Synthesis and characterization of a new photoinduced switchable ß-cyclodextrin dimer.
Beilstein J Org Chem
; 10: 2874-85, 2014.
Article
em En
| MEDLINE
| ID: mdl-25550753
ABSTRACT
This paper reports an efficient preparation of bridged bis-ß-CD AZO-CDim 1 bearing azobenzene as a linker and exhibiting high solubility in water. The photoisomerization properties were studied by UV-vis and HPLC and supported by ab initio calculations. The cis/trans ratio of AZO-CDim 1 is 793 without irradiation and 3763 after 120 min of irradiation at 365 nm; the reaction is reversible after irradiation at 254 nm. The photoinduced, switchable binding behavior of AZO-CDim 1 was evaluated by ITC, NMR and molecular modeling in the presence of a ditopic adamantyl guest. The results indicate that AZO-CDim 1 can form two different inclusion complexes with an adamantyl dimer depending on its photoinduced isomers. Both cavities of cis-AZO-CDim 1 are complexed simultaneously by two adamantyl units of the guest forming a 11 complex while trans-AZO-CDim 1 seems to lead to the formation of supramolecular polymers with an nn stoichiometry.
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MEDLINE
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En
Ano de publicação:
2014
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Article