中文
Announcement
More
Progress in Chemistry 2008, Vol. 20 Issue (05): 713-719 Previous Articles   Next Articles

• Review •

Modification of Porphyrin by 1,3-Dipolar Cycloaddition

Wang Lei; Feng Yaqing**; Zhao Bing; Xue Jinqiang; Li Yukun   

  1. (School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China)
  • Received: Revised: Online: Published:
  • Contact: Feng Yaqing
PDF ( 1440 ) Cited
Export

EndNote

Ris

BibTeX

Recently, the modification of porphyrin by 1,3-dipolar cycloaddition has been studied intensively. The cycloaddition product plays an important role in photodynamic therapy (PDT) as potential photosensitizer or in artificial photoreaction center due to its characteristic long-wavelength absorption bands. The progress on modification of porphyrin by 1,3-dipolar cycloaddition is reviewed. The synthesis of novel heterocyclic-fused chlorins and bacteriochlorins by the reactions of the peripheral double bonds of the porphyrin macrocycle with the 1, 3-dipoles such as azomethine ylide, nitrones, diazomethane, carbonyl ylide, nitrile oxide is discussed. The synthesis of new β-substituted porphyrin derivatives by the reactions of porphyrin dipoles with dipolarophiles such as C60 etc. is discussed and the 1,3-dipolar cycloaddition of expanded porphyrin with azomethine ylide is referred.

CLC Number: 

[ 1 ] Kadish K M, Smith K M, Guilard R , et al . The Porphyrin Handbook , NY: Academic Press , 2000. vol . 1 , 151
[ 2 ] Li X F , Li YL , Zhu D B , et al . J . Org. Chem. , 2006 , 71 :9739 —9742
[ 3 ] Li X F , Li YL , Zhu D B , et al . Org. Lett . , 2006 , 8 : 1137 —1140
[ 4 ] Wasielewski M R. Chem. Rev. , 1992 , 92 : 435 —461
[ 5 ] Terazono Y, Kodis G, Andreasson J , et al . J . Phys. Chem. B ,2004 , 108 : 1812 —1814
[ 6 ] Guldi D M. J . Phys. Chem. B , 2005 , 109 : 11432 —11441
[ 7 ] Chen C T. Chem. Mater. , 2004 , 16 : 4389 —4400
[ 8 ] 孙景志(Sun J Z) , 汪茫(Wang M) , 周成(Zhou C) 等. 功能材料(Journal of Functional Materials) , 2003 , 34(1) : 100 —102
[ 9 ] 朱宝库(Zhu B K) , 徐又一(Xu Y Y) , 徐志康(Xu Z K) . 功能高分子学报(Journal of Functional Polymers) , 2003 , 16 (2) :141 —148
[10] Zhang X H , Xie Z Y, Wu F P , et al . Chem. Phys. Lett . , 2003 ,382 : 561 —566
[11] Takahashi K, Kuraya N , Yamaquchi T , et a1. Solar Energy Materials &Solar Cell , 2000 , 61 : 403 —416
[12] Lidzey D G, Bradley D D C , Skolnick MS , et al . Nature , 1998 ,395 : 53 —55
[13] Banfi S , Caruso E , Buccafurni L , et al . J . Photochemistry & Photobiology B : Biology , 2006 , 85 : 28 —38
[14] Xiao S Q , Mohamed E , Li Y L , et al . J . Phys. Chem. B , 2005 ,109 : 3658 —3667
[15] Li Y J , Gan Z H , Li Y L , et al . Tetrahedron , 2006 , 62 : 4285 —4293
[16] Sternberg E D , Dolphin D , Brückner C. Tetrahedron , 1998 , 54 :4151 —4202
[17] Cavaleiro J A S , Neves M G P M S , ToméA C. Arkivoc , 2003 ,(14) : 107 —130
[18] Silva A M G, ToméA C , Neves M G P M S , et al . Tetrahedron Lett . , 2005 , 46 : 4723 —4726
[19] 方勇(Fang Y) , 徐德余(Xu D Y) , 刘建飞(Liu J F) . 中国激光医学杂志( Chinese Journal of Laser Medicine & Surgery) .2001 , 10(2) : 82 —85
[20] Silva A M G, ToméA C , Neves M G P M S , et al . Chem.Commun. , 1999 , (17) : 1767 —1768
[21] ToméA C , Lacerda P S S , Silva A M G, et al . J . Porphyrins Phthalocyanines , 2000 , 4 : 532 —537
[22] Maestrin A P J , Ribeiro A O , Tedesco A C , et al . J . Braz.Chem. Soc. , 2004 , 15 : 923 —930
[23] Silva A M G, Tomé A C , Neves M G P M S , et al . J . Org.Chem. , 2005 , 70 : 2306 —2314
[24] Silva A M G, Tomé A C , Cavaleiro J A S , et al . Synlett , 2005 ,5 : 857 —859
[25] Ga¤ ìzowski M, Gryko T D. J . Org. Chem. , 2006 , 71 : 5942 —5950
[26] Silva A M G, Cavaleiro J A S , Perrone D , et al . Tetrahedron Lett . , 2002 , 43 : 603 —605
[27] Black D S C , Crozier R F , Davis V C , et al . Synthesis , 1975 ,4 : 205 —221
[28] Silva A M G, ToméA C , Neves M G P M S , et al . Synlett ,2002 , 7 : 1155 —1157
[29] Desjardins A , Flemming J , Sternberg E D , et al . Chem.Commun. , 2002 , 2622 —2623
[30] Werner A , Buss H. Chem. Ber. , 1894 , 27 : 2193 —2201
[31] Flemming J , Dolphin D. Tetrahedron Lett . , 2002 , 43 : 7281 —7283
[32] Liu X G, Feng Y Q , Chen X, et al . Synlett , 2005 , 6 : 1030 —1032
[33] Liu X G, Feng Y Q , Hu X F , et al . Synthesis , 2005 , 20 :3632 —3638
[34] Ostrowski S , Wyrebek P , Mikus A. Heterocycles , 2006 , 68 :885 —888
[35] Drovestskaya T , Reed C A. Tetrahedron Lett . , 1995 , 36 :7971 —7974
[36] Helaja J , Tauber A Y, Abel Y, et al . J . Chem. Soc. Perkin Trans. , 1999 , 2403 —2408
[37] Efimov A , Tkatchenko N V , Vainiotalo P , et al . J . Porphyrins Phthalocyaines , 2001 , 5 : 835 —838
[38] Silva A M G, ToméA C , Neves M G P M S , et al . J . Org.Chem. , 2002 , 67 : 726 —732
[39] Liu X G, Feng Y Q , Tan C J . Syn. Commun. , 2006 , 36 :2655 —2659
[40] Silva A M G, Lacerda P S S , ToméA C , et al . J . Org. Chem. ,2006 , 71 : 8352 —8356
[41] Morozova Y V , Starikova Z A , Maksimov B I. Russ. Chem.Bull . Int . Ed. , 2004 , 53 : 2192 —2206
[42] Furuta H , Maeda H , Osuka A. Chem. Commun. , 2002 , 1795 —1804
[43] Jasat A , Dolphin D. Chem. Rev. , 1997 , 97 : 2267 —2340
[44] Tanaka Y, Hoshino W, Shimizu S , et al . J . Am. Chem. Soc. ,2004 , 126 : 3046 —3047
[45] Suzuki M, Shimizu S , Osuka A , et al . Tetrahedron Lett . , 2003 ,44 : 4597 —4601
[46] Hata H , Shinokubo H , Osuka A. Angew. Chem. Int . Ed. ,2005 , 44 : 932 —935
[47] Hata H , Kamimura Y, Shinokubo H , et al . Org. Lett . , 2006 ,8 : 1169 —1172

[1] Chenliu Tang, Yunjie Zou, Mingkai Xu, Lan Ling. Photocatalytic Reduction of Carbon Dioxide with Iron Complexes [J]. Progress in Chemistry, 2022, 34(1): 142-154.
[2] Haichao Wang, Mingjin Tang, Zhaofeng Tan, Chao Peng, Keding Lu. Atmospheric Chemistry of Nitryl Chloride [J]. Progress in Chemistry, 2020, 32(10): 1535-1546.
[3] Yawei Wang, Ying Wang, Guibin Jiang. Analytical Methods, Environmental Pollutions and Toxicity of Short Chain Chlorinated Paraffins [J]. Progress in Chemistry, 2017, 29(9): 919-929.
[4] Zhu Zhang, Qiyong Jiang, Jiazhu Li, Jinjun Wang. Rearrangement Reactions of Chlorophyllous Tetrapyrrole Macrocyclic Molecules [J]. Progress in Chemistry, 2017, 29(2/3): 262-284.
[5] Chen Maolong, Yin Bangshao, Song Jianxin. Recent Development of Constructing Porphyrin Arrays via Suzuki-Miyaura Cross-Coupling Reaction [J]. Progress in Chemistry, 2015, 27(6): 641-654.
[6] Niu Fanfan, Nie Changjun, Chen Yong, Sun Xiaoling. Asymmetric Catalytic Epoxidation of Unfunctionalized Olefins [J]. Progress in Chemistry, 2014, 26(12): 1942-1961.
[7] Zhuang Changfu, Liu Jianlu, Dai Wen, Wu Zhongping, Wang Ying, Gao Shuang*. Synthesis and Applications in Catalysis of Porphyrinic Metal-Organic Frameworks [J]. Progress in Chemistry, 2014, 26(0203): 277-292.
[8] Wang Zhipeng, Zhang Yan, Wang Xiaoqing*. Models in Metalloenzymes for Dioxygen Activation [J]. Progress in Chemistry, 2013, 25(06): 915-926.
[9] Zhang Yuan, Qi Shihua* . Techniques of Stable Chlorine Isotope Analysis and Relevant Applications in Research of Organochlorine Pollutants [J]. Progress in Chemistry, 2012, 24(12): 2384-2390.
[10] Yuriko Aoki, Feng Long Gu. Elongation Method for Delocalized Nano-wires [J]. Progress in Chemistry, 2012, 24(06): 886-909.
[11] Tang Yayun, Mei Qunbo, Xu Zhijie, Ling Qidan. Application of Porphyrin Compounds in Organic Solar Cells [J]. Progress in Chemistry, 2011, 23(9): 1915-1928.
[12] Yang Shengyan, Wu Zhenyi, Wan Xinjun, Yan Juan. Synthesis of Porphyrin-Fullerene Complexes [J]. Progress in Chemistry, 2011, 23(6): 1123-1136.
[13] Li Zi, Jia Chunyang, Wan Zhongquan. Applications of Porphyrin Derivatives as Dyes for DSSC [J]. Progress in Chemistry, 2011, 23(5): 1014-1021.
[14] Tu Wenwen, Lei Jianping, Ju Huangxian. Nanoassembly and Biosensing of Porphyrins [J]. Progress in Chemistry, 2011, 23(10): 2113-2118.
[15] . Structures and Functions of Metalloporphyrin Protein Conjugates [J]. Progress in Chemistry, 2010, 22(10): 1952-1963.