Synthesis of N-confused Porphyrin Manganese, Iron and Cobalt Complexes and Their Applications
Received date: 2024-02-15
Online published: 2024-04-12
Supported by
National Natural Science Foundation of China(21671068); 2018 local Development Research Center Project of Yichun Univeristy(DF2018021); Science and Technology Research Project of Education Comission of Jiangxi Province(GJJ2201723); Science and Technology Research Project of Education Comission of Jiangxi Province(GJJ2201724); science and technology research project of health commission of Jiangxi province(202212701); Open Fund of Key Laboratory of Green Chemical Technology of Fujian Province University(WYKF-GCT2022-1)
Study on the synthesis and applications of N-confused porphyrin manganese, iron and cobalt complexes has become one of the hot topics of porphyrin chemistry. Compared with the coordination chemistry of porphyrin, that of N-confused porphyrin is complicated because of the peripheral nitrogen atom, the intramolecular C—H bond and NH tautomerism. N-confused porphyrin has two NH tautomers, isomer A and isomer B. Varied functions are observed in the coordination chemistry of N-confused porphyrin such as stabilization of unusual metal oxidation states and metal-carbon bond formation. N-confused porphyrins have flexible character toward the metal oxidation state. Removal of the number of hydrogen atoms from one to three will result in a monanionic, dianionic and trianionic macrocycle. The various metal oxidation states are observed in N-confused porphyrin manganese, iron and cobalt complexes. The monovalent character of N-confused porphyrin is observed in cobalt chemistry such as CoII(2-N-RNCTPP)Cl and CoII(NCTPP). The cobalt metal takes a valence of +2 since CoII(2-N-RNCTPP)Cl has a monoanionic axial ligand and N-confused porphyrin ligand. The squar-planar Co(Ⅱ) complex CoII(NCTPP) exists the cobalt-carbon bond. The divalent and trivalent characters of N-confused porphyrins are observed in manganese, iron and cobalt chemistry. In Mn(Ⅱ) and Fe(Ⅱ) complexes of N-confused porphyrin MnII(NHCTPP)Br and FeII(NHCTPP)Br, oxidation of the metal center is observed through intramolecular C—H bond activation of N-confused porphyrin ligand, which can be converted into Mn(Ⅲ) and Fe(Ⅲ) complexes MnⅢ(NCTPP)Br and FeⅢ(NCTPP)Br on exposure to air in solutions. {FeNO}6 with a linear Fe-NO conformation is observed in the iron chemistry of N-confused porphyrin, which is unusually stable among the porphyrin iron nitrosyl complexes. It implies that iron N-confused porphyrin complexes can be used to study NO delivery and storage. This review covers the progress on the synthesis of N-confused porphyrin manganese, iron and cobalt complexes and their applications in the field of catalytic chemistry and biological chemistry. The synthesis methods of N-confused porphyrin manganese, iron and cobalt complexes and their applications in catalytic oxidation, cyclopropanation of alkene, nitrate reductase activity and chemical nuclease activity are introduced systematically.
Wanhong Li , Yinghong Mu , Xin Wang , Xing Li , Haiyang Liu , Suhong Peng . Synthesis of N-confused Porphyrin Manganese, Iron and Cobalt Complexes and Their Applications[J]. Acta Chimica Sinica, 2024 , 82(5) : 541 -550 . DOI: 10.6023/A24020052
| [1] | Collman, J. P.; Boulatov, R.; Sunderland, C. J.; Fu, L. Chem. Rev. 2004, 104, 561. |
| [2] | Geier, G. R.; Haynes, D. M.; Lindsey, J. S. Org. Lett. 1999, 1, 1455. |
| [3] | Harvey, J. D.; Ziegler, C. J. J. Inorg. Biochem. 2006, 99, 869. |
| [4] | Yu, X. Y.; Liao, Z. X.; Jiang, B. F.; Zheng, L. Y.; Li, X. F. Spectrochim. Acta A 2014, 133, 372. |
| [5] | Fields, K. B.; Engle, J. T.; Sripothongnak, S.; Kim, C.; Zhang, X. P.; Ziegler, C. J. Chem. Commun. 2011, 47, 749. |
| [6] | Yamamoto, T.; Toganoh, M.; Furuta, H. Dalton Trans. 2012, 41, 9154. |
| [7] | Peng, S. H.; Wang, L. L.; Cai, S. S.; Xiao, H. Q.; Zhao, X. T.; Wang, H.; Liu, H. Y. J. Porphyr. Phthalocya. 2022, 26, 195. |
| [8] | Li, W. H.; Yu, M. Y.; Wang, L. L.; Zhu, D. H.; Peng, S. H.; Wang, H.; Liu, H. Y. Acta Chim. Sinica 2023, 81, 345 (in Chinese). |
| [8] | (李万红, 于明月, 王丽丽, 朱德煌, 彭素红, 王惠, 刘海洋, 化学学报, 2023, 81, 345.) |
| [9] | Yu, X. Y.; Liao, Z. X.; Jiang, B. F.; Zheng, L. Y.; Li, X. F. Spectrochim. Acta A 2014, 133, 372. |
| [10] | Thomas, A. P.; Babu, P. S.; Asha, N. S.; Ramakrishnan, S.; Ramaiah, D.; Chandrashekar, T. K.; Srinivasan, A.; Pillai, M. R. J. Med. Chem. 2012, 55, 5110. |
| [11] | Peng, S. H.; Zhou, R.; Zou, H. B. Chinese J. Org. Chem. 2019, 39, 3384 (in Chinese). |
| [11] | (彭素红, 周蓉, 邹怀波, 有机化学, 2019, 39, 3384.) |
| [12] | Toganoh, M.; Furuta, H. Chem. Rev. 2022, 122, 8313. |
| [13] | Deng, F. L.; Ge, X. R.; Deng, Z. Y.; Xu, L.; Rao, Y. T.; Yin, B. S.; Zhou, M. B.; Song, J. X.; Osuka, A. Inorg. Chem. 2024, 63, 5769. |
| [14] | Chung, C. H.; Hsu, K. C.; Lee, H.; Hung, C. H. Chemistry 2019, 77, 379 (in Chinese). |
| [14] | (庄川弘, 许凯淳, 李向, 洪政雄, 化学, 2019, 77, 379.) |
| [15] | Miyazaki, T.; Fukuyama, K.; Mashita, S.; Deguchi, Y.; Yamamoto, T.; Ishida, M.; Mori, S.; Furuta, H. ChemPlusChem 2019, 84, 603. |
| [16] | dela Cruz, J.; Ruamps, S.; Arco, S.; Hung, C. H. Dalton Trans. 2019, 48, 7527. |
| [17] | Ge, Y. S.; Cheng, G. E.; Xu, N. F.; Wang, W. Z.; Ke, H. Z. Catal. Sci. Technol. 2019, 9, 4255. |
| [18] | Hua, W.; Liu, T. T.; Zheng, Z. Y.; Yuan, H. H.; Xiao, L.; Feng, K.; Hui, J. S.; Deng, Z.; Ma, M. T.; Cheng, J.; Song, D. Q.; Lyu, F. L.; Zhong, J.; Peng, Y. Angew. Chem. Int. Ed. 2024, e202315922. |
| [19] | Koniarz, S.; Szyde?ko, K.; Bia?ek, M. J.; Hurej, K.; Chmielewski, P. J. Adv. Sci. 2024, 11, 2306696. |
| [20] | Bohle, D. S.; Chen, W. C.; Hung, C. H. Inorg. Chem. 2002, 41, 3334. |
| [21] | Harvey, J. D.; Zielger, C. J. Chem. Commun. 2002, 1942. |
| [22] | Harvey, J. D.; Zielger, C. J. Chem. Commun. 2003, 2890. |
| [23] | Hung, S. W.; Yang, F. A.; Chen, J. H.; Wang, S. S.; Tung, J. Y. Inorg. Chem. 2008, 47, 7202. |
| [24] | Hasio, D. Z.; Chen, J. H.; Wang, S. S.; Tung, J. Y. Polyhedron 2012, 31, 339. |
| [25] | Yang, C.; Tsai, M. Y.; Hung, S. W.; Chen, J. H.; Wang, S. S.; Tung, J. Y. Polyhedron 2012, 37, 1. |
| [26] | Chen, W. C.; Hung, C. H. Inorg. Chem. 2001, 40, 5070. |
| [27] | Wang, Y. C.; Chen, J. H.; Wang, S. S.; Tung, J. Y. Inorg. Chem. 2013, 52, 10711. |
| [28] | Harvey, J. D.; Ziegler, C. J. Chem. Commun. 2004, 14, 1666. |
| [29] | Zilbermann, I.; Maimon, E.; Ydgar, R.; Shames, A. I.; Korin, E.; Soifer, L.; Bettelheim, A. Inorg. Chem. Commun. 2004, 7, 1238. |
| [30] | Peng, S. H.; Mahmood, M. H. R.; Zou, H. B.; Yang, S. B.; Liu, H. Y. J. Mol. Catal. A: Chem. 2014, 395, 180. |
| [31] | Peng, S. H.; Lv, B. B.; Ali, A.; Wang, J. M.; Ying, X.; Wang, H.; Liu, J. B.; Ji, L. N.; Liu, H. Y. J. Porphyr. Phthalocya. 2016, 20, 624. |
| [32] | Ikawa, Y.; Moriyama, S.; Harada, H.; Furuta, H. Org. Biomol. Chem. 2008, 6, 4157. |
| [33] | Du, Y. H.; Zhang, D.; Chen, W.; Zhang, M.; Zhou, Y. Y.; Zhou, X. Bioorg. Med. Chem. 2010, 18, 1111. |
| [34] | Bigey, P.; S?nnichsen, S. H.; Meunier, B.; Nielsen, P. E. Bioconjug. Chem. 1997, 8, 267. |
| [35] | Lu, J.; Liu, H. Y.; Shi, L.; Wang, S. L.; Ying, X.; Zhang, L.; Ji, L. N.; Zang, L. Q.; Chang, C. K. Chin. Chem. Lett. 2011, 22, 101. |
| [36] | Huang, J. T.; Wang, X. L.; Zhang, Y.; Mahmood, M. H. R.; Huang, Y. Y.; Ying, X.; Ji, L. N.; Liu, H. Y. Transit. Metal Chem. 2013, 38, 283. |
| [37] | Zhang, Y.; Wang, Q.; Wen, J. Y.; Wang, X. L.; Mahmood, M. H. R.; Ji, L. N.; Liu, H. Y. Chin. J. Chem. 2013, 31, 1321. |
| [38] | Hegde, A. H.; Prashanth, S. N.; Seetharamappa, J. J. Pharm. Biomed. Anal. 2012, 63, 40. |
| [39] | Cui, Y. R.; Hao, E. J.; Hui, G. Q.; Guo, W.; Cui, F. L. Spectrochim. Acta A 2013, 110, 92. |
| [40] | Ching, W. M.; Chuang, C. H.; Wu, C. W.; Peng, C. H.; Hung, C. H. J. Am. Chem. Soc. 2009, 131, 7952. |
| [41] | Ching, W. M.; Chen, P. P. Y.; Hung, C. H. Dalton Trans. 2017, 46, 15087. |
| [42] | Iwanaga, O.; Miyanishi, M.; Tachibana, T.; Miyazaki, T.; Shiota, Y.; Yoshizawa, K.; Futura, H. Molecules 2022, 27, 7266. |
| [43] | Miyazaki, T.; Yamamoto, T.; Mashita, S.; Deguchi, Y.; Fukuyama, K.; Ishida, M.; Mori, S.; Furuta, H. Eur. J. Inorg. Chem. 2018, 2, 203. |
| [44] | Chuang, C. H.; Liaw, W. F.; Hung, C. H. Angew. Chem. Int. Ed. 2016, 55, 5190. |
| [45] | Sun, M.; Xie, Y. S.; Baryshr, G.; Wu, X. Y.; ?gren, H.; Li, S. J. Chem. Sci. 2024, 15, 2047. |
| [46] | Li, Q. H.; Ishida, M.; Wang, Y. Y.; Sha, F.; Wu, X. Y.; ?gren, H.; Furuta, H.; Xie, Y. S. Angew. Chem. Int. Ed. 2023, 62, e202212174. |
| [47] | Li, C. J.; Li, Q. Z.; Shao, J. W.; Tong, Z. F.; Furuta, H.; Xie, Y. S. J. Am. Chem. Soc. 2020, 142, 17195. |
| [48] | Su, G. X.; Li, Q. Z.; Ishida, M.; Li, C. J.; Sha, F.; Wu, X. Y.; Wang, L.; Baryshnikov, G.; Li, D. W.; ?gren, H.; Furuta, H.; Xie, Y. S. Angew. Chem. Int. Ed. 2020, 59, 1537. |
| [49] | Ren, Z. X.; Zhao, B.; Xie, J. Small 2023, 19, 2301818. |
| [50] | Li, Q. Z.; Li, C. J.; Baryshnikov, G.; Ding, Y. B.; Zhao, C. X.; Gu, T. T.; Sha, F.; Liang, X.; Zhu, W. H.; Wu, X. Y.; ?gren, H.; Sessler, J. L.; Xie, Y. S. Nature Commun. 2020, 11, 5289. |
/
| 〈 |
|
〉 |
