Octadecyltrimethoxysilane

Last updated
Octadecyltrimethoxysilane
Octadecyltrimethoxysilane.png
Names
Preferred IUPAC name
Trimethoxy(octadecyl)silane
Other names
n-Octadecyltrimethoxysilane
Trimethoxyoctadecylsilane
Identifiers
3D model (JSmol)
AbbreviationsOTMS
5791830
ChemSpider
ECHA InfoCard 100.019.400 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 221-339-2
MeSH n-Octadecyltrimethoxysilane
PubChem CID
UNII
  • InChI=1S/C21H46O3Si/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(22-2,23-3)24-4/h5-21H2,1-4H3
    Key: SLYCYWCVSGPDFR-UHFFFAOYSA-N
  • InChI=1/C21H46O3Si/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(22-2,23-3)24-4/h5-21H2,1-4H3
  • CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC
  • O(C)[Si](OC)(OC)CCCCCCCCCCCCCCCCCC
Properties
C21H46O3Si
Molar mass 374.681 g·mol−1
AppearanceColorless liquid
Density 0.883 g cm−3
Melting point 16 to 17 °C (61 to 63 °F; 289 to 290 K)
Boiling point 170 °C (338 °F; 443 K)
1.438-1.44
Hazards [1]
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
2
1
0
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Octadecyltrimethoxysilane (OTMS) is an organosilicon compound. This colorless liquid is used for preparing hydrophobic coatings and self-assembled monolayers. It is sensitive toward water, irreversibly degrading to a siloxane polymer. [2] It places a C18H39SiO3 "cap" on oxide surfaces. The formation of OTMS monolayers is used for converting hydrophilic surfaces to hydrophobic surfaces, e.g. for use in certain areas of nanotechnology and analytical chemistry.

Contents

See also

Related Research Articles

Hydrophobe Molecule or surface that has no attraction to water

In chemistry, hydrophobicity is the physical property of a molecule that is seemingly repelled from a mass of water. In contrast, hydrophiles are attracted to water.

Surface science Study of physical and chemical phenomena that occur at the interface of two phases

Surface science is the study of physical and chemical phenomena that occur at the interface of two phases, including solid–liquid interfaces, solid–gas interfaces, solid–vacuum interfaces, and liquid–gas interfaces. It includes the fields of surface chemistry and surface physics. Some related practical applications are classed as surface engineering. The science encompasses concepts such as heterogeneous catalysis, semiconductor device fabrication, fuel cells, self-assembled monolayers, and adhesives. Surface science is closely related to interface and colloid science. Interfacial chemistry and physics are common subjects for both. The methods are different. In addition, interface and colloid science studies macroscopic phenomena that occur in heterogeneous systems due to peculiarities of interfaces.

A monolayer is a single, closely packed layer of atoms, molecules, or cells. In some cases it is referred to as a self-assembled monolayer. Monolayers of layered crystals like graphene and molybdenum disulfide are generally called 2D materials.

Self-assembly

Self-assembly is a process in which a disordered system of pre-existing components forms an organized structure or pattern as a consequence of specific, local interactions among the components themselves, without external direction. When the constitutive components are molecules, the process is termed molecular self-assembly.

Colloidal gold Suspension of gold nanoparticles in a liquid

Colloidal gold is a sol or colloidal suspension of nanoparticles of gold in a fluid, usually water. The colloid is usually either wine-red coloured or blue/purple . Due to their optical, electronic, and molecular-recognition properties, gold nanoparticles are the subject of substantial research, with many potential or promised applications in a wide variety of areas, including electron microscopy, electronics, nanotechnology, materials science, and biomedicine.

Self-assembled monolayer

Self-assembled monolayers (SAM) of organic molecules are molecular assemblies formed spontaneously on surfaces by adsorption and are organized into more or less large ordered domains. In some cases molecules that form the monolayer do not interact strongly with the substrate. This is the case for instance of the two-dimensional supramolecular networks of e.g. perylenetetracarboxylic dianhydride (PTCDA) on gold or of e.g. porphyrins on highly oriented pyrolitic graphite (HOPG). In other cases the molecules possess a head group that has a strong affinity to the substrate and anchors the molecule to it. Such a SAM consisting of a head group, tail and functional end group is depicted in Figure 1. Common head groups include thiols, silanes, phosphonates, etc.

Langmuir–Blodgett trough Laboratory equipment

A Langmuir–Blodgett trough is a laboratory apparatus that is used to compress monolayers of molecules on the surface of a given subphase and measures surface phenomena due to this compression. It can also be used to deposit single or multiple monolayers on a solid substrate.

Langmuir–Blodgett film Thin film obtained by depositing multiple monolayers onto a surface

A Langmuir–Blodgett (LB) film is a nanostructured system formed when Langmuir films—or Langmuir monolayers (LM)—are transferred from the liquid-gas interface to solid supports during the vertical passage of the support through the monolayers. LB films can contain one or more monolayers of an organic material, deposited from the surface of a liquid onto a solid by immersing the solid substrate into the liquid. A monolayer is adsorbed homogeneously with each immersion or emersion step, thus films with very accurate thickness can be formed. This thickness is accurate because the thickness of each monolayer is known and can therefore be added to find the total thickness of a Langmuir–Blodgett film.

Ultrahydrophobicity Material property

Ultrahydrophobic surfaces are highly hydrophobic, i.e., extremely difficult to wet. The contact angles of a water droplet on an ultrahydrophobic material exceed 150°. This is also referred to as the lotus effect, after the superhydrophobic leaves of the lotus plant. A droplet striking these kinds of surfaces can fully rebound like an elastic ball. Interactions of bouncing drops can be further reduced using special superhydrophobic surfaces that promote symmetry breaking, pancake bouncing or waterbowl bouncing.

Coffee ring effect

In physics, a "coffee ring" is a pattern left by a puddle of particle-laden liquid after it evaporates. The phenomenon is named for the characteristic ring-like deposit along the perimeter of a spill of coffee. It is also commonly seen after spilling red wine. The mechanism behind the formation of these and similar rings is known as the coffee ring effect or in some instances, the coffee stain effect, or simply ring stain.

Hydrophobin

Hydrophobins are a group of small cysteine-rich proteins that are expressed only by filamentous fungi that are lichenized or not. They are known for their ability to form a hydrophobic (water-repellent) coating on the surface of an object. They were first discovered and separated in Schizophyllum commune in 1991. Based on differences in hydropathy patterns and biophysical properties, they can be divided into two categories: class I and class II. Hydrophobins can self-assemble into a monolayer on hydrophilic:hydrophobic interfaces such as a water:air interface. Class I monolayer contains the same core structure as amyloid fibrils, and is positive to Congo red and thioflavin T. The monolayer formed by class I hydrophobins has a highly ordered structure, and can only be dissociated by concentrated trifluoroacetate or formic acid. Monolayer assembly involves large structural rearrangements with respect to the monomer.

The Vroman effect, named after Leo Vroman, describes the process of competitive protein adsorption to a surface by blood serum proteins. The highest mobility proteins generally arrive first and are later replaced by less mobile proteins that have a higher affinity for the surface. The order of protein adsorption also depends on the molecular weight of the species adsorbing. Typically, low molecular weight proteins are displaced by high molecular weight protein while the opposite, high molecular weight being displaced by low molecular weight, does not occur. A typical example of this occurs when fibrinogen displaces earlier adsorbed proteins on a biopolymer surface and is later replaced by high molecular weight kininogen. The process is delayed in narrow spaces and on hydrophobic surfaces, fibrinogen is usually not displaced. Under stagnant conditions initial protein deposition takes place in the sequence: albumin; globulin; fibrinogen; fibronectin; factor XII, and HMWK.

Molecular self-assembly Molecules adopt a defined arrangement without guidance or management from an outside source

Molecular self-assembly is the process by which molecules adopt a defined arrangement without guidance or management from an outside source. There are two types of self-assembly. These are intramolecular self-assembly and intermolecular self-assembly. Commonly, the term molecular self-assembly refers to intermolecular self-assembly, while the intramolecular analog is more commonly called folding.

Janus particles Type of nanoparticle or microparticle

Janus particles are special types of nanoparticles or microparticles whose surfaces have two or more distinct physical properties. This unique surface of Janus particles allows two different types of chemistry to occur on the same particle. The simplest case of a Janus particle is achieved by dividing the particle into two distinct parts, each of them either made of a different material, or bearing different functional groups. For example, a Janus particle may have one-half of its surface composed of hydrophilic groups and the other half hydrophobic groups, the particles might have two surfaces of different color, fluorescence, or magnetic properties. This gives these particles unique properties related to their asymmetric structure and/or functionalization.

A model lipid bilayer is any bilayer assembled in vitro, as opposed to the bilayer of natural cell membranes or covering various sub-cellular structures like the nucleus. They are used to study the fundamental properties of biological membranes in a simplified and well-controlled environment, and increasingly in bottom-up synthetic biology for the construction of artificial cells. A model bilayer can be made with either synthetic or natural lipids. The simplest model systems contain only a single pure synthetic lipid. More physiologically relevant model bilayers can be made with mixtures of several synthetic or natural lipids.

Silanization of silicon and mica is the coating of these materials with a thin layer of self assembling units.

Evaporation suppressing monolayers

Evaporation suppressing monolayers are materials that when applied to the air/water interface, will spread and form a thin film across the surface of the water. The purpose of these materials is to reduce evaporative water loss from dams and reservoirs.

Icephobicity is the ability of a solid surface to repel ice or prevent ice formation due to a certain topographical structure of the surface. The word “icephobic” was used for the first time at least in 1950; however, the progress in micropatterned surfaces resulted in growing interest towards icephobicity since the 2000s.

Nanosphere lithography (NSL) is an economical technique for generating single-layer hexagonally close packed or similar patterns of nanoscale features. Generally, NSL applies planar ordered arrays of nanometer-sized latex or silica spheres as lithography masks to fabricate nanoparticle arrays. NSL uses self-assembled monolayers of spheres as evaporation masks. These spheres can be deposited using multiple methods including Langmuir-Blodgett, Dip Coating, Spin Coating, solvent evaporation, force-assembly, and air-water interface. This method has been used to fabricate arrays of various nanopatterns, including gold nanodots with precisely controlled spacings.

Liquid marbles

Liquid marbles are non-stick droplets wrapped by micro- or nano-metrically scaled hydrophobic, colloidal particles ; representing a platform for a diversity of chemical and biological applications. Liquid marbles are also found naturally; aphids convert honeydew droplets into marbles. A variety of non-organic and organic liquids may be converted into liquid marbles. Liquid marbles demonstrate elastic properties and do not coalesce when bounced or pressed lightly. Liquid marbles demonstrate a potential as micro-reactors, micro-containers for growing micro-organisms and cells, micro-fluidics devices, and have even been used in unconventional computing. Liquid marbles remain stable on solid and liquid surfaces. Statics and dynamics of rolling and bouncing of liquid marbles were reported. Liquid marbles coated with poly-disperse and mono-disperse particles have been reported. Liquid marbles are not hermetically coated by solid particles but connected to the gaseous phase. Kinetics of the evaporation of liquid marbles has been investigated.

References

  1. "Octadecyltrimethoxysilane". pubchem.ncbi.nlm.nih.gov. Retrieved 5 December 2021.
  2. P. Fontaine; F. Rondelez (1995). J. Daillant; P. Guenoun; C. Marques; P. Muller; J. Tran Thanh Van (eds.). Kinetics of Polymerisation in Langmuir Monolayers of n-Alkyltrimethoxysilane. Short and Long Chains at Interfaces.

Further reading