Porphycene-mediated photooxidation of benzylamines by visible light

被引：65

作者：

Berlicka, Anna ^{[1
]}

Koenig, Burkhard ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany

来源：

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES | 2010年 / 9卷 / 10期

基金：

美国国家科学基金会;

关键词：

CATALYZED AEROBIC OXIDATION; SINGLET OXYGEN; ELECTRON-TRANSFER; SECONDARY-AMINES; PHOTOSENSITIZING PROPERTIES; MOLECULAR-OXYGEN; REDOX PROPERTIES; EFFICIENT; FLAVIN; IMINES;

D O I：

10.1039/c0pp00192a

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A variety of primary and secondary benzylic amines were oxidized efficiently to N-benzylidenebenzylamines and imines, respectively, using 2,7,12,17-tetrapropylporphycene (H2TPrPc) photocatalyst and blue light emitting diodes (LEDs). The photooxidation of 4-methoxybenzylamine in the presence of H2TPrPc and its tin(IV) complex Sn(TPrPc)Cl-2 was studied in detail in order to show that operating mechanisms can be different depending on the photosensitizer type. Two experiments involving solvent deuterium isotope effect and competitive quenching with DABCO provide evidence for the singlet oxygen mechanism as the major pathway in the H2TPrPc-catalyzed reaction and the predominance of the direct electron transfer from the photoexcited dye to the amine when the Sn(TPrPc)Cl-2 complex was used as a photocatalyst.

引用

页码：1359 / 1366

页数：8

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