Synthesis, characterization, and supramolecular properties of a hydrophilic porphyrin-β-cyclodextrin conjugate

被引：33

作者：

Carofiglio, T

Fornasier, R

Lucchini, V

Simonato, L

Tonellato, U

机构：

[1] Univ Padua, Dipartimento Chim Inorgan Metallorgan & Anali, I-35100 Padua, Italy

[2] Univ Padua, Dipartimento Chim Organ, I-35100 Padua, Italy

[3] Univ Padua, CNR, Ctr Meccan Reaz Organ, I-35100 Padua, Italy

[4] Univ Venice, Dipartimento Sci Ambientali, I-30123 Venice, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 26期

关键词：

D O I：

10.1021/jo0010678

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reductive amination of 6-deoxy-6-formyl-beta -cyclodextrin with 5-(p-aminophenyl)-10,15,20-tris(p-sulfonatophenyl)porphyrin in the presence of an excess of sodium cyanoborohydride affords the hydrophilic cyclodextrin-porphyrin conjugate 3 in 23% yield. The structure of 3 was confirmed by NMR spectroscopy and mass spectrometry techniques. Compound 3 showed a marked tendency to dimerize in aqueous conditions via the formation of intermolecular porphyrin-cyclodextrin inclusion complexes and/or through electrostatic interactions. Information on the structure of these aggregates has been obtained by the use of circular dichroism and UV-vis spectroscopy. Aggregation can be avoided by the use of heptakis(2,3,6-tri-O-methyl)-beta -cyclodextrin (TM beta CD) that forms a 1:1 inclusion complex with compound 3.

引用

页码：9013 / 9021

页数：9

共 41 条

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