Reversible Control of Nanoparticle Functionalization and Physicochemical Properties by Dynamic Covalent Exchange

Existing methods for the covalent functionalization of nanoparticles rely on kinetically controlled reactions, and largely lack the sophistication of the preeminent oligonucleotide‐based noncovalent strategies. Here we report the application of dynamic covalent chemistry for the reversible modificat...

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Published inAngewandte Chemie (International ed.) Vol. 54; no. 14; pp. 4187 - 4191
Main Authors della Sala, Flavio, Kay, Euan R.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 27.03.2015
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Communications
Covalence
dynamic covalent chemistry
Dynamic mechanical properties
Dynamics
Exchange
gold nanoparticles
Hydrazones
Hydrazones - chemistry
Magnetic Resonance Spectroscopy
Monolayers
Nanoparticles
Nanostructure
Real time
supramolecular chemistry
Surface Properties
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Summary:Existing methods for the covalent functionalization of nanoparticles rely on kinetically controlled reactions, and largely lack the sophistication of the preeminent oligonucleotide‐based noncovalent strategies. Here we report the application of dynamic covalent chemistry for the reversible modification of nanoparticle (NP) surface functionality, combining the benefits of non‐biomolecular covalent chemistry with the favorable features of equilibrium processes. A homogeneous monolayer of nanoparticle‐bound hydrazones can undergo quantitative dynamic covalent exchange. The pseudomolecular nature of the NP system allows for the in situ characterization of surface‐bound species, and real‐time tracking of the exchange reactions. Furthermore, dynamic covalent exchange offers a simple approach for reversibly switching—and subtly tuning—NP properties such as solvophilicity. Ligand swap shop: Dynamic covalent hydrazone exchange within a homogeneous monolayer bound to the surface of gold nanoparticles is tracked in real time. The introduction of appropriately functionalized aldehyde exchange units allows reversible tuning of nanoparticle solvophilicity and presents a generalizable covalent approach to postsynthetic modification of nanoparticle functionalization and properties.
Bibliography:Funded Access
ark:/67375/WNG-4GMZWV5N-Z
Royal Society of Edinburgh/Scottish Government Fellowship
istex:C81D8DAB88B5D5C96FB098950AD05E0EB8A6DC98
EPSRC - No. EP/K016342/1
University of St Andrews
This work was supported by the EPSRC (EP/K016342/1 and DTG), the University of St Andrews, and by a Royal Society of Edinburgh/Scottish Government Fellowship (E.R.K.). We are grateful to Dr. Catherine Botting and the University of St Andrews BSRC Mass Spectrometry and Proteomics Facility (supported by the Wellcome Trust) for on-NP LDI-MS measurements, Dr. Tomas Lebl and Melanja Smith for assistance with NMR measurements, Ross Blackley for assistance with TEM measurements, and the EPSRC UK National Mass Spectrometry Facility (NMSF) at Swansea University.
Wellcome Trust
ArticleID:ANIE201409602
This work was supported by the EPSRC (EP/K016342/1 and DTG), the University of St Andrews, and by a Royal Society of Edinburgh/Scottish Government Fellowship (E.R.K.). We are grateful to Dr. Catherine Botting and the University of St Andrews BSRC Mass Spectrometry and Proteomics Facility (supported by the Wellcome Trust) for on‐NP LDI‐MS measurements, Dr. Tomas Lebl and Melanja Smith for assistance with NMR measurements, Ross Blackley for assistance with TEM measurements, and the EPSRC UK National Mass Spectrometry Facility (NMSF) at Swansea University.
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201409602