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Secondary‐Rim γ‐Cyclodextrin Functionalization to Conjugate with C 60 : Improved Efficacy as a Photosensitizer
Author(s) -
Zhu Xiaolei,
Quaranta Annamaria,
Bensasson René V.,
Sollogoub Matthieu,
Zhang Yongmin
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700782
Subject(s) - singlet oxygen , cyclodextrin , conjugate , photosensitizer , chemistry , demethylation , quantum yield , photochemistry , surface modification , yield (engineering) , solubility , combinatorial chemistry , oxygen , materials science , organic chemistry , fluorescence , mathematics , biochemistry , mathematical analysis , gene expression , physics , quantum mechanics , metallurgy , dna methylation , gene
DIBAL‐H‐mediated demethylation provides a novel method to access secondary‐rim functionalized γ‐cyclodextrin. 2 A ,3 B ‐Dihydroxyl‐per‐ O ‐methylated‐γ‐cyclodextrin has been obtained, whose conjugation with C 60 allows access to the most water‐soluble C 60 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/C 60 complex. Its singlet oxygen ( 1 O 2 ) quantum yield is 0.39, an increase of one to two orders of magnitude compared to that of α(β)CD–C 60 conjugates.