Synthesis, Characterization, and Supramolecular Properties of a Hydrophilic Porphyrin−β-Cyclodextrin Conjugate
- 30 November 2000
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (26) , 9013-9021
- https://doi.org/10.1021/jo0010678
Abstract
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.Keywords
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