Per-o-methylated cyclodextrins for C60 solubilization and metal encapsulation

Abstract : Our previous work have developed DIBAL-H debenzylation of α-, β- and γ-CDBn, which generates regioselective functionalization on the primary rim. Moreover, DIBAL-H demethylation of α- and β-CDMe gives an access to regioselective modification on the secondary rim without changing the conformation of suger unit. Meanwhile, the optimized DIBAL-H demethylation could affordes the modification on the primary rim as well. Because of the large cavity of γ-CD on C60 solubilization and encapsulation, one of the goals of my work is to obtain the selectively modified γ-CDMe on the secondary rim. Based on DIBAL-H demethylation of α-, β- and γ-CDMe, 7 α-CD-C60 conjugates are under the biological evaluation as potential antiviral agents and a β-CD-C60 conjugate is being studied as a potential anti-allergic agent. Furthermore, 2A-γ-CDMe-C60 conjugate with secondary rim attachement displays the highest water-solubility among CD-C60 conjugates and γ-CD/C60 complexes. Both 2A-γ-CDMe-C60 conjugate and 6A-γ-CDMe-C60 conjugate with primary rim attachment showed higher 1O2 quantume yield than the reported CD-C60 conjugates under UV irradiation. In light of the methodology of DIBAL-H debenzylation, 6 water-soluble α- and β-CDMe-Ag(Cu, Au) complexes have been synthesized. X-ray crystal structures of α-CDMe-AgCl in both CDCl3 and water have been obtained. Besides, we got monomer α-CDMe-CuCCPh which is stable in water. In addition, α- and β-CDMe-AuCl have been as catalysts in regioselective, enantioselective cycloisomerization and lactonization in DCM and neat water.
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Xiaolei Zhu. Per-o-methylated cyclodextrins for C60 solubilization and metal encapsulation. Organic chemistry. Université Pierre et Marie Curie - Paris VI, 2017. English. ⟨NNT : 2017PA066624⟩. ⟨tel-02191531⟩

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