 399.

[51] Li, Z. Y.; Li, C.; Wu, X. Y.; Zhang, Y. N. Chin. Chem. Lett. 2000, 11, 493.

[52] Kralova, J.; Kejik, Z.; Briza, T.; Pouckova, P.; Kral, A.; Martasek, P.; Kral, V. J. Med. Chem. 2010, 53, 128.

[53] Chen, W. H.; Yan, J. M.; Tagashira, Y.; Yamaguchi, M.; Fujita, K. Tetrahedron Lett. 1999, 40, 891.

环糊精-卟啉超分子体系的构筑及应用进展

Advance in the Construction and Application of Cyclodextrin- Porphyrin Supramolecular System

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jing Sun, Mengmeng Zhang, Xiaolong Guo, Qi Wang, Luyao Wang. Synthesis of Diaryl Selenium Compounds without Transition-Metal Catalyst [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4251-4260.
[2]	Jiajia Lu, Junli Yang, Jie Gu, Ju Yang, Zhenjie Gao, Lijiao Su, Xin Tao, Mingwei Yuan, Lijuan Yang. Mono-(6-diethylenetriamine-6-deoxy)-β-cyclodextrin Supramolecular Fluorescent Switch Constructed Based on Au³⁺ and I^– [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1474-1482.
[3]	Liwei Xiao, Guangxian Liu, Ping Ren, Tongtong Wu, Yuwei Lu, Jie Kong. Elemental Sulfur: An Excellent Sulfur-Source for Synthesis of Sulfur-Containing Heterocyclics [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1002-1012.
[4]	Yuqing He, Lin Chen, Ruili He, Keli Zhong, Lijun Tang. Research Progress of Fluorescence Probes Constructed by Cyclodextrin Derivatives and Inclusion Complexes [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 785-795.
[5]	Qihang Zhao, Longchang Tang, Peng Jiao. Construction of Spiro Skeletons in 2,2',3,3'-Tetrahydro-1,1'- spirobi[1H-indene]-7,7'-diol (SPINOL) and Analogues [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3400-3413.
[6]	Junfeng Qian, Xiaoting Tian, Zhong Wu, Jie Yao, Hui Wang, Weiyou Zhou. Efficient Oxidative Coupling of Isochroman with Primary Arylamines Catalyzed by Heterogeneous Ni-Containing Layered Double Oxide [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3668-3674.
[7]	Jingjing Guo, Minjie Guo. Progress in Design and Application of Supramolecular Fluorescent Systems Based on Difluoroboron-Dipyrromethene and Macrocyclic Compounds [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2946-2963.
[8]	Xing Chen, Xuan Zhou, Xiaochen Ji, Huawen Huang. Visible Light-Induced Aerobic Oxidative Dehydrogenative Coupling of Thiophenols [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4704-4711.
[9]	Shuhua He, Hang Zhang, Hongyu Wu, Shiyu Zhou, Yao Xiao, Xianhui You, Jinyang Chen. ICl-Catalyzed C_sp2—H Selenation of Aminocoumarin Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4378-4383.
[10]	Sun Kai, Liu Haidong, Xie Qi, Luo Haiqing. Progress in the Synthesis of Arylphosphonates via Ar-P Bond Construction [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2275-2289.
[11]	Ouyang Banlai, Zheng Yanxia, Xia Kejian, Xu Xiaoling, Wang Yi. Recent Progress in Transition Metal Catalyzed Sulfonamidation of Aromatic Compounds [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1188-1205.
[12]	Zhang Yi, Liu Yu. Supramolecular Assemblies of Multi-Charged Cyclodextrins [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3802-3811.
[13]	Zhou Xiang, Zhou Fei, Jia Xiaoliang, Yu Jiawei, Shen Qi, Zhang Yunxiao, Shi Weimin. Solvent-Free Aldol Reaction of β-Porphyrin Formaldehyde with Ketone [J]. Chin. J. Org. Chem., 2019, 39(7): 2084-2088.
[14]	Chen Yaqi, Gui Xin, Duan Zunbin, Zhu Lijun, Xiang Yuzhi, Xia Daohong. Transition Metal Catalyzed Organic Reaction Involving Cyclodextrin [J]. Chin. J. Org. Chem., 2019, 39(5): 1284-1292.
[15]	Peng Suhong, Zhou Rong, Zou Huaibo. Research Progress in N-Confused Porphyrins [J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3384-3398.