116129-34-1

Usage

Uses

Used in Biomedical Applications:
11-Bromo-1-undecanethiol is used as a protective SAM on gold nanoparticles for the fabrication of in vivo sensors. This allows for the development of advanced medical devices that can monitor and respond to various biological processes within the body.
Used in Gasotransmitter Synthesis:
11-Bromo-1-undecanethiol is used as a component in the synthesis of gasotransmitters when mixed with dodecanethiol. This mixture can be coated on gold nanoparticles, enabling the creation of novel compounds with potential applications in various industries, including pharmaceuticals and environmental science.

Upstream product

• 947150-46-1 S-(11-bromoundecyl) ethanethioate 
• 16696-65-4 1,11-dibromoundecane 
• 7766-50-9 1-undecen-11-ylbromide 

Downstream Products

• 1331961-28-4 4,4'-[dithiobis(undecane-11,1-diyloxy)]bis{[N,N-bis(2-pyridylmethyl)aminomethyl]benzene} 
• 180133-73-7 4,4'-[dithiobis(undecane-11,1-diyloxy)]dibenzaldehyde 

Relevant academic research and scientific papers

Dual-responsive nanoparticles that aggregate under the simultaneous action of light and CO2

Metallic nanoparticles co-functionalised with monolayers of UV- and CO2-sensitive ligands were prepared and shown to respond to these two types of stimuli reversibly and in an orthogonal fashion. The composition of the coating could be tailored

Controlled Fabrication of Gold/Polymer Nanocomposites with a Highly Structured Poly(N-acylethylenimine) Shell

Two families of well-defined organic-inorganic nanocomposites have been synthesized either by attachment of an initiator as a capping self-assembled monolayer on a gold cluster onto which a macromolecule is grown in situ or by preformation of a defined polymer, followed by covalent or adsorptive attachment to a surface-capped metal cluster. The characteristics of these composites are compared in size and local organization. Possessing nanometer-sized gold clusters at the core and poly(N-acylethylenimine) chains radially or tangentially connected to the core, the resulting materials were characterized by TEM, GPC, UV, IR, NMR, and XPS spectroscopies. Larger particles with narrower polydispersity were obtained by in situ growth of the polymer on a preformed metal cluster, with best results being attained with a mixture of brominated and nonbrominated thiols in which steric accessibility to the initiator sites is varied.

Synthesis of nitric oxide-releasing gold nanoparticles

We report the synthesis of nitric oxide-releasing gold nanoparticles formed by place-exchange reaction of hexanethiol monolayer-protected clusters with diamine nitric oxide donor precursor molecules, which are subsequently converted to N-diazeniumdiolate NO donors. The nitric oxide release from the N-diazeniumdiolate-modified gold nanoparticles is tunable by varying the number and/or the chemical structure of the exchanged amine ligands. The size and stability of NO-releasing nanoparticles may prove useful for a range of biomedical and pharmaceutical applications. Copyright

"Click" synthesis of thermally stable au nanoparticles with highly grafted polymer shell and control of their behavior in polymer matrix

Thermally stable core-shell gold nanoparticles (Au NPs) with highly grafted polymer shells were synthesized by combining reversible addition-fragmentation transfer (RAFT) polymerization and click chemistry of copper-catalyzed azide-alkyne cycloaddition (CuAAC). First, alkyne-terminated poly(4-benzylchloride-b-styrene) (alkyne-PSCl-b-PS) was prepared from the alkyne-terminated RAFT agent. Then, an alkyne-PSCl-b-PS chain was coupled to azide-functionalized Au NPs via the CuAAC reaction. Careful characterization using FT-IR, UV-Vis, and TGA showed that PSCl-b-PS chains were successfully grafted onto the Au NP surface with high grafting density. Finally, azide groups were introduced to PSCl-b-PS chains on the Au NP surface to produce thermally stable Au NPs with crosslinkable polymer shell (Au-PSN3-b-PS 1). As the control sample, PS-b-PSN3-coated Au NPs (Au-PSN3-b-PS 2) were made by the conventional "grafting to" approach. The grafting density of polymer chains on Au-PSN3-b-PS 1 was found to be much higher than that on Au-PSN3-b-PS 2. To demonstrate the importance of having the highly packed polymer shell on the nanoparticles, Au-PSN 3-b-PS 1 particles were added into the PS and PS-b-poly(2- vinylpyridine) matrix, respectively. Consequently, it was found that Au-PSN 3-b-PS 1 nanoparticles were well dispersed in the PS matrix and PS-b-P2VP matrix without any aggregation even after annealing at 220 °C for 2 days. Our simple and powerful approach could be easily extended to design other core-shell inorganic nanoparticles.

Phosphorus Pentasulfide Mediated Conversion of Primary Carbamates into Thiols

In this paper, we report a method for the conversion of primary carbamates into thiols in the presence of phosphorus pentasulfide (P 2 S 5) in refluxing toluene. Presently, no method exists in the literature for conversion of carbamates into thiols and, to the best of our knowledge, it is the first report for this type of conversion. This method presents an indirect route for the conversion of alcohols into thiols via their carbamate derivatives that may be useful in the total synthesis of compounds containing a thiol functionality.

Immobilized aza-bis(oxazoline) copper catalysts on alkanethiol self-assembled monolayers on gold: Selectivity dependence on surface electronic environments

Aza-bis(oxazoline) copper complexes have been immobilized onto alkanethiol self-assembled monolayers on gold utilizing five background tail groups with different electronic characteristics. The catalyst was tested in the standard cyclopropanation reaction of ethyl diazoacetate and styrene. The five different tail groups were hydroxyl, bromine, carboxylic acid, ester, and nitrile. Enantioselectivity improved to 95% when the surrounding tail groups were hydroxyl- and bromine-terminated surfaces. The carboxylic acid and ester tail groups reduced the enantioselectivity compared to the homogeneous phase. Additionally, the homogeneous cyclopropanation reaction was performed in methanol, acetonitrile, ethyl acetate, and acetic acid to determine whether similar trends in selectivity could be obtained by varying the homogenous electronic environment. However, the cyclopropanation reaction in these solvents gave greatly reduced selectivity and yield of the cyclopropane products demonstrating the positive aspects of immobilization of self-assembled monolayer supports.

Remarkable high-yielding chemical modification of gold nanoparticles using uncatalyzed click-type i ,3-dipolar cycloaddition chemistry and hyperbaric conditions

Azide-terminated alkyl thiolate monolayer-protected gold nanoparticles (1-C,12MPN) with a core size of 1.8 ± 0.2 nm were prepared. 1-C,12MPN was modified in high yields via an uncatalyzed 1,3-dipolar cycloaddition (clicktype reaction) with a variety of terminal acyl alkynes under hyperbaric conditions at 11 000 atm. The resulting 1,2,3-tria- zole modified MPNs (2-C,12MPN) were characterized using 1H NMR spectroscopy and were verified by comparison of the spectra to those obtained for the products of the model reactions of 1-azidododecane with the same alkynes. TEM analysis showed that the high-pressure conditions did not affect the size of the gold core, suggesting that the only effect is to facilitate the chemical reaction on the particles.

NITRIC OXIDE-RELEASING PARTICLES FOR NITRIC OXIDE THERAPEUTICS AND BIOMEDICAL APPLICATIONS

The presently disclosed subject matter relates to nitric oxide-releasing particles for delivering nitric oxide, and their use in biomedical and pharmaceutical applications.