Synthesis, Reactivity, and Spectroscopic Properties of meso-Triaryl-5-oxaporphyrins

被引:15
|
作者
Kakeya, Kazuhisa
Nakagawa, Aya
Mizutani, Tadashi [1 ]
Hitomi, Yutaka
Kodera, Masahito
机构
[1] Doshisha Univ, Fac Sci & Engn, Dept Mol Chem & Biochem, Kyotanabe, Kyoto 6100321, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 15期
关键词
HELICAL CHIRALITY INDUCTION; COUPLED OXIDATION; VERDOHEME ANALOGS; PLANAR MACROCYCLE; 5-OXAPORPHYRIN COMPLEXES; RESONANCE RAMAN; HEME; PORPHYRINS; MECHANISM; SPECTRA;
D O I
10.1021/jo3010342
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[meso-Triaryl-21,23-didehydro-23H-5-oxaporphyrinato](trifluoroacetato)zinc(II) was prepared by the reaction of meso-triarylbilindione with acetic anhydride and zinc acetate, and it was isolated as a trifluoroacetate salt. The X-ray crystallographic study demonstrated that the trifluoroacetate anion was coordinated to the zinc ion. [21,23-Didehydro-10,15,20-tris(4-methoxycarbonylphenyl)-23H-5-oxaporphyrinato]trifluoroacetato)zinc(II) 3a was dissolved in various organic solvents such as toluene, chloroform, diethyl ether, ethyl acetate, acetone, acetonitrile, methanol, DMSO, and DMF, although it readily reacted with alcohols and DMF to yield linear tetrapyrroles. The solubility of 3a in toluene was 4.2 +/- 0.1 g dm(-3) at room temperature. 3a showed characteristic UV-vis absorption at 649 nm and fluorescence emission at 657 nm in chloroform. The fluorescence quantum yields of 3a, [21,23-didehydro-10,15,20-triphenyl-23H-5-oxaporphyrinato]-(trifluoroacetato)zinc(II) (3c), and [21,23-didehydro-10,15,20-tris(4-methoxyphenyl)-23H-5-oxaporphyrinato]-(trifluoroacetato)zinc(II) (3b) were 0.071, 0.071, and 0.050, respectively. Reaction of 3a with EtOH afforded the zinc complex of 19-ethoxybilinone, and it proceeded 2 orders of magnitude faster than that of [beta-octaalkyl-21,23-didehydro-23H-5-oxaporphyrinato]zinc(II). The reaction with alcohols was sensitive to steric bulk of the alcohols; the rate of reaction with i-PrOH was 2700 times faster than that of t-BuOH at 303 K. The reaction of [meso-triaryl-21,23-didehydro-23H-5-oxaporphyrinato]-zinc(II) with water proceeded 3 orders of magnitude slower than that with EtOH.
引用
收藏
页码:6510 / 6519
页数:10
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