3 years ago

Secondary-Rim γ-Cyclodextrin Functionalization to Conjugate with C60: Improved Efficacy as a Photosensitizer

Secondary-Rim γ-Cyclodextrin Functionalization to Conjugate with C60: Improved Efficacy as a Photosensitizer
Yongmin Zhang, René V. Bensasson, Xiaolei Zhu, Annamaria Quaranta, Matthieu Sollogoub
DIBAL-H-mediated demethylation provides a novel method to access secondary-rim functionalized γ-cyclodextrin. 2A,3B-Dihydroxyl-per-O-methylated-γ-cyclodextrin has been obtained, whose conjugation with C60 allows access to the most water-soluble C60 conjugate described so far. The water solubility of 0.12 m (550 mg mL−1) is 150 times higher than that of the native γ-CD/C60 complex. Its singlet oxygen (1O2) quantum yield is 0.39, an increase of one to two orders of magnitude compared to that of α(β)CD–C60 conjugates. DIBAL-H was used as molecular scalpel to provide an elegant entry to secondary-rim functionalized γ-CD, such as 2A,3B-dihydroxyl-per-O-methylated-γ-cyclodextrin. The conjugation of this diol with C60 allows access to the most water-soluble C60 conjugate described so far.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201700782

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