N-错位卟啉锰、铁和钴配合物的合成及其应用

doi:10.6023/A24020052

化学学报 ›› 2024, Vol. 82 ›› Issue (5): 541-550.DOI: 10.6023/A24020052 上一篇下一篇

综述

N-错位卟啉锰、铁和钴配合物的合成及其应用

李万红^a, 穆应红^a, 王新^a, 李星^a, 刘海洋^b, 彭素红^a^,^*()

a 宜春学院化学与生物工程学院宜春 336000
b 华南理工大学化学系广州 510641

投稿日期:2024-02-15 发布日期:2024-04-11

作者简介:

李万红, 就读于宜春学院化学与生物工程学院, 2021级药学专业硕士生, N-错位卟啉金属配合物的合成及应用研究.

穆应红, 就读于宜春学院化学与生物工程学院, 2023级药学专业硕士生, N-错位卟啉金属配合物的合成及应用研究.

王新, 就读于宜春学院化学与生物工程学院, 2020级化学专业本科生, N-错位卟啉金属配合物的合成及应用研究.

李星, 就读于宜春学院化学与生物工程学院, 2017级应用化学本科生, N-错位卟啉金属配合物的合成及应用研究.

刘海洋, 1997年博士毕业于中山大学化学专业, 现任华南理工大学化学与化工学院教授. 广东省高等学校“千百十工程”第三批培养对象. 广东省化学会无机化学专业委员会委员. 长期致力于金属卟啉类大环化合物的催化, 光动力抗肿瘤, 超快速光物理化学过程, 电催化材料与燃料电池研究.

彭素红, 2016年博士毕业于华南理工大学无机化学专业. 现任宜春学院化学与生物工程学院副教授. 主要研究方向为N-错位卟啉金属配合物的合成及应用研究.

基金资助:
国家自然科学基金(21671068); 宜春学院2018地方发展研究中心项目(DF2018021); 江西省教育厅科学技术项目(GJJ2201723); 江西省教育厅科学技术项目(GJJ2201724); 江西省卫生健康委科技计划项目(202212701); 绿色化工技术福建省高校重点实验室开放基金(WYKF-GCT2022-1)

Synthesis of N-confused Porphyrin Manganese, Iron and Cobalt Complexes and Their Applications

Wanhong Li^a, Yinghong Mu^a, Xin Wang^a, Xing Li^a, Haiyang Liu^b, Suhong Peng^a()

a College of Chemsitry and Bioengineering, Yichun University, Yichun 336000, China
b Department of Chemistry, South China University of Technology, Guangzhou 510641, China

Received:2024-02-15 Published:2024-04-11
Contact: *E-mail: shpeng1987@163.com
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)

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摘要/Abstract

N-错位卟啉锰、铁和钴配合物的合成与应用研究已成为当今卟啉化学的前沿课题之一. 本文综述了N-错位卟啉锰、铁和钴配合物的合成及其在催化化学和生物化学等领域的研究进展, 系统介绍了N-错位卟啉锰、铁和钴配合物的合成及其在催化烯烃氧化、环丙烷化、亚硝酸根还原酶和化学核酸酶等领域的应用.

关键词: N-错位卟啉锰、铁和钴配合物, 合成, 应用

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 Co^II(2-N-RNCTPP)Cl and Co^II(NCTPP). The cobalt metal takes a valence of +2 since Co^II(2-N-RNCTPP)Cl has a monoanionic axial ligand and N-confused porphyrin ligand. The squar-planar Co(Ⅱ) complex Co^II(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 Mn^II(NHCTPP)Br and Fe^II(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 Mn^Ⅲ(NCTPP)Br and Fe^Ⅲ(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.

Key words: N-confused porphyrin manganese, iron and cobalt complexes, synthesis, application

引用此文

李万红, 穆应红, 王新, 李星, 刘海洋, 彭素红. N-错位卟啉锰、铁和钴配合物的合成及其应用[J]. 化学学报, 2024, 82(5): 541-550.

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.

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图/表 19

图1. 四苯基N-错位卟啉NCTPP的异构体isomer A与isomer B的分子结构

Figure 1. Molecular structures of isomer A and isomer B of tetraphenyl N-confused porphyrin

配合物	反应条件	产率
Mn^II(NHCTPP)Br	氮气保护下, 以乙腈和四氢呋喃的混合溶剂作为反应溶剂, 以四苯基N-错位卟啉与溴化锰为原料, 再加入二甲基吡啶, 回流反应.	82%
Mn^III(2-N-RNCTPP)Br	空气条件下, 以二氯甲烷与甲醇的混合溶液作为反应溶剂, 2-N-烷基四苯基N-错位卟啉与溴化锰回流反应.	61%
Fe^II(NHCTPP)Br	无氧条件下, 以乙腈和四氢呋喃的混合溶剂作为反应溶剂, 以四苯基N-错位卟啉与溴化亚铁为原料, 再加入二甲基吡啶, 回流反应.	85%
Co^II(2-N-RNCTPP)Cl	空气条件下, 以乙腈和甲苯的混合溶剂作为反应溶剂, 加入N-烷基化的N-错位卟啉与六水合氯化钴, 回流反应.	26%

表1. N-错位卟啉锰、铁和钴配合物的合成

Table 1. Synthesis of N-confused porphyrin manganese, iron and cobalt complexes

图2. N-错位卟啉锰配合物的合成路线

Figure 2. Synthetic route of N-confused porphyrin manganese complexes

图3. MnII(NHCTPP)Br与MnIII(NCTPP)Br的紫外可见吸收光谱

Figure 3. UV-visible spectra of MnII(NHCTPP)Br and MnIII(NCTPP)Br

图4. MnII(NHCTPP)Br和MnIII(NCTPP)Br的晶体结构

Figure 4. Crystal structures of MnII(NHCTPP)Br and MnIII(NCTPP)Br

图5. 2-N-烷基四苯基N-错位卟啉锰配合物的合成路线

Figure 5. Synthetic route of 2-N-alkyl tetraphenyl N-confused porphyrin manganese complexes

图6. N-错位卟啉铁(II)配合物[FeII(NHCTPP)Br]和N-错位卟啉铁(III)配合物[FeIII(NCTPP)Br]的合成路线

Figure 6. Synthetic route of N-confused porphyrin iron(II) complexes [FeII(NHCTPP)Br] and N-confused porphyrin iron(III) complexes [FeIII(NCTPP)Br]

图7. FeII(NHCTPP)Br和 FeIII(NCTPP)Br的晶体结构

Figure 7. Crystal structures of FeII(NHCTPP)Br and FeIII(NCTPP)Br

图8. N-错位卟啉钴(III)配合物CoIII(NCTPP)(H2O)的合成路线

Figure 8. Synthetic route of N-confused porphyrin cobalt(III) complex CoIII(NCTPP)(H2O)

图9. CoIII(NCTPP)(H2O)和CoIII(NCTPP)py2的晶体结构

Figure 9. Crystal structures of CoIII(NCTPP)(H2O) and CoIII(NCTPP)py2

图10. N-错位卟啉钴(II)配合物CoII(NCTPP)的合成路线

Figure 10. Synthetic route of N-confused porphyrin cobalt(II) complex CoII(NCTPP)

图11. N-错位卟啉钴(II)配合物CoII(NCTPP)py和N-错位卟啉钴(III)配合物CoIII(NCTPP)py2的合成路线

Figure 11. Synthetic route of N-confused porphyrin cobalt(II) complexes CoII(NCTPP)py and N-confused porphyrin cobalt(III) complexes CoIII(NCTPP)py2

图12. N-错位卟啉氯化钴(II)配合物CoII(2-N-RNCTPP)Cl的合成路线

Figure 12. Synthetic route of N-confused porphyrin cobalt(II) chloride complexes

图13. N-错位卟啉锰配合物MnIII(2-N-CH3-NCTArP)Cl的分子结构

Figure 13. Molecular structures of N-confused porphyrin manganese complexes MnIII(2-N-CH3-NCTArP)Cl

图14. 四苯基N-错位卟啉铁配合物{FeNO}6和{FeNO}7的分子结构

Figure 14. Molecular structures of iron tetraphenyl N-confused porphyrin complexes {FeNO}6 and {FeNO}7

图15. CoII(NCTPP)py和CoII(2-N-CH3NCTPP)py的分子结构

Figure 15. Molecular structures of CoII(NCTPP)py and CoII(2-N-CH3NCTPP)py

Catalyst(mol%)	n_Styrene/ n_EDA	Temp./ Time	Yield	trans/cis
Co^IITPP(0.5)	5/1	r.t./1 h	6%	72/28
Co^IITPP(1)	1/1.2	80 ℃/20 h	67%	74/26
Co^II(NCTPP)py(1)	1/1.2	80 ℃/20 h	35%	98/2
Co^II(2-N-CH₃NCTPP) py(1)	1/1.2	80 ℃/20 h	51%	98/2
	1/1.2	r.t./20 h	85%	93/7
	5/1	80 ℃/20 h	76.5%	91/9
Co^II(2-N-CH₃NCTPP) py(0.5)	5/1	r.t./1 h	31%	92/8
7(0.5)	5/1	80 ℃/6 h	70%	83/17
7-_red(0.1)	5/1	r.t./1 h	39%	89/11
7-_red(0.5)	5/1	r.t./1 h	80%	92/8
8_-red(0.5)	5/1	r.t./1 h	76%	90/10

表2. N-错位卟啉钴配合物催化苯乙烯环丙烷化反应活性

Table 2. Catalytic activities of N-confused cobalt porphyrin complexes on the cyclopropanation of styrene

图16. N-错位卟啉钴(III)配合物7和8的分子结构

Figure 16. Molecular structures of cobalt(III) N-confused porphyrin complexes 7 and 8

图17. N-错位卟啉钴配合物{Co(NO)}8和{Co(NO)}9的分子结构

Figure 17. Molecular structures of cobalt N-confused porphyrin complexes {Co(NO)}8 and {Co(NO)}9

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N-错位卟啉锰、铁和钴配合物的合成及其应用

Synthesis of N-confused Porphyrin Manganese, Iron and Cobalt Complexes and Their Applications

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