Assignment #01:
Applications of organic compounds containing Boron and Silicon.
Submitted to:
MS. ROEYA REHMAN
Submitted by:
Group# 2
1. MCHEM01191076 Saman Akram
2. MCHEM01191047 Maryam Bashir
3. MCHEM01191022 Ali Amer
4. MCHEM01191093 MUHAMMAD JALIL
5. MCHEM01191127 Awais Mehmood
6. BSCHEM01171028 Ejaz Hussain
Course:
Heterocyclic and Organometallic Compounds
Application of organic compounds containing boron
Organoboron compounds have been playing an increasingly important role for organic synthesis,
functional molecules, functional polymers and biologically active agents. These compounds play
important role in carbohydrate chemistry. The discovery that diboron reacts practically
instantaneously with alkenes and related carbon compounds, to convert them into corresponding
organoboranes , created huge interest in organic synthesis.
Here are some examples of important applications of organoboranes.
1. Application of organoborane polymers:
Boron-containing polymers represent an emerging class of inorganic and organometallic
polymers . They have long been known for their unique properties, including flame
retardance and high thermal stability, and their use as preceramic materials.
More recently, applications as
electrolytes for lithium ion batteries and as
photo- and electro-active polymers (including holographic, nonlinear optical,
electroluminescent materials) have been explored.
Moreover, the attachment of Lewis acidic borane groups has been exploited for the development
of
supported reagents and immobilized catalysts,
separation media
sensor systems
stimuli-responsive materials
biomaterials
a. Borane Polymers as Lewis Acids and Anion Sensors
Among the earliest examples of polymer-supported borane Lewis acids are Merrifield resins
that were functionalized with 9-BBN or Tip2B moieties. The Lewis acidity of tricoordinate
organoborane polymers is also advantageous for the development of new luminescent materials
for the recognition and sensing of anions. . Figure shows selected examples of conjugated
organoborane polymers that are luminescent and at the same time act as Lewis acids.
These are the examples of conjugated organoborane polymers that were studied for the
recognition of anions and aromatic amines.
The block copolymer not only responds to fluoride anions with a color change but at the same
time the solubility characteristics change dramatically. In DMF solution, the borane-
functionalized block forms the core of self-assembled aggregates, but upon addition of a small
amount of fluoride anions the aggregates disassemble into individual polymer chains. The
disassembly process can be monitored by a change in turbidity as well as the quenching of the
fluorescence.
Figure#2 : Fluoride ion sensing with organoborane block copolymers
b. Luminescent Polymers Based on Boron Chelate Complexes:
Polymers that contain boron heterocycles, typically with boron in the tetracoordinate
state, have been pursued vigorously due to their promise as new luminescent materials.
Important applications are
emissive and electron-conduction materials for organic light emitting devices
(OLEDs), lasing materials,
in bioimaging,
stimuli-responsive materials.
Architectural control tends to be an important aspect because it allows for the
fabrication of controlled size nanoparticles, for example, by the assembly of block copolymers or
star polymer.
c. BODIPY-Functionalized Polymers:
Boron dipyrromethene dyes are among the most widely utilized fluorophores, because of
their strong and sharp emission in the visible and in some cases even the NIR region.
Numerous polymers have been developed with BODIPY as pendant groups or
incorporated into the polymer main chain.
d. Boronic and Borinic Acid-Functionalized Polymers for Biomedical Applications and
as Smart Materials:
Boronic acid-functionalized polymers have garnered intense interest because of the
ability of boronic acids to reversibly bind 1,2- or 1,3-diols .This property allows for the
detection and immobilization of sugars; especially the complexation of glucose is of great
importance in diagnostics and treatment of diabetes.
These compounds have great importance in (1) architectural control; (2) development of
multiple responsive systems; (3) structural modification to allow for application at
physiological pH; and (4) the discovery of new responsive materials.
2. Application in carbohydrate Chemistry
The reversible covalent interactions between organoboron compounds and diols have
been applied for many years in carbohydrate chemistry. They form the basis of efficient
methods for the detection of car-bohydrates, and applications in cellular imaging and
glycoprotein analysis are beginning to emerge.
a) Organoboron-based carbohydrate sensors:
Boronic acid probesoffer the key advantage of thermodynamically favorable
binding to carbohydrates in polar protic solvents, which typically competewith
binding of guests to hydrogen bonding-based receptors.
For example, the association constant between phenylboronic acid
and fructose is 210 M-1 in pH 7.5 phosphate buffer.
b) Applications of boronic acid–carbohydrate interactions in cellular imaging
and drug delivery:
The development of gastrointestinal, pancreatic, and breast cancers has been
linked with the overexpression of sLeX-containing mucins on cell [Link] an
effort to develop sensors capable of selectively identifying cells expressing the
sLeX antigen, the group of Wang explored a series of molecules contain-
ing two boronic acid moieties capable of binding to vicinal-diolstructural motifs
in sLeX, interspaced with a linker.
c) Organoboron compounds in carbohydrate separation
The ability to quantify components of mixtures of carbohydrates or glycated
proteins is needed for the diagnosis and study of such indications as diabetes,
cancer, Alzheimer’s disease, and autoimmune diseases. Because
monosaccharides generally do not differ greatly in polarity and lack chromophore
groups, the separation of mixtures of carbohydrate-derived analytes is often a
challenging task. Incorporation of boronic acid functionality to a chromatographic
stationary phase provides the opportunity for discrimination of carbohydrate-
derived analytes based on specific strong interactions.
Organoboron derivatives of several classes of materials, including cellulose,
polystyrene, polyacrylamides, and porous silica, have been employed for this
purpose.
Application of organosilicon compound
Organosilicon compounds are widely encountered in commercial products
. Most common are sealants, caulks (sealant), adhesives, and coatings made from silicones
. Other important uses include synthesis of polyhedral oligomeric silsesquioxanes
, agricultural and plant control adjuvants commonly used in conjunction
with herbicides and fungicides.
Silicone caulk, commercial sealants, are mainly composed of organosilicon compounds.
Biology and medicine
Carbon–silicon bonds are naturally absent in biology, however enzymes have been used to
artificially create carbon-silicon bonds in living microbes
Silicates, on the other hand, have known existence in diatoms.
Silafluofen is an organosilicon compound that functions as a pyrethroid insecticide.
Several organosilicon compounds have been investigated as pharmaceuticals.[
Silicon rubber
Silicon rubber are use as insulator
Silicon oil
Silicon oil are use in high temperature oil bath
Silicon grease : are use as lubricant
Other application: use for making water proof clothes and papers
And use for making paint and enamel
REFRENCES
1. [Link]
2. [Link]
3. [Link]
4. [Link]
5. [Link]
6. [Link]
