Beilstein Journal of Organic Chemistry p. 2874 - 2885 (2014)
Update date:2022-08-04
Topics:
Hamon, Florian
Blaszkiewicz, Claire
Buchotte, Marie
Banaszak-Lonard, Estelle
Bricout, Herv
Tilloy, Sbastien
Monflier, Eric
Czard, Christine
Bouteiller, Laurent
Len, Christophe
Djedaini-Pilard, Florence
This paper reports an efficient preparation of bridged bis--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 7:93 without irradiation and 37:63 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 1:1 complex while trans-AZO-CDim 1 seems to lead to the formation of supramolecular polymers with an n:n stoichiometry.
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