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Improving the Switching Capacity of Glyco‐Self‐Assembled Monolayers on Au(111)

Self‐assembled monolayers (SAMs) decorated with photoisomerizable azobenzene glycosides are useful tools for investigating the effect of ligand orientation on carbohydrate recognition. However, photoswitching of SAMs between two specific states is characterized by a limited capacity. The goal of thi...

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Autores principales: Fast, Ellen, Schlimm, Alexander, Lautenschläger, Irene, Clausen, Kai Uwe, Strunskus, Thomas, Spormann, Carina, Lindhorst, Thisbe K., Tuczek, Felix
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6973251/
https://www.ncbi.nlm.nih.gov/pubmed/31660639
http://dx.doi.org/10.1002/chem.201903644
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author Fast, Ellen
Schlimm, Alexander
Lautenschläger, Irene
Clausen, Kai Uwe
Strunskus, Thomas
Spormann, Carina
Lindhorst, Thisbe K.
Tuczek, Felix
author_facet Fast, Ellen
Schlimm, Alexander
Lautenschläger, Irene
Clausen, Kai Uwe
Strunskus, Thomas
Spormann, Carina
Lindhorst, Thisbe K.
Tuczek, Felix
author_sort Fast, Ellen
collection PubMed
description Self‐assembled monolayers (SAMs) decorated with photoisomerizable azobenzene glycosides are useful tools for investigating the effect of ligand orientation on carbohydrate recognition. However, photoswitching of SAMs between two specific states is characterized by a limited capacity. The goal of this study is the improvement of photoswitchable azobenzene glyco‐SAMs. Different concepts, in particular self‐dilution and rigid biaryl backbones, have been investigated. The required SH‐functionalized azobenzene glycoconjugates were synthesized through a modular approach, and the respective glyco‐SAMs were fabricated on Au(111). Their photoswitching properties have been extensively investigated by applying a powerful set of methods (IRRAS, XPS, and NEXAFS). Indeed, the combination of tailor‐made biaryl‐azobenzene glycosides and suitable diluent molecules led to photoswitchable glyco‐SAMs with a significantly enhanced and unprecedented switching capacity.
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spelling pubmed-69732512020-01-27 Improving the Switching Capacity of Glyco‐Self‐Assembled Monolayers on Au(111) Fast, Ellen Schlimm, Alexander Lautenschläger, Irene Clausen, Kai Uwe Strunskus, Thomas Spormann, Carina Lindhorst, Thisbe K. Tuczek, Felix Chemistry Full Papers Self‐assembled monolayers (SAMs) decorated with photoisomerizable azobenzene glycosides are useful tools for investigating the effect of ligand orientation on carbohydrate recognition. However, photoswitching of SAMs between two specific states is characterized by a limited capacity. The goal of this study is the improvement of photoswitchable azobenzene glyco‐SAMs. Different concepts, in particular self‐dilution and rigid biaryl backbones, have been investigated. The required SH‐functionalized azobenzene glycoconjugates were synthesized through a modular approach, and the respective glyco‐SAMs were fabricated on Au(111). Their photoswitching properties have been extensively investigated by applying a powerful set of methods (IRRAS, XPS, and NEXAFS). Indeed, the combination of tailor‐made biaryl‐azobenzene glycosides and suitable diluent molecules led to photoswitchable glyco‐SAMs with a significantly enhanced and unprecedented switching capacity. John Wiley and Sons Inc. 2019-12-10 2020-01-07 /pmc/articles/PMC6973251/ /pubmed/31660639 http://dx.doi.org/10.1002/chem.201903644 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Fast, Ellen
Schlimm, Alexander
Lautenschläger, Irene
Clausen, Kai Uwe
Strunskus, Thomas
Spormann, Carina
Lindhorst, Thisbe K.
Tuczek, Felix
Improving the Switching Capacity of Glyco‐Self‐Assembled Monolayers on Au(111)
title Improving the Switching Capacity of Glyco‐Self‐Assembled Monolayers on Au(111)
title_full Improving the Switching Capacity of Glyco‐Self‐Assembled Monolayers on Au(111)
title_fullStr Improving the Switching Capacity of Glyco‐Self‐Assembled Monolayers on Au(111)
title_full_unstemmed Improving the Switching Capacity of Glyco‐Self‐Assembled Monolayers on Au(111)
title_short Improving the Switching Capacity of Glyco‐Self‐Assembled Monolayers on Au(111)
title_sort improving the switching capacity of glyco‐self‐assembled monolayers on au(111)
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6973251/
https://www.ncbi.nlm.nih.gov/pubmed/31660639
http://dx.doi.org/10.1002/chem.201903644
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