阴、阳离子型水溶性卟啉的有效合成
收稿日期: 2017-02-25
修回日期: 2017-04-12
网络出版日期: 2017-05-02
基金资助
河南省高等学校重点科研项目计划(No.16A150012)、河南师范大学青年科学基金(No.214QK15)、河南师范大学博士科研启动基金(No.qd15113)资助项目.
Efficient Synthesis of Anionic and Cationic Water-Soluble Porphyrins
Received date: 2017-02-25
Revised date: 2017-04-12
Online published: 2017-05-02
Supported by
Project supported by the Key Program for High School of Henan Province (No. 16A150012) and the Science Foundation for Young Scholar of Henan Normal University (No. 214QK15) and the Doctoral Science Research Foundation of Henan Normal University (No. qd15113).
常毅 , 刘梦阳 , 牛梦园 . 阴、阳离子型水溶性卟啉的有效合成[J]. 有机化学, 2017 , 37(9) : 2442 -2448 . DOI: 10.6023/cjoc201702035
A kind of cationic water-soluble porphyrin containing pyridinium group and a kind of anionic water-soluble porphyrin containing sulfonic group were synthesized efficiently according to the chosen conditions. During the synthesis process, 5,10,15,20-tetra(pyridin-4-yl)porphyrin and 5,10,15,20-tetra-phenol porphyrin were chosen as the precursors, while triethylene glycol monomethyl ether and manganese were introduced on porphyrin as the functional group. These procedures have the advantages of operation simplicity, high yields, mild conditions, and provide a good method for the synthesis of similar types of water soluble porphyrins at the same time.
Key words: water-soluble; porphyrins; manganese porphyrin; substituents; synthesis; modification
[1] Sessler, J. L.; Tomat, E. Acc. Chem. Res. 2007, 40, 371.
[2] (a) McConnell, A. J.; Wood, C. S.; Neelakandan, P. P.; Nitschke, J. R. Chem. Rev. 2015, 115, 7729.
(b) Tanaka, T.; Osuka, A. Chem. Soc. Rev. 2015, 44, 943.
(c) Chang, Y.; Michelin, C.; Bucher, L.; Desbois, N.; Gros, C. P.; Piant, S.; Bolze, F.; Fang, Y.-Y.; Jiang, X.-Q.; Kadish, K. M. Chem. Eur. J. 2015, 21, 12018.
(d) Liang, P.-X.; Mi, Y.-S.; Duan, J.-S.; Yang, Z.; Wang, D.; Cao, H.; He, W.-L.; Yang, H. Chin. J. Chem. 2016, 34, 381.
[3] (a) Wang, Y.-Q.; Chen, B.; Wu, W.-J.; Li, X.; Zhu, W.-H.; Tian, H.; Xie, Y.-S. Angew. Chem., Int. Ed. 2014, 53, 10779.
(b) Xie, Y.-S.; Tang, Y.-Y.; Wu, W.-J.; Wang, Y.-Q.; Liu, J.-C.; Li, X.; Tian, H.; Zhu, W.-H. J. Am. Chem. Soc. 2015, 137, 14055.
(c) Gu, C.-Z.; Meng, S.-X.; Feng, Y.-Q. Chin. J. Org. Chem. 2015, 35, 1229(in Chinese). (顾承志, 孟舒献, 冯亚青, 有机化学, 2015, 35, 1229.)
(d) Lu, J.-M.; Cai, W.-Q.; Zhang, G.-C.; Liu, S.-J.; Lei, Y.; Fei, H. Acta Chim. Sinica 2015, 73, 1153(in Chinese). (卢俊明, 蔡万清, 张桂传, 刘升建, 应磊, 黄飞, 化学学报, 2015, 73, 1153.)
[4] (a) Ding, Y.-B.; Zhu, W.-H.; Xie, Y.-S. Chem. Rev. 2017, 117, 2203.
(b) Ding, Y.-B.; Tang, Y.-Y.; Zhu, W.-H.; Xie, Y.-S. Chem. Soc. Rev. 2015, 44, 1101-1112.
[5] (a) To, C.-T.; Yang, W.; Chan, K.-S. Chin. J. Chem. 2016, 34, 955.
(b) Xu, Y.; Zhang, H.-Z.; Wang, X.-Y.; Liu, G.-Y. Chin. J. Chem. 2015, 33, 1393.
(c) Ren, Q.-G.; Zhou, X.-T.; J, H.-B. Chin. J. Org. Chem. 2010, 30, 1605(in Chinese). (任清刚, 周贤太, 纪红兵, 有机化学, 2010, 30, 1605.)
[6] (a) Meunier, B.; de Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104, 3947.
(b) Dydio, P.; Key, H. M.; Nazarenko, A.; Rha1, J. Y.-E.;Seyedkazemi1, V.; Clark, D. S.; Hartwig, J. F. Science 2016, 354, 102.
[7] (a) Dolmans, D. E. J. G. J.; Fukumura, D.; Jain, R. K. Nat. Rev. Cancer 2003, 3, 380.
(b) Lu, K.-D.; He, C.-B.; Lin, W.-B. J. Am. Chem. Soc. 2015, 137, 7600.
(c) Schmitt, J.; Heitz, V.; Sour, A.; Bolze, F.; Ftouni, H.; Nicoud, J.-F.; Flamigni, L.; Ventura, B. Angew. Chem., Int. Ed. 2015, 54, 169.
(d) Long, S.-R.; Wan, Y.; Xia, A.-D. Acta Chim. Sinica 2015, 73, 723(in Chinese). (龙飒然, 宛岩, 夏安东, 化学学报, 2015, 73, 723.)
[8] Singh, S.; Aggarwal, A.; Bhupathiraju, N. V. S. D. K.; Arianna, G.; Tiwari, K.; Drain, C. M. Chem. Rev. 2015, 115, 10261.
[9] (a) Bonnett, R. Chem. Rev. 1995, 24, 415.
(b) Almarsson, O.; Adalsteinsson, H.; Bruice, T. C. J. Am. Chem. Soc. 1995, 117, 4524.
[10] Pratviel, G. Coord. Chem. Rew. 2016, 308, 460.
[11] Todd, D. J.; Kay, J. Annu. Rev. Med. 2016, 67, 273.
[12] Yang, J.-J.; Yang, J.-H.; Wei, L.-X.; Zuikiya, O.; Yang, W.; Li, S.-Y.; Zou, J.; Maniccia, A. W.; Mao, H.; Zhao, F.-Q.; Malchow, R.; Zhao, S.-M.; Johnson, J.; Hu, X.-P.; Krogstad, E.; Liu, Z.-R. J. Am. Chem. Soc. 2008, 130, 9260.
[13] Wang, L.-Y.; Cao, D.-R. Chin. J. Org. Chem. 2012, 32, 2248(in Chinese). (汪凌云, 曹德榕, 有机化学, 2012, 32, 2248.)
[14] Laguerre, A.; Chang, Y.; Pirrotta, M.; Desbois, N.; Gros, C. P.; Lesniewska, E.; Monchaud, D. Org. Biomol. Chem. 2015, 13, 7034.
[15] Dong, R.-J.; Bo, Y.; Tong, G.-S.; Zhou, Y.-F.; Zhu, X.-Y.; Lu, Y.-F. Nanoscale 2014, 6, 4544.
[16] Zhou, X.-T.; Ren, G.-Q.; Ji, H.-B. J. Porphyrins Phthalocyanines 2013, 17, 1104.
[17] Mori, S.; Ishii, K.; Hirakawa, Y.; Nakamura, R.; Hashimoto, K. Inorg. Chem. 2011, 50, 2037.
[18] Gouterman, M. In The Porphyrins, Vol. 3, Ed.:Dolphin, D., Academic Press, New York, 1978, Part A, pp. 1~165.
[19] Adler, A. D.; Longo, F. R. J. Org. Chem. 1967, 32, 476.
[20] Sreejith, S.; Joseph, J.; Lin, M.-J.; Menon, N. V.; Borah, P.; Ng, H.-J.; Loong, Y. X.; Kang, Y.-J.; Yu, S. W.-K.; Zhao, Y.-L. ACS Nano 2015, 9, 5695.
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