JAPC  >> Vol. 5 No. 4 (November 2016)

    卟啉类衍生物合成与应用的研究进展
    Progress in Synthesis of Porphyrin Derivatives and Its Application

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作者:  

胡薏冰,黄江波:湖南省中医药研究院,湖南 长沙 ;
丁 睿,丁志坚:桂林晖昂生化药业有限责任公司,广西 桂林 ;
彭红建:中南大学化学化工学院,湖南 长沙

关键词:
卟啉类衍生物合成应用Porphyrin Derivative Synthesis Application

摘要:

卟啉类衍生物由于共轭平面结构具有良好的光谱学性能和电化学性能,在临床医学、材料科学及生物学等诸多领域有着异常广泛的应用,其研究与开发日益活跃,引起越来越多科学工作者的关注。本文综述了卟啉类衍生物的合成与应用的研究现状和进展,并为今后卟啉类衍生物合成与设计指明了方向。

Porphyrin derivatives have a very wide-range application in the clinical medicine, materials science and biology and other fields because it has good spectroscopic property and electrochemical performance due to its conjugate plane structure. Its research and development have become increasingly active, attracting more and more attention. In this paper, the present status and progress of the synthesis and application of porphyrin derivatives are reviewed, and the direction is pointed out for the synthesis and designation of porphyrin derivatives.

文章引用:
胡薏冰, 丁睿, 丁志坚, 黄江波, 彭红建. 卟啉类衍生物合成与应用的研究进展[J]. 物理化学进展, 2016, 5(4): 122-130. http://dx.doi.org/10.12677/JAPC.2016.54014

参考文献

[1] Watanabe, E., Nishimura, S., Ogoshi, H., et al. (1975) Orientation of Electrophilic Meso-Substitution in Metallooctaethylporphyrins. Tetrahedron, 31, 1385-1390. https://doi.org/10.1016/0040-4020(75)87068-2
[2] Hoffmann, M.R., Martin, S.T., Choi, W.Y., et al. (1995) Environmental Applications of Semiconductor Photocatalysis. Chemical Reviews, 95, 69-96. https://doi.org/10.1021/cr00033a004
[3] Zhou, X., Tse, M.K., Wan, T.S.M., et al. (1996) Synthesis of Beta-Mono-, Tetra-, and Octa-Substituted Sterically Bulky Porphyrins via Suzuki cross Coupling. Journal of Organic Chemistry, 61, 3590-3593. https://doi.org/10.1021/jo952205+
[4] Sedghi, G., Sawada, K., Esdaile, L.J., et al. (2008) Single Molecule Conductance of Porphyrin Wires with Ultralow Attenuation. Journal of the American Chemical Society, 130, 8582-8583. https://doi.org/10.1021/ja802281c
[5] Liu, X.-G., Feng, Y.-Q., Chen, X., et al. (2005) Porphyrins as Dipolarophiles in 1, 3-Dipolar Cycloaddition Reactions with Nitrile Oxide. SYNLETT, 6, 1030-1032.
[6] Rothemund, P. (1939) Porphyrin Studies III: The Structure of the Porphine Ring System. Journal of the American Chemical Society, 61, 2912-2915. https://doi.org/10.1021/ja01265a096
[7] Arsenault, G.P., Bullock, E. and MacDonald, S.F. (1960) Pyrromethanes and Porphyrins Therefrom. Journal of the American Chemical Society, 82, 4384-4389. https://doi.org/10.1021/ja01501a066
[8] Adler, A.D., Longo, F.R., John, D.F., et al. (1967) A Simplified Synthesis for Meso-Tetraphenylporphine. Journal of Organic Chemistry, 32, 476-476. https://doi.org/10.1021/jo01288a053
[9] Broadhurst, M.J., Grigg, R. and Johnson, A.W. (1971) Synthesis of Porphyrin Analogues Containing Furan and or Thiophen Rings. Journal of the American Chemical Society, 95, 3681-3690.
[10] Boudif, A. and Momenteau, M. (1996) A New Convergent Method for Porphyrin Synthesis Based on a “3 + 1” Condensation. Journal of the Chemical Society, Perkin Transactions, 1, 1235-1242. https://doi.org/10.1039/P19960001235
[11] Senge, M.O. (2003) Synthetic Access to 5,10-Disubstituted Porphyrins. Tetrahedron Letters, 44, 157-160. https://doi.org/10.1016/S0040-4039(02)02475-9
[12] Lash, T.D. (1997) Porphyrins with Exocyclic Rings. Part 9 [1] Synthesis of Porphyrins by the “3+1” Approach. Journal of Porphyrins and Phthalocyanines, 1, 29-44. https://doi.org/10.1002/(SICI)1099-1409(199701)1:1<29::AID-JPP7>3.0.CO;2-S
[13] Lindsey, J.S, Schreiman, I.C., Hsu, H.C. et al. (1987) Rothemund and Adler-Longo Reactions Revisited Synthesis of Tetraphenylporphyrins under Equilibrium Conditions. Journal of Organic Chemistry, 52, 827-836. https://doi.org/10.1021/jo00381a022
[14] Montanari, F. and Casella, L. (1994) Metalloporphyrins Catalyzed Oxidations. Springer, Berlin. https://doi.org/10.1007/978-94-017-2247-6
[15] Dolphin, D. (1970) Porphyrinogens and Porphodimrthenes, Intermediates in the Synthesis of Meso-Tetraphenyl Porphins from Pyrroles and Benzaldehyde. Journal of Heterocyclic Chemistry, 7, 275-282. https://doi.org/10.1002/jhet.5570070205
[16] Gedye, R., Smith, F. and Westaway, K. (1986) The Use of Microwave Ovens for Rapid Organic Synthesis. Tetrahedron Letters, 27, 279-282. https://doi.org/10.1016/S0040-4039(00)83996-9
[17] Petit, A., Loupy, A., Maillard, P., et al. (1992) Microwave Irradiation in Dry Media: A New and Easy Method for Synthesis of Tetrapyrrolic Compounds. Synthetic Communications, 22, 1137-1142. https://doi.org/10.1080/00397919208021097
[18] 胡希明, 梅治乾, 刘海洋, 等. 四苯基卟啉的微波诱导合成研究[J]. 华南理工大学学报(自然科学版), 1999, 27(10): 11-15.
[19] 刘云, 徐同宽, 肖德宝, 等. 四苯基卟啉的催化合成和微波合成研究[J]. 北京轻工业学院学报, 1998, 16(4): 37- 44.
[20] 黄兴强, 樊艳玲, 吴天骄, 吴腊梅, 陈连清. 微波辐射下催化合成四(对硝基苯基)卟啉[J]. 江西师范大学学报(自然科学版), 2009, 33(6): 721-724.
[21] Benjamin, B., Faugeras, P.A., Vergnaud, J., et al. (2010) Iodine-Catalyzed One-Pot Synthesis of Unsymmetrical Meso- Substituted Porphyrins, Tetrahedron, 66, 1994-1996. https://doi.org/10.1016/j.tet.2010.01.055
[22] 陈创, 徐扬, 胡芸, 吴璟, 陈金阳, 等. 系列氰基卟啉化合物的微波合成及表征[J]. 广州化工, 2013, 41(14): 70- 71.
[23] 陈年友, 赵胜芳, 陈国安. 一种新型卟啉-蒽醌化合物的微波合成及其光诱导电子转移性质[J]. 化学试剂, 2013, 35(1): 24-26.
[24] 孙福强, 梅文杰, 崔英德. 微波辅助合成5-[4-(4-溴代丁氧基)苯基]-10,15,20-三对甲氧基苯基卟啉[J]. 化工进展, 2014, 33(5): 1296-1299.
[25] Hasrat, A. and Johan, E.V. (1999) Metal Complexes as Photo- and Radiosensitizers. Chemical Reviews, 99, 2379-2450. https://doi.org/10.1021/cr980439y
[26] Comuzzi, C., Cogoi, S., Overhand, M., et al. (2006) Synthesis and Biological Evaluation of New Pentaphyrin Macrocycles for Photodynamictherapy. Journal of Medicinal Chemistry, 49, 196-204. https://doi.org/10.1021/jm050831l
[27] Desroches, M.-C., Bautista-Sanchez, A., Lamotte, C., et al. (2006) Pharmaco-kinetics of a Tri-Glucoconjugated 5, 10, 15-(Meta)-Trihydroxyphenyl-20-Phenyl Porphyrin Photosensitizer for PDT a Single Dose Study in the Rat. Journal of Photochemistry and Photobiology B: Biology, 85, 56-64. https://doi.org/10.1016/j.jphotobiol.2006.03.008
[28] Lang, K., Mosinger, J. and Wagnerova, D.M. (2004) Photo-physical Properties of Porphyrinoid Sensitizers Non-Cova- lently Bound to Hostmolecules. Models for Photo Dynamic Therapy. Coordination Chemistry Reviews, 248, 321-350. https://doi.org/10.1016/j.ccr.2004.02.004
[29] Dolmans, D.E.J.G.J., Fukumura, D. and Jain, R.K. (2003) Photodynamic Therapy for Cancer. Nature Reviews Cancer, 3, 380-387. https://doi.org/10.1038/nrc1071
[30] 丁志坚, 韩臻, 周春秋, 等. 一种新型的完全水溶的光敏剂单体及其制备方法及应用[P]. 中国专利, 104086554A. 2014-10-08.
[31] Baldo, M.A., Obrien, D.F., You, Y., et al. (1998) Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices. Nature, 395, 151-154. https://doi.org/10.1038/25954
[32] Zhang, X.H., Xie, Z.Y., Wu, F.P., et al. (2003) Red Electroluminescence and Photolu-Minescence Properties of New Porphyrin Compounds. Chemical Physics Letters, 382, 561-566. https://doi.org/10.1016/j.cplett.2003.10.104
[33] Burrows, P.E., Forest, S.R., Sibley, S.P., et al. (1996) Color-Tunable Organic Light-Emitting Devices. Applied Physics Letters, 69, 2959-2961. https://doi.org/10.1063/1.117743
[34] Sakakibara, Y., Okutsu, S., Enokida, T., et al. (1999) Red Organic Electroluminescence Devices with a Reduced Porphyrin Compound, Tetraphenylchlorin. Applied Physics Letters, 74, 2587-2589. https://doi.org/10.1063/1.123906
[35] Rault, B.J., Paul, R.C., Simonneaux, G.J. (2008) Comparative Be-haviour of the Anodic Oxidation of Mono-, Di- and Tetra-Arylporphyrins: Towards New Electroactive Materials with Variable Bandgaps. Electroanalytical Chemistry, 623, 204-214. https://doi.org/10.1016/j.jelechem.2008.07.013
[36] 徐海云, 胡春华, 冯翠兰. 卟啉类有机化合物在染料敏化太阳能电池的应用研究进展[J]. 应用化工, 2011, 40(8): 1451-1457.
[37] 张天慧, 朴玲钰, 赵谡玲, 等. 有机太阳能电池材料研究新进展[J]. 有机化学, 2011, 31(2): 260-272.
[38] Deviprasad, G.R. and D’Souza, F. (2000) Molecular Recognition Directed Porphyrin Chemosensor for Selective Detection of Nicotine and Cotinine. Chemical Communications, 19, 1915-1916. https://doi.org/10.1039/b006055k
[39] Armitage, B. (1998) Photocleavage of Nucleic Acids. Chemical Reviews, 98, 1171-1200. https://doi.org/10.1021/cr960428+