Synthesis, characterization and chemisorption on gold of a β-cyclodextrin–lipoic acid conjugate

Carofiglio, Tommaso; Fornasier, Roberto; Jicsinszky, László; Tonellato, Umberto; Turco, Chiara

doi:10.1016/s0040-4039(01)01001-2

Cited by 15 publications

(11 citation statements)

References 10 publications

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“…3 Compounds such as 1,2-dithiolane-3-pentanoic acid (also known as thioctic acid, lipoic acid, or 1,2-dithiolane-3-valeric acid) have been used for various applications such as molecular switches, molecular machines, sensors, and protein immobilization. [4][5][6][7][8][9][10][11][12][13][14] A prominent example is the bistable Stoddart-Heath-type [2]rotaxane (1) anchored to gold electrodes, 4,15 which has already proved useful as a molecular switch. 15,16 The switch 1 is turned on and off reversibly upon the redoxinduced shuttling of the cyclobis-(paraquat-p-phenylene) (CB-PQT, blue) ring between two stations, tetrathiafulvalene (TTF, green) and 1,5-dioxynaphthalene (DNP, red).…”

Section: Introductionmentioning

confidence: 99%

Electron Transport through Cyclic Disulfide Molecular Junctions with Two Different Adsorption States at the Contact: A Density Functional Theory Study

Jang

Goddard

2008

J. Phys. Chem. C

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1,2-Dithiolane is a promising anchor group for attaching molecules to metal electrodes in molecular junction devices. This five-membered cyclic disulfide adsorbs on Au surfaces either in a cyclic fashion (with its disulfide bond intact, via molecular adsorption) or in an acyclic fashion (with its disulfide bond broken, via dissociative adsorption). Our density functional theory calculations show that the dissociative adsorption is slightly preferred, but both are stable. We also report nonequilibrium Green's function calculations showing that molecular junctions of cyclic and acyclic 1,2-dithiolanes sandwiched between two gold electrodes exhibit essentially the same insulating current-voltage characteristics at moderate bias voltages, despite the significant difference in their states of adsorption.

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Section: Introductionmentioning

confidence: 99%

Electron Transport through Cyclic Disulfide Molecular Junctions with Two Different Adsorption States at the Contact: A Density Functional Theory Study

Jang

Goddard

2008

J. Phys. Chem. C

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“…Cyclodextrins and modified cyclodextrins have been chemisorbed onto gold electrodes, − gold films, , gold-coated AFM cantilevers, and gold electrodes of a quartz microbalance to exploit the host−guest interactions of cyclodextrins with solution partners. Per-6-thio-β-CD and mono-6-lipoyl-amido-2,3,6- O -permethyl-β-CD have been added directly to gold nanoparticle solutions to form cyclodextrin-modified gold nanospheres. Recently, perthiolated cyclodextrins (CDs) have been used to modify gold nanospheres by their addition directly to the gold solution during its reduction. , In these studies, HAuCl 4 was reduced by sodium borohydride in the presence of perthiolated CDs in a solvent (either DMSO or dimethylformamide) milieu.…”

Section: Introductionmentioning

confidence: 99%

Control of the Size and Distribution of Gold Nanoparticles by Unmodified Cyclodextrins

et al. 2003

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We report and discuss how gold nanoparticles were synthesized by the reduction of hydrogen tetrachloroaurate(III) trihydrate by sodium citrate in the presence of unmodified α-cyclodextrin (CD), β-CD, and γ-CD. Gold nanoparticles were immobilized on poly(diallyldimethylammonium) chloride (PDDA) modified glass slides to enable AFM measurements. The particle size was dependent upon the type and concentration of cyclodextrin used as well as the sodium citrate concentration. An increase in the cyclodextrin concentration effected a shift of the particle size range from 12−15 to 4−6 nm with uniform particle size distribution. The homogeneity of the synthesized gold nanoparticles was also evident from transmission electron micrographs (TEMs). Synthesis of gold nanoparticles by the reduction of hydrogen tetrachloroaurate(III) trihydrate by sodium borohydride in the presence of cyclodextrins also reduced the particle size from 6−8 to 2−4 nm. The consecutive particle growth due to the mutual coalescence between nanoclusters and their neighboring free gold atoms was limited in the presence of CDs. FT-Raman, FT-IR spectroscopy, and mass spectrometry (MS) indicated that the synthesis procedure exhibited no effect on the cyclodextrins. There was no evidence that gold nanoparticles were included in the CD cavities.

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“…The anchoring groups are thiols, disulfides, or other S−S moieties breaking easily during chemisorption on gold, e.g., lipoic acid . The cyclic disulfide functionality of lipoic acid affords two binding sites on the gold surface per chemisorbed molecule, which was suggested to lead to more stable SAMs .…”

mentioning

confidence: 99%

“…8,9 The anchoring groups are thiols, disulfides, 10 or other S-S moieties breaking easily during chemisorption on gold, e.g., lipoic acid. 11 The cyclic disulfide functionality of lipoic acid affords two binding sites on the gold surface per chemisorbed molecule, which was suggested to lead to more stable SAMs. 12 Lipoyl derivatives of β-cyclodextrin with different length of the side chains were described first by He et al 13 Positional isomers of γ-CD derivatives with two lipoic ester groups per molecule were synthesized by Suzuki and co-workers.…”

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confidence: 99%

β-Cyclodextrin-Based Ferrocene-Imprinted Gold Electrodes

2003

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A new stepwise self-assembly procedure is described for the preparation of functional cyclodextrin-modified electrodes. The approach is based on the formation of alkanethiol/lipoylamide-beta-cyclodextrin monolayers with the thiol component responsible for blocking of the electrode surface and lipoylamide-beta-cyclodextrin molecules-for controlled opening of the access of the electroactive probe to the electrode. Functionalization of the electrode is achieved by means of a new cyclodextrin derivative-mono(6-deoxy-6-lipoylamide)-per-2,3,6-O-acetyl-beta-cyclodextrin-prepared in the peracetyl form and deacetylated directly on the electrode surface following the cyclodextrin self-assembly. The progress of deacetylation was monitored by the MALDI MS technique. Deacetylation caused opening of the active sites toward solution probes. The response toward ferrocene was found to be highly improved when ferrocene was added to the solution following self-assembly of cyclodextrin but prior to the thiol self-assembly step (imprinting method). The proposed synthesis and sequential monolayer formation scheme lead to well-organized and stable modified electrode surfaces with improved sensitivity toward solution species compared to other procedures of electrode modification with the cyclodextrin derivatives.

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Synthesis, characterization and chemisorption on gold of a β-cyclodextrin–lipoic acid conjugate

Cited by 15 publications

References 10 publications

Electron Transport through Cyclic Disulfide Molecular Junctions with Two Different Adsorption States at the Contact: A Density Functional Theory Study

Electron Transport through Cyclic Disulfide Molecular Junctions with Two Different Adsorption States at the Contact: A Density Functional Theory Study

Control of the Size and Distribution of Gold Nanoparticles by Unmodified Cyclodextrins

β-Cyclodextrin-Based Ferrocene-Imprinted Gold Electrodes

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