On the synthesis of functionalized porphyrins and porphyrin conjugates via β-aminoporphyrins

被引：47

作者：

Abdulaeva, Inna A. ^{[1
,2
]}

Birin, Kirill P. ^{[2
]}

Michalak, Julien ^{[1
]}

Romieu, Anthony ^{[1
,3
]}

Stern, Christine ^{[1
]}

Bessmertnykh-Lemeune, Alla ^{[1
]}

Guilard, Roger ^{[1
]}

Gorbunova, Yulia G. ^{[2
,4
]}

Tsivadze, Aslan Yu. ^{[2
,4
]}

机构：

[1] Univ Bourgogne Franche Comte, CNRS, UMR 6302, Inst Chim Mol,Univ Bourgogne, 9 Ave Alain Savary, F-21078 Dijon, France

[2] Russian Acad Sci, Frumkin Inst Phys Chem & Electrochem, Leninsky Pr 31-4, Moscow 119071, Russia

[3] Inst Univ France, 103 Blvd St Michel, F-75005 Paris, France

[4] Russian Acad Sci, Kurnakov Inst Gen & Inorgan Chem, Leninsky Pr 31, Moscow 119991, Russia

来源：

NEW JOURNAL OF CHEMISTRY | 2016年 / 40卷 / 07期

关键词：

PHOTOINDUCED ELECTRON-TRANSFER; EFFICIENT PERIPHERAL FUNCTIONALIZATION; SENSITIZED SOLAR-CELLS; WATER-SOLUBILIZATION; PYRROLIC POSITION; ALPHA-DIONES; BUILDING-BLOCKS; BODIPY DYES; SYSTEMS; COORDINATION;

D O I：

10.1039/c5nj03247d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of functionalized porphyrins and their conjugates from meso-tetraarylporphyrins through the acylation and the oxidation of beta-aminoporphyrins was investigated. 2,3-Dioxochlorins were prepared by the oxidation of a variety of beta-aminoporphyrins and subsequently used in a condensation reaction with functionalized aromatic aldehydes and ammonium acetate to form beta-functionalized porphyrins bearing a fused imidazole ring. Under optimized experimental conditions both reactions tolerate various functional groups and afford the products in an appropriate overall yield. The mildness and usefulness of this methodology are illustrated by several examples including the synthesis of porphyrins bearing receptor groups and water-solubilizing moieties.

引用

页码：5758 / 5774

页数：17

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[1] ADSORPTIVE MECHANISM ON ACTIVATED CARBON IN THE LIQUID-PHASE .3. THE RELATIONSHIP BETWEEN THE PHYSICAL CONSTANTS OF ORGANIC-COMPOUNDS AND THEIR ADSORBABILITIES ON ACTIVATED CARBON FROM AN AQUEOUS-SOLUTION [J].