Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer
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 with...
| Main Authors: | , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.304 |
| _version_ | 1818360263326302208 |
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| author | Florian Hamon Claire Blaszkiewicz Marie Buchotte Estelle Banaszak-Léonard Hervé Bricout Sébastien Tilloy Eric Monflier Christine Cézard Laurent Bouteiller Christophe Len Florence Djedaini-Pilard |
| author_facet | Florian Hamon Claire Blaszkiewicz Marie Buchotte Estelle Banaszak-Léonard Hervé Bricout Sébastien Tilloy Eric Monflier Christine Cézard Laurent Bouteiller Christophe Len Florence Djedaini-Pilard |
| author_sort | Florian Hamon |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-13T20:58:01Z |
| format | Article |
| id | doaj.art-2ca89d3699d04486a878fa1f8b00abe4 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-13T20:58:01Z |
| publishDate | 2014-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-2ca89d3699d04486a878fa1f8b00abe42022-12-21T23:31:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-12-011012874288510.3762/bjoc.10.3041860-5397-10-304Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimerFlorian Hamon0Claire Blaszkiewicz1Marie Buchotte2Estelle Banaszak-Léonard3Hervé Bricout4Sébastien Tilloy5Eric Monflier6Christine Cézard7Laurent Bouteiller8Christophe Len9Florence Djedaini-Pilard10Université de Picardie Jules Verne, Laboratoire de Glycochimie – Antimicrobiens et Agroressources, LG2A FRE CNRS 3517, F-80039 Amiens, FranceUniversité de Picardie Jules Verne, Laboratoire de Glycochimie – Antimicrobiens et Agroressources, LG2A FRE CNRS 3517, F-80039 Amiens, FranceTransformations Intégrées de la Matière Renouvelable, TIMR EA4295 UTC/ESCOM, F-60200 Compiègne, FranceTransformations Intégrées de la Matière Renouvelable, TIMR EA4295 UTC/ESCOM, F-60200 Compiègne, FranceUniversité d’Artois, Unité de Catalyse et de Chimie du Solide (UCCS), CNRS, UMR 8181, Rue Jean Souvraz, SP 18, F-62307 Lens, FranceUniversité d’Artois, Unité de Catalyse et de Chimie du Solide (UCCS), CNRS, UMR 8181, Rue Jean Souvraz, SP 18, F-62307 Lens, FranceUniversité d’Artois, Unité de Catalyse et de Chimie du Solide (UCCS), CNRS, UMR 8181, Rue Jean Souvraz, SP 18, F-62307 Lens, FranceUniversité de Picardie Jules Verne, Laboratoire de Glycochimie – Antimicrobiens et Agroressources, LG2A FRE CNRS 3517, F-80039 Amiens, FranceSorbonne Universités, UPMC Université Paris 06, CNRS, UMR 8232, IPCM, Chimie des Polymères, F-75005, Paris, FranceTransformations Intégrées de la Matière Renouvelable, TIMR EA4295 UTC/ESCOM, F-60200 Compiègne, FranceUniversité de Picardie Jules Verne, Laboratoire de Glycochimie – Antimicrobiens et Agroressources, LG2A FRE CNRS 3517, F-80039 Amiens, FranceThis 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.https://doi.org/10.3762/bjoc.10.304azobenzenecyclodextrinsinclusion complexphotoisomerizationswitchable binding behavior |
| spellingShingle | Florian Hamon Claire Blaszkiewicz Marie Buchotte Estelle Banaszak-Léonard Hervé Bricout Sébastien Tilloy Eric Monflier Christine Cézard Laurent Bouteiller Christophe Len Florence Djedaini-Pilard Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer Beilstein Journal of Organic Chemistry azobenzene cyclodextrins inclusion complex photoisomerization switchable binding behavior |
| title | Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer |
| title_full | Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer |
| title_fullStr | Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer |
| title_full_unstemmed | Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer |
| title_short | Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer |
| title_sort | synthesis and characterization of a new photoinduced switchable β cyclodextrin dimer |
| topic | azobenzene cyclodextrins inclusion complex photoisomerization switchable binding behavior |
| url | https://doi.org/10.3762/bjoc.10.304 |
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