m-Benziporphyrin(1.1.0.0)s as a Rare Example of Ring-Contracted Carbaporphyrins with Metal-Coordination Ability: Distorted Coordination Structures and Small HOMO-LUMO Gaps

被引:8
|
作者
Liu, Le [1 ]
Zhang, Fenni [1 ]
Xu, Ling [1 ]
Zhou, Mingbo [1 ]
Yin, Bangshao [1 ]
Tanaka, Takayuki [2 ]
Osuka, Atsuhiro [1 ]
Song, Jianxin [1 ]
机构
[1] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med, Key Lab Assembly & Applicat Organ Funct Mol Hunan, Minist Educ China,Coll Chem & Chem Engn, Changsha 410081, Peoples R China
[2] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
基金
中国国家自然科学基金;
关键词
carbaporphyrin; dimer; Pd metalation; porphyrinoid ring-contracted porphyrin; Suzuki-Miyaura coupling; BENZIPORPHYRIN; COMPLEXES; PORPHYRIN;
D O I
10.1002/chem.202203517
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
m-Benziporphyrin(1.1.0.0) and mpyreniporphyrin(1.1.0.0) were prepared as ring-contracted carbaporphyrins. While m-Benziporphyrin(1.1.0.0) was unstable, m-pyreniporphyrin(1.1.0.0) was fairly stable. Both of their Pd-II complexes showed distorted coordination structures with extremely short Pd C bonds. As compared with the reported m-benziporphyrin Pd-II complexes, these Pd-II complexes showed considerably small HOMO-LUMO gaps, despite their smaller molecular size. Pd-II metalation of the mpyreniporphyrin(1.1.0.0) dimer gave the corresponding Pd-II complex, which showed similar distorted coordination and a smaller HOMO-LUMO gap. Finally, Pd-II metalation of a pyrenesharing formal p-benziporphyrin(1.1.1.1) dimer gave a nonaromatic Pd-II dimer, which rearranged to an aromatic Pd-II complex upon treatment with alumina.
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页数:8
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