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
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
收藏
页码:9013 / 9021
页数:9
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