title: Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer.
abstract: This paper reports an efficient preparation of bridged bis-β-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.
authors.affiliation: Université de Picardie Jules Verne, Laboratoire de Glycochimie - Antimicrobiens et Agroressources, LG2A FRE CNRS 3517, F-80039 Amiens, France.
authors.forename: Florian
authors.initials: F
authors.lastname: Hamon
authors.affiliation: Université de Picardie Jules Verne, Laboratoire de Glycochimie - Antimicrobiens et Agroressources, LG2A FRE CNRS 3517, F-80039 Amiens, France ; Université d'Artois, Unité de Catalyse et de Chimie du Solide (UCCS), CNRS, UMR 8181, Rue Jean Souvraz, SP 18, F-62307 Lens, France.
authors.forename: Claire
authors.initials: C
authors.lastname: Blaszkiewicz
authors.affiliation: Transformations Intégrées de la Matière Renouvelable, TIMR EA4295 UTC/ESCOM, F-60200 Compiègne, France.
authors.forename: Marie
authors.initials: M
authors.lastname: Buchotte
authors.affiliation: Transformations Intégrées de la Matière Renouvelable, TIMR EA4295 UTC/ESCOM, F-60200 Compiègne, France.
authors.forename: Estelle
authors.initials: E
authors.lastname: Banaszak-Léonard
authors.affiliation: Université d'Artois, Unité de Catalyse et de Chimie du Solide (UCCS), CNRS, UMR 8181, Rue Jean Souvraz, SP 18, F-62307 Lens, France.
authors.forename: Hervé
authors.initials: H
authors.lastname: Bricout
authors.affiliation: Université d'Artois, Unité de Catalyse et de Chimie du Solide (UCCS), CNRS, UMR 8181, Rue Jean Souvraz, SP 18, F-62307 Lens, France.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Tilloy
authors.affiliation: Université d'Artois, Unité de Catalyse et de Chimie du Solide (UCCS), CNRS, UMR 8181, Rue Jean Souvraz, SP 18, F-62307 Lens, France.
authors.forename: Eric
authors.initials: E
authors.lastname: Monflier
authors.affiliation: Université de Picardie Jules Verne, Laboratoire de Glycochimie - Antimicrobiens et Agroressources, LG2A FRE CNRS 3517, F-80039 Amiens, France.
authors.forename: Christine
authors.initials: C
authors.lastname: Cézard
authors.affiliation: Sorbonne Universités, UPMC Université Paris 06, CNRS, UMR 8232, IPCM, Chimie des Polymères, F-75005, Paris, France ; CNRS, UMR 8232, IPCM, Chimie des Polymères, F-75005, Paris, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Bouteiller
authors.affiliation: Transformations Intégrées de la Matière Renouvelable, TIMR EA4295 UTC/ESCOM, F-60200 Compiègne, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Len
authors.affiliation: Université de Picardie Jules Verne, Laboratoire de Glycochimie - Antimicrobiens et Agroressources, LG2A FRE CNRS 3517, F-80039 Amiens, France.
authors.forename: Florence
authors.initials: F
authors.lastname: Djedaini-Pilard
keywords: azobenzene; cyclodextrins; inclusion complex; photoisomerization; switchable binding behavior