David N Reinhoudt

Publications (369)1668.16 Total impact

• Article: Nonlinear Amplification of a Supramolecular Complex at a Multivalent Interface.

  Shu-Han Hsu, M Deniz Yilmaz, David N Reinhoudt, Aldrik H Velders, Jurriaan Huskens
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  ABSTRACT: Competition with a monovalent cyclodextrin host (blue cones) in solution drives the multivalent binding of a Eu(3+) complex and a sensitizer molecule to cyclodextrin monolayers through a nonlinear self-assembly process. Adamantyl groups (light-blue spheres) are attached to the EDTA ligand (black) and the antenna molecule (orange), which has a carboxylate group for coordination to the Eu(3+) ion (yellow or red in free or complexed form, respectively).
  Angewandte Chemie International Edition 11/2012; · 13.45 Impact Factor
• Source

  Available from: Mercedes Crego-Calama

  Article: Exploring the transferability of large supramolecular assemblies to the vacuum-solid interface

  Wei Xu, Mingdong Dong, Henkjan Gersen, Socorro Vázquez-Campos, Xavier Bouju, Erik Lægsgaard, Ivan Stensgaard, Mercedes Crego-Calama, David N. Reinhoudt, Trolle R. Linderoth, Flemming Besenbacher
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  ABSTRACT: We present an interplay of high-resolution scanning tunneling microscopy imaging and the corresponding theoretical calculations based on elastic scattering quantum chemistry techniques of the adsorption of a gold-functionalized rosette assembly and its building blocks on a Au(111) surface with the goal of exploring how to fabricate functional 3-D molecular nanostructures on surfaces. The supramolecular rosette assembly stabilized by multiple hydrogen bonds has been sublimed onto the Au(111) surface under ultra-high vacuum conditions; the resulting surface nanostructures are distinctly different from those formed by the individual molecular building blocks of the rosette assembly, suggesting that the assembly itself can be transferred intact to the surface by in situ thermal sublimation. This unanticipated result will open up new perspectives for growth of complex 3-D supramolecular nanostructures at the vacuum-solid interface. KeywordsSelf-assembly-surface nanostructures-scanning tunneling microscopy-supramolecular assembly-hydrogen bonding
  Nano Research 04/2012; 2(7):535-542. · 6.97 Impact Factor
• Article: Electron-Induced Dynamics of Heptathioether β-Cyclodextrin Molecules.

  Avijit Kumar, René Heimbuch, Kim S Wimbush, Hasan Ateşçi, Adil Acun, David N Reinhoudt, Aldrik H Velders, Harold J W Zandvliet
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  ABSTRACT: Variable-temperature scanning tunneling microscopy (STM) and spectroscopy (STS) measurements are performed on heptathioether β-cyclodextrin (β-CD) self-assembled monolayers (SAMs) on Au. The β-CD molecules exhibit very rich dynamical behavior, which is not apparent in ensemble-averaged studies. The dynamics are reflected in the tunneling current-time traces, which are recorded with the STM feedback loop disabled. The dynamics are temperature independent, but increase with increasing tunneling current and sample bias, thus indicating that the conformational changes of the β-CD molecules are induced by electrons that tunnel inelastically. Even for sample biases as low as 10 mV, well-defined levels are observed in the tunneling current-time traces. These jumps are attributed to the excitations of the molecular vibration of the macrocyclic β-CD molecule. The results are of great importance for a proper understanding of transport measurements in SAMs.
  Small 11/2011; · 8.35 Impact Factor
• Article: Electrochemical stability of self-assembled alkylphosphate monolayers on conducting metal oxides.

  Oktay Yildirim, M Deniz Yilmaz, David N Reinhoudt, Dave H A Blank, Guus Rijnders, Jurriaan Huskens
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  ABSTRACT: Alkylphosphate self-assembled monolayers (SAMs) were prepared on Nb-doped SrTiO(3) (Nb-STO) conducting metal oxide substrates. Unlike thiols on gold, the alkylphosphate SAMs on Nb-STO exhibited an electrochemical stability over a wide voltage range from -2 to 2 V. Cyclic voltammetry showed that the SAM modification inhibited the electrochemical activity of the underlying conducting substrate with an efficiency dependent on the chain length. Impedance spectroscopy showed that SAM-modified Nb-STO substrates have a significantly higher resistance than bare substrates.
  Langmuir 08/2011; 27(16):9890-4. · 4.19 Impact Factor
• Article: Gradient-driven motion of multivalent ligand molecules along a surface functionalized with multiple receptors.

  András Perl, Alberto Gomez-Casado, Damien Thompson, Henk H Dam, Pascal Jonkheijm, David N Reinhoudt, Jurriaan Huskens
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  ABSTRACT: The kinetics of multivalent (multisite) interactions at interfaces is poorly understood, despite its fundamental importance for molecular or biomolecular motion and molecular recognition events at biological interfaces. Here, we use fluorescence microscopy to monitor the spreading of mono-, di- and trivalent ligand molecules on a receptor-functionalized surface, and perform multiscale computer simulations to understand the surface diffusion mechanisms. Analogous to chemotaxis, we found that the spreading is directional (along a developing gradient of vacant receptor sites) and is strongly dependent on ligand valency and concentration of a competing monovalent receptor in solution. We identify multiple surface diffusion mechanisms, which we call walking, hopping and flying. The study shows that the interfacial behaviour of multivalent systems is much more complex than that of monovalent ones.
  Nature Chemistry 04/2011; 3(4):317-22. · 20.52 Impact Factor
• Article: Nanosize metallodendrimers

  Frank C. J. M. van Veggel, Wilhelm T. S. Huck, David N. Reinhoudt
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  ABSTRACT: Building blocks have been designed for the non-covalent formation of nanosize assemblies. As non-covalent interactions coordination chemistry and hydrogen bonding have been used. The self-assembly process leads to spherical assemblies with diameters in the range of 100 to 400 nm, with standard deviations in the order of 10–15%. The controlled assembly approach allows a precise controll of size and assemblies with molecular weights up to 10,000 Dalton have been realized. Finally, we have developed a strategy in which hydrogen bonding and coordination chemistry can be applied “orthogonally”
  Macromolecular Symposia 03/2011; 131(1):165 - 173.
• Article: Strategies for patterning biomolecules with dip-pen nanolithography.

  Chien-Ching Wu, David N Reinhoudt, Cees Otto, Vinod Subramaniam, Aldrik H Velders
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  ABSTRACT: Dip-pen nanolithography (DPN) is an atomic force microscopy (AFM)-based lithography technique, which has the ability to fabricate patterns with a feature size down to approximately 15 nm using both top-down and bottom-up approaches. DPN utilizes the water meniscus formed between an AFM tip and a substrate to transfer ink molecules onto surfaces. A major application of this technique is the fabrication of micro- and nano-arrays of patterned biomolecules. To achieve this goal, a variety of chemical approaches has been used. This review concisely describes the development of DPN in the past decade and presents the related chemical strategies that have been reported to fabricate biomolecular patterns with DPN at micrometer and nanometer scale, classified into direct- and indirect DPN methodologies, discussing tip-functionalization strategies as well.
  Small 03/2011; 7(8):989-1002. · 8.35 Impact Factor
• Chapter: Biomedical Applications of Metal‐Containing Luminophores

  Albert Ruggi, David N. Reinhoudt, Aldrik H. Velders
  02/2011: pages 383 - 406; , ISBN: 9783527633104
• Article: Patterning of peptide nucleic acids using reactive microcontact printing.

  Alessandro Calabretta, Dorothee Wasserberg, Geertruida A Posthuma-Trumpie, Vinod Subramaniam, Aart van Amerongen, Roberto Corradini, Tullia Tedeschi, Stefano Sforza, David N Reinhoudt, Rosangela Marchelli, Jurriaan Huskens, Pascal Jonkheijm
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  ABSTRACT: PNAs (peptide nucleic acids) have been immobilized onto surfaces in a fast, accurate way by employing reactive microcontact printing. Surfaces have been first modified with aldehyde groups to react with the amino end of the synthesized PNAs. When patterning fluorescein-labeled PNAs by reactive microcontact printing using oxygen-oxidized polydimethylsiloxane stamps, homogeneous arrays were fabricated and characterized using optical methods. PNA-patterned surfaces were hybridized with complementary and mismatched dye-labeled oligonucleotides to test their ability to recognize DNA sequences. The stability and selectivity of the PNA-DNA duplexes on surfaces have been verified by fluorescence microscopy, and the melting curves have been recorded. Finally, the technique has been applied to the fabrication of chips by spotting a PNA microarray onto a flat PDMS stamp and reproducing the same features onto many slides. The chips were finally applied to single nucleotide polymorphism detection on oligonucleotides.
  Langmuir 02/2011; 27(4):1536-42. · 4.19 Impact Factor
• Article: Magnetic nanoparticle assembly on surfaces using click chemistry.

  Sachin Kinge, Tian Gang, Wouter J M Naber, Wilfred G van der Wiel, David N Reinhoudt
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  ABSTRACT: Controlled assembly of ferromagnetic nanoparticles on surfaces is of crucial importance for a range of spintronic and data storage applications. Here, we present a novel method for assembling monolayers of ferromagnetic FePt nanoparticles on silicon oxide substrates using "click chemistry". Reaction of alkyne-functionalized FePt nanoparticles with azide-terminated self-assembled monolayers (SAMs), on silicon oxide, leads to the irreversible attachment of magnetic nanoparticles to the surface via triazole linkers. Based on this covalent interaction, well-packed monolayers of FePt nanoparticles were prepared and nanoparticle patterns are generated on surfaces via microcontact printing (μCP).
  Langmuir 01/2011; 27(2):570-4. · 4.19 Impact Factor
• Article: Dendritic ruthenium(II)-based dyes tuneable for diagnostic or therapeutic applications.

  Albert Ruggi, Chantal Beekman, Dorothee Wasserberg, Vinod Subramaniam, David N Reinhoudt, Fijs W B van Leeuwen, Aldrik H Velders
  Chemistry 01/2011; 17(2):464-7. · 5.93 Impact Factor
• Article: Control over rectification in supramolecular tunneling junctions.

  Kim S Wimbush, William F Reus, Wilfred G van der Wiel, David N Reinhoudt, George M Whitesides, Christian A Nijhuis, Aldrik H Velders
  Angewandte Chemie International Edition 12/2010; 49(52):10176-80. · 13.45 Impact Factor
• Article: A brush-gel/metal-nanoparticle hybrid film as an efficient supported catalyst in glass microreactors.

  Francesca Costantini, Edmondo M Benetti, Roald M Tiggelaar, Han J G E Gardeniers, David N Reinhoudt, Jurriaan Huskens, G Julius Vancso, Willem Verboom
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  ABSTRACT: A polymer-brush-based material was applied for the formation and in situ immobilization of silver and palladium nanoparticles, as a catalytic coating on the inner wall of glass microreactors. The brush film was grown directly on the microchannel interior by means of atom-transfer radical polymerization (ATRP), which allows control over the polymer film thickness and therefore permits the tuning of the number of nanoparticles formed on the channel walls. The wide applicability of the catalytic devices is demonstrated for the reduction of 4-nitrophenol and for the Heck reaction.
  Chemistry 11/2010; 16(41):12406-11. · 5.93 Impact Factor
• Article: Visualizing resonance energy transfer in supramolecular surface patterns of β-CD-functionalized quantum dot hosts and organic dye guests by fluorescence lifetime imaging.

  Denis Dorokhin, Shu-Han Hsu, Nikodem Tomczak, Christian Blum, Vinod Subramaniam, Jurriaan Huskens, David N Reinhoudt, Aldrik H Velders, G Julius Vancso
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  ABSTRACT: Detection of an analyte via supramolecular host-guest binding and quantum dot (QD)-based fluorescence resonance energy transfer (FRET) signal transduction mechanism is demonstrated. Surface patterns consisting of CdSe/ZnS QDs functionalized at their periphery with β-cyclodextrin (β-CD) were obtained by immobilization of the QDs from solution onto glass substrates patterned with adamantyl-terminated poly(propylene imine) dendrimeric "glue." Subsequent formation of host-guest complexes between vacant β-CD on the QD surface and an adamantyl-functionalized lissamine rhodamine resulting in FRET was confirmed by fluorescence microscopy, spectroscopy, and fluorescence lifetime imaging microscopy (FLIM).
  Small 11/2010; 6(24):2870-6. · 8.35 Impact Factor
• Article: Metal nanoparticle wires formed by an integrated nanomolding-chemical assembly process: fabrication and properties.

  Xuexin Duan, Myoung-Hwan Park, Yiping Zhao, Erwin Berenschot, Zheyao Wang, David N Reinhoudt, Vincent M Rotello, Jurriaan Huskens
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  ABSTRACT: We report here the use of nanomolding in capillaries (NAMIC) coupled with dithiocarbamate (DTC) chemistry to fabricate sub-50 nm quasi-1D arrays of 3.5 nm core gold nanoparticles (Au NPs) over large areas. Owing to chemical immobilization via the DTC bond, the patterned NP systems are stable in water and organic solvents, thus allowing the surface modification of the patterned Au NP arrays through thiol chemistry and further orthogonal binding of proteins. The electrical properties of these patterned Au NP wires have also been studied. Our results show that NAMIC combined with surface chemistry is a simple but powerful tool to create metal NP arrays that can potentially be applied to fabricate nanoelectronic or biosensing devices.
  ACS Nano 11/2010; 4(12):7660-6. · 10.77 Impact Factor
• Article: Enzyme-functionalized polymer brush films on the inner wall of silicon-glass microreactors with tunable biocatalytic activity.

  Francesca Costantini, Edmondo M Benetti, David N Reinhoudt, Jurriaan Huskens, G Julius Vancso, Willem Verboom
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  ABSTRACT: The lipase from Candida Rugosa was immobilized to a poly(methacrylic acid) polymer brush layer, grown on the inner wall of silicon-glass microreactors. The hydrolysis of 4-nitrophenyl acetate was used as a model reaction to study the activity of this biocatalytic system. The amount of bound lipase could be tuned by changing the polymerization time of the brush formation. The Michaelis-Menten constants and V(max) values, determined for immobilized and free lipase, are similar, demonstrating that the lipase's substrate affinity and its activity remain unchanged upon immobilization to the microchannel wall.
  Lab on a Chip 10/2010; 10(24):3407-12. · 5.67 Impact Factor
• Article: An iridium(III)-caged complex with low oxygen quenching.

  Albert Ruggi, Miguel Berenguel Alonso, David N Reinhoudt, Aldrik H Velders
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  ABSTRACT: We here report the synthesis and structural characterization of the first iridium(III) complex with a caged ligand structure, which shows a 80% decrease of oxygen quenching compared to the archetypical Ir(ppy)(3).
  Chemical Communications 09/2010; 46(36):6726-8. · 6.17 Impact Factor
• Article: Inversion of enantioselectivity of serine proteases

  Jaap Broos, Johan F. J. Engbersen, Willem Verboom, David N. Reinhoudt
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  ABSTRACT: The enantioselectivity of serine proteases in the transesterification of N-acetyl-(D,L)- phenylalanine esters with propan-1-ol in cyclohexane is strongly influenced by the leaving ability of the alcoholate group. Moreover the enantioselectivity is greatly influenced by the addition of small amounts (0.33 M) of organic additives. Addenda with a small molecular volume like e.g. ethanol and acetonitrile increase the rate for the L-enantiomer whereas alcohols with bulky alkyl groups like e.g. tert-butanol and 2-methylbutan-2-ol enhance the activity of the enzyme towards the D-enantiomer. This enables a rational tuning of the enantioselectivity as was demonstrated for four different proteases (-chymotrypsin, subtilisin Carlsberg, Aspergillus oryzae protease, and elastase).
  Recueil des Travaux Chimiques des Pays-Bas. 09/2010; 114(4‐5):255 - 257.
• Article: Stereoselective synthesis of cis and trans four‐membered cyclic nitrones

  Peter J. S. S. van Eijk, Cor Overkempe, Willem P. Trompenaars, David N. Reinhoudt, Lauri M. Manninen, Gerrit J. van Hummel, Sybolt Harkema
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  ABSTRACT: Nitroalkenes 3–5 react with ynamines (1-aminoacetylenes) 6 to yield four-membered cyclic nitrones (2,3-dihydroazete 1-oxides) 7–13. The nitroalkenes 3 and 5c give the cis fourmembered cyclic nitrones 7–11, whereas 4 and 5b yield the trans four-membered cyclic nitrones 12–13 upon reaction with 6. Nitroalkene 4i reacts with 6c to give a 1:1 mixture of the cis and trans four-membered cyclic nitrones 9g and 13i. The trans stereochemistry of trans-N,N-diethyl-2, 3-dihydro-3-(2-methoxynaphthalenyl)-2-methyl-4-phenyl-2-azetecarboxamide 1-oxide (13k) was elucidated by means of X-ray analysis. Only from the reaction of 1-nitrocyclopentene (5a) with 6c, the initially formed (4 + 2) cycloadduct, the nitronic ester 17 has been isolated. The thermal ring contraction of 17 yields 3a, 4, 5, 6-tetrahydro-N,N-dimethyl-3-phenyl-3H-cyclopent[c]isoxazole-3- carboxamide (19), the structure of which was established by X-ray analysis. The trans four-membered cyclic nitrones are thermally relatively stable compared with the cis nitrones. The mechanism of the stereoselective formation of the nitrones is related to the conformation of the (4 + 2) cycloadduct 16, which could be correlated with Chem-X and MNDO calculations.
  Recueil des Travaux Chimiques des Pays-Bas. 09/2010; 107(2):27 - 39.
• Article: Reaction of four‐membered cyclic nitrones with acetyl chlorideα. X‐Ray crystal structures of 2‐[(acetyloxy)amino]‐N,N‐diethyl‐2‐methyl‐4‐oxo‐3‐phenylpentanamide and 1‐acetyl‐3‐chloro‐N, N‐diethyl‐2‐methyl‐4‐methylene‐3‐phenyl‐2‐azetidinecarboxamide

  Peter J. S. S. van Eijk, Willem P. Trompenaars, David N. Reinhoudt, Sybolt Harkema
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  ABSTRACT: Reactions of the four-membered cyclic nitrones 1 with acetyl chloride differ strongly from those of other (cyclic) nitrones. In the presence of water, the nitrones 1 yield the 2-[(acetyloxy)-amino]-N,N-diethylalkanamides 4. The structure of 4b was confirmed by X-ray analysis. In the absence of water, the N,N-diethyl-4-methylene-2-azetidinecarboxamides 5 or the N,N-diethyl-2,3-dihydro-2-azetecarboxamides 6 were obtained. X-ray analysis elucidated the structure of 5a. Under acidic conditions, compounds 5a yielded the 2-oxa-5-azabicyclo[2.1.1]hexan-3-one derivative 13. Acid hydrolysis of 6a gave the -chloroketone derivative 18 and the 2-oxopropanamide derivative 19.
  Recueil des Travaux Chimiques des Pays-Bas. 09/2010; 107(2):52 - 62.