Ambiphile Tripod‐Komplexe: Synthese und Komplexchemie langkettiger funktionalisierter Tripod‐Liganden RC(CH2PPh2)3 mit R = Pentyl oder 8‐Nonenyl

Muth, A.; Asam, A.; Hüttner, Gottfried; Barth, Annette; Zsolnai, László

doi:10.1002/cber.19941270205

Cited by 21 publications

(8 citation statements)

References 24 publications

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“…[Fe 4 (Y) 2 (tmhd) 6 ] ( 1 ) (H 3 Y = 2-(4-chloro-phenyl)-2-hydroxymethyl-propane-1,3-diol) was prepared as described elsewhere . Ac 3 Z was obtained from H 3 Z following a literature procedure…”

Section: Methodsmentioning

confidence: 99%

XPS, FTIR-ATR, and AFM Structural Study of Silicon-Grafted Triol Monolayers for Controlled Anchoring of Single Molecule Magnets

et al. 2010

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The structures of monolayers on Si(100) made up of two acetyl-protected triol ligands, derived from 2-hydroxymethyl-propane-1,3-diol, namely, R-C(CH2OAc)3 with R = CH2CH−(CH2)9−O−CH2− and R = CH2CH−(CH2)7−, have been investigated. After deprotection, the two ligands are well-suited receptors for anchoring molecular functionalities, such as Fe4 single molecule magnets, to the Si surface through OH groups. Monolayers were obtained by the hydrosilylation reactions between H-terminated Si(100) and the CH2CH− end groups and were prepared in pure form or diluted with inert 1-alkenes to achieve an accurate control over the concentration and concerted orientation of the receptors on the surface. Subsequent anchoring of a Fe4 cluster, especially designed for a vertical atom sequence, has been expedient to clarify the influence of ligand mole fraction on the ordering of molecular receptors. We have achieved insight into the related structures and morphologies by combining angle-resolved X-ray photoelectron spectroscopy (AR-XPS), FTIR-attenuated total reflection (ATR) spectroscopy, and atomic force microscopy (AFM), including force lithography experiments. There is evidence that steric hindrances of apical groups are crucial for surface concentrations and, in turn, for geometrical orientation of the tethering units. Aging effects on monolayer structures and possible recovery processes have also been evaluated.

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Section: Methodsmentioning

confidence: 99%

XPS, FTIR-ATR, and AFM Structural Study of Silicon-Grafted Triol Monolayers for Controlled Anchoring of Single Molecule Magnets

et al. 2010

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“…1,1,1-Tris(hydroxymethyl)undecan (1a) and 1,1,1-tris(hydroxymethyl)dec-9-en (1b) were prepared by methods reported elsewhere. 3,5 Triphenylphosphane (23.6 g, 90 mmol) was dissolved in 300 mL THF. The solution was cooled to 0°C and 18.2 g (90 mmol, 17.6 mL) diisopropylazodicarboxylate (DIAD) were added slowly and under thorough stirring.…”

Section: Preparation Of Thiols 4a and 4bmentioning

confidence: 99%

“…4 The halogenation of the long-chain alcohol under different conditions is either not complete or causes decomposition as already found by Huttner in the case of 1b. 5 Treating the triol 1a with PBr 3 6,7 or with a mixture of P(OPh) 3 and PhBr in a modified Michaelis-Arbuzov reaction 8 did not produce the bromide but the bicyclic phosphite 2. By the simple addition of PBr 3 to 1 in diethylether the phosphite 2 can be synthesized in good yields and purity.…”

mentioning

confidence: 99%

Amphiphilic Trithiols RC(CH₂SH)₃

Wojczykowski¹,

Jutzi²

2006

Synlett

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We report on the synthesis of the amphiphilic molecules 1,1,1-tris(mercaptomethyl)undecane and 1,1,1-tris(mercaptomethyl)dec-9-ene starting from the corresponding tris(hydroxymethyl) compounds. In addition we describe the synthesis of an amphiphilic phosphite ligand possessing only one alkyl chain. These compounds are potential substrates for the monolayer protection of 2D surfaces and nanoparticles.The enormous interest in solution-phase synthesized nanoparticles is a challenge not only for physicists and material scientists but also for chemists working in the field of molecular synthesis. A way to improve and adjust properties of such nanoparticles is the use of well-designed ligands. One major application for nanoparticles is the labeling of functionalized (bio)molecules, which is very often carried out with the help of thiolate groups binding to the nanoparticle surface. 1 However, thiolate ligands have been shown to easily undergo exchange reactions with free thiol functions 2a-f which are usually present in biological media. It is a general observation that compounds with polydentate ligands are thermodynamically and kinetically more stable than those with an equivalent number of comparable monodentate ligands. Thus, ligands of the type RC(CH 2 S -) 3 , where R is a sufficiently long (w-functionalized) alkyl chain, could make use of the chelate effect to bind nearly irreversibly to the 2D surface or to the nanoparticle. The methylene linker allows flexible alignment of the headgroups whereas the whole geometry bears a high packing density on surfaces.One possible approach to the synthesis of surfactants of the type RC(CH 2 SH) 3 is the Tollens reaction with longchain aldehydes which results in the formation of triols of the type RC(CH 2 OH) 3 . 3 The conversion of the alcohol group into other functional groups, however, goes along with some difficulties. The tosylation of the triol 1a could be carried out in good yields, but the tosylate itself is very unreactive. Kolomyjec et al. correlated the reduced reactivity of such tritosylates with the neopentyl unit present in this structure. 4 The halogenation of the long-chain alcohol under different conditions is either not complete or causes decomposition as already found by Huttner in the case of 1b. 5 Treating the triol 1a with PBr 3 6,7 or with a mixture of P(OPh) 3 and PhBr in a modified MichaelisArbuzov reaction 8 did not produce the bromide but the bicyclic phosphite 2. By the simple addition of PBr 3 to 1 in diethylether the phosphite 2 can be synthesized in good yields and purity. 9 Its structure enables a high packing density, 10 and the phosphite headgroup is a better donor than the oxygen atom in phosphine oxides often used in nanoparticle syntheses. In first experiments we could show that well-stabilized cobalt particles can be prepared using the neutral ligand 2. 11 A more elaborate and selective way of C-O activation is the Mitsunobu reaction. 12 This reaction is a versatile tool for the replacement of an alcohol group by any nucleophile. We used...

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“…After removal of the solvent in vacuo, the crude product was fractionated at reduced pressure. The product, (CH 3 ) 3 Si-C᎐ ᎐ ᎐ C-CH 2 OCH 2 C(CH 2 Cl) 3 (9) was obtained as a colourless liquid. Yield: 2.38 g (7.87 mmol, 89%).…”

Section: Preparation Of (Ch 3 ) 3 Si-c᎐ ᎐ ᎐ C-ch 2 Och 2 C(ch 2 Cl) 3...mentioning

confidence: 99%

Tridentate phosphine ligands with novel linker-units

Findeis

Gade

2002

Dalton Trans.

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Ambiphile Tripod‐Komplexe: Synthese und Komplexchemie langkettiger funktionalisierter Tripod‐Liganden RC(CH₂PPh₂)₃ mit R = Pentyl oder 8‐Nonenyl

Cited by 21 publications

References 24 publications

XPS, FTIR-ATR, and AFM Structural Study of Silicon-Grafted Triol Monolayers for Controlled Anchoring of Single Molecule Magnets

XPS, FTIR-ATR, and AFM Structural Study of Silicon-Grafted Triol Monolayers for Controlled Anchoring of Single Molecule Magnets

Amphiphilic Trithiols RC(CH₂SH)₃

Tridentate phosphine ligands with novel linker-units

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Ambiphile Tripod‐Komplexe: Synthese und Komplexchemie langkettiger funktionalisierter Tripod‐Liganden RC(CH2PPh2)3 mit R = Pentyl oder 8‐Nonenyl

Cited by 21 publications

References 24 publications

XPS, FTIR-ATR, and AFM Structural Study of Silicon-Grafted Triol Monolayers for Controlled Anchoring of Single Molecule Magnets

XPS, FTIR-ATR, and AFM Structural Study of Silicon-Grafted Triol Monolayers for Controlled Anchoring of Single Molecule Magnets

Amphiphilic Trithiols RC(CH2SH)3

Tridentate phosphine ligands with novel linker-units

Contact Info

Product

Resources

About

Ambiphile Tripod‐Komplexe: Synthese und Komplexchemie langkettiger funktionalisierter Tripod‐Liganden RC(CH₂PPh₂)₃ mit R = Pentyl oder 8‐Nonenyl

Amphiphilic Trithiols RC(CH₂SH)₃