Reversible Control over Molecular Recognition in Surface-Bound Photoswitchable Hydrogen-Bonding Receptors: Towards Read–Write–Erase Molecular Printboards - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2013

Reversible Control over Molecular Recognition in Surface-Bound Photoswitchable Hydrogen-Bonding Receptors: Towards Read–Write–Erase Molecular Printboards

Résumé

The synthesis of an anthracene-bearing photoactive barbituric acid receptor and its subsequent grafting onto azide-terminated alkanethiol/Au self-assembled monolayers by using an CuI-catalyzed azide–alkyne reaction is reported. Monolayer characterization using contact-angle measurements, electrochemistry, and spectroscopic ellipsometry indicate that the monolayer conversion is fast and complete. Irradiation of the receptor leads to photodimerization of the anthracenes, which induces the open-to-closed gating of the receptor by blocking access to the binding site. The process is thermally reversible, and polarization-modulated IR reflection–absorption spectroscopy indicates that photochemical closure and thermal opening of the surface-bound receptors occur in 70 and 100 % conversion, respectively. Affinity of the open and closed surface-bound receptor was characterized by using force spectroscopy with a barbituric-acid-modified atomic force microscope tip.

Domaines

Chimie organique

Dates et versions

hal-01151718 , version 1 (13-05-2015)

Identifiants

Citer

Chih-Kai Liang, Galina V. Dubacheva, Thierry Buffeteau, Dominique Cavagnat, Philippe Hapiot, et al.. Reversible Control over Molecular Recognition in Surface-Bound Photoswitchable Hydrogen-Bonding Receptors: Towards Read–Write–Erase Molecular Printboards. Chemistry - A European Journal, 2013, CHEMPUBSOC EUROPE, 19 (38), pp.12748-12758. ⟨10.1002/chem.201301613⟩. ⟨hal-01151718⟩
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