Group 1 ppt.pdf Applications of organometallic

Applications of Organometallic
compounds in Organic synthesis
Presented By: Group no. 01
Presented To: Dr. Sajjad Hussain Sumrra

Applications of Organometallic
compounds in Organic synthesis
Group no.01
i. Muneeba Shaheen(23017107-006)
ii. Rimsha Kousar(23017107-011)
iii. Khadija Bibi(23017107-005)
iv. Anfal Ashrif(23017197-009)
v. Amina Afzal(23017107-016)

Applications of Organometallic compounds
in Organic synthesis
Names Roll numbers Topics
Muneeba shaheen 23017107-006 Tris(8-
hydroxyquinoline)alumin
ium(III)/Alq3
applications in organic
synthesis
Rimsha kousar 23017107-011 Vaska’s complex
synthesis
Khadija bibi 23017107-005 Ziegler Natta catalyst
synthesis
Anfal Ashrif 23017107-009 Willinson’s complex
synthesis
Amina Afzal 23017107-016 Applications of Grignard
Reagent in organic

Applications/Uses of alq3 ( Tris(8-
hydroxyquinoline)aluminium(III) ):
Tris(8-hydroxyquinoline)aluminium(III))/Alq3

Introduction:
Tris(8-hydroxyquinoline)aluminium(III) is also known as Alq3.
The chemical formula of Alq3 is AI(C9H6NO)3 . Its molecular weight is
459.43g/mol. Widely abbreviated Alq3.
Alq3 is a chemical compound used in organic light emitting diodes (OLEDs) as an
electron transport material and emitting layer. It is widely used in organic
synthesis such as catalyst, reagent and photoluminescent material.
Alq3 is also known for its high thermal stability, high quantum yield of
fluorescence and high electron transport ability.

Method of preparation:
It is prepared by the reaction of 8-hydroxyquinoline and aluminium(III) in the
presence of OH _ ions.

Applications/uses in organic synthesis:
1. Catalyst:
Alq3 has been used as a catalyst in various organic reactions such as Ring-
opening polymerization, Aldol reactions and Michael additions.
Ring opening polymerization reaction:
Here is an example of ROP reaction where Aq3 (Tris(8-
hydroxyquinoline)aluminium(III)) is used as a catalyst.
ROP of E-caprolactone
Alq3 can be used as a catalyst for the ROP of E-caprolactone to produce
polycaprolactone (PCL), a biodegradable and biocompatible polymer.

Reaction Scheme:
E-caprolactone + (𝐴𝑙𝑞3)𝑛→ polycaprolactone
Rection:
Role of Alq3
Alq3 acts as a Lewis acid catalyst, coordinating with the E-caprolactone monomer and facilitating
the ring opening reaction. This leads to the formation of PCL with controlled molecular weight
and architecture.

2. Reagent:
Alq3 has been used as a reagent in organic synthesis, particularly in the
preparation of quinoline derivatives and heterocyclic compounds.
Quinoline Derivatives:
Tris(8-hydroxyquinoline)aluminium(III) is used a a reagent in the synthesis of
many quinoline derivatives.
It is also used to produce many useful and important agents/compounds such as
anti-cancer agent, anti-fungal agent, anti-bacterial agent, OLEDs, ion-
selective chemosensor for AI(III) etc.

hydroxyquinoline)aluminumIII ):
Reactions:

3. Photoluminescent material:
Alq3 is known for its photoluminescent properties and has been used in the
development of organic light emitting diodes(OLEDs) and photovoltaic devices.
Organic light emitting diodes(OLEDs)
Alq3 (Tris(8-hydroxyquinoline)aluminium(III)) is a photoluminescent material used
in OLEDs and photovoltaic devices as both an electron transport layer(ETL) and
an electron emitting layer(EML).
It is known for its high thermal stability, high quantum yieldof fluorescence and
good electron-transport ability.
In OLEDs Alq3 is often doped with other material to tune the emission color and
it can be combined with polymers for enhanced performance.

OLEDs:
❖ Electron Emitting Layer(EML)
Alq3 has ability to fluoresce green light makes it a popular choice for EMLs in
OLEDs, especially when green emission is required/desired.
Alq3 has inherent photoluminescence properties which makes it suitable for
generating light through electron hole recombination in OLEDs.
❖ Electron Transport Layer(ETL)
Alq3 also serves as an efficient electron transport material, facilitating the
movement of electrons within the device. Alq3 as an electron transport and
emitting layer material was the first efficient low molecular weight OLED
reported by Tang in 1987.

❖ Color Tuning
By incorporating Alq3 into different structures or doping it with other materials,
the emission color can be tuned from green to other wavelengths.
e.g. yellow emission Tris(8-hydroxyquinoline)aluminium(III) by the
incorporation of quantum dots for OLED.
We propose the use of zinc oxide quantum dots to tune the emission color of the
complex while maintaining the luminous efficiency. Hence tris(8-
hydroxyquinoline) aluminium-zinc oxide nanohybrids with different zinc oxide
quantum dots concentrations (10, 20 or 30wt.% ) were synthesized.
The results show that the increased level of zinc oxide quantum dots lead to a
decrease in crystallinity, double hump emission and a slight red shift in emission.
Also, at 20 and 30 wt.% of zinc quantum dots concentrations, yellow emission
was observed.

Applications/Uses of Vaska’s complex
in organic synthesis:
Introduction:
Vaska’s complex, the discovery of which credited to Angoletta in 1958
but named after the Estonian-American chemist Lauri Vaska after his
extensive characterization in 1962. It is an air stable 16-electron square
planar iridium(1) complex that readily undergoes oxidative addition with
a number of oxidants, acids and electrophiles generating an 18-electron
octahedral Ir(III)species.
Vaska’s complex also binds reversibly to molecular oxygen in a side-on
fashion as opposed to the end-on binding found with the iron
complex(haemoglobin).

Oxidative addition chemistry:

Applications of Vaska’s complex in organic synthesis:
1. Hydrosilylation:
Hydrosilylation using vaska’s complex in combination with tetramethyldisiloxane
(TMDS) or its polymeric counterpart (PMHS)has been used for chemoselective
reduction of tertiary amides and synthesis of alpha-substituted amines however
mild partial reduction of amides to O-silylated hemiaminals and downstream
activated C=N intermediates can be trapped by nucleophiles(figure 1).

2. One-pot reductive coupling of amides with Grignard reagent:
One-pot coupling of tertiary amides with Grignard reagent reported by
the Dixon group in 2017, in which alpha-amino arylation, alkene and
simple alkylation occur in high regioselectivity(figure2).

3. Chemoselective Synthesis of beta-Enaamino esters:
The second is the chemoselective reduction of beta-amido esters to the
corresponding beta-enamino ester, widely used synthetic building blocks in 2019
by Huang and Ye. Cyclic brta-amido esters were also reduced in this system to
give endocyclic beta-enamino esters such as the useful piperidine building block
shown below(figure 4).

4. Reductive Strecker-Type Reaction of Tertiary Amides and Lactams:
Finally Dixon and co-workers have developed a Reductive Strecker reaction using
Vaska’s complex in combination with TMDS and a cyanide source. The alpha-
aminonitrile products are precursors to the corresponding racemic amino acid,
though kinetic resolution using a nitrilase enzyme might expand the the scope of
this methodology(scheme 4).

5. Product of cyanation of the tertiary-amide in Flumazenil:
Late stage modification of the GABA-receptor antagonist Flumazenil was used to
demonstrate the applicability of the methodology in modification of complex
drug target(scheme 5).

Ziegler-Natta catalysts for polymerizing alkenes to make plastics like polyethylene
and polypropylene.
Applications of Ziegler Natta catalyst
Introduction
The Ziegler–Natta catalyst is a type of catalyst used in the
polymerization of alkenes (olefins), especially for producing
polyethylene and polypropylene. These catalysts revolutionized the
plastics industry by enabling the production of stereoregular
polymers, which have better mechanical and thermal properties

Types of Ziegler–Natta Catalysts
1. Heterogeneous CatalystsTypically based on titanium compounds (like TiCl₄)
supported on magnesium chloride (MgCl₂).Used with organoaluminum
compounds like triethylaluminum (Al(C₂H₅)₃) as co-catalysts.
2. Homogeneous CatalystsInvolve metallocenes (like zirconocene dichloride)
activated with methylaluminoxane (MAO).Allow very precise control over
polymer structure (single-site catalysts).
APPLICATIONS
Here are the main applications of Ziegler–Natta
catalysts---
. Polyethylene ProductionHigh-Density Polyethylene
(HDPE):Used for containers, pipes, bottles, toys, and
household goods.HDPE is strong, rigid, and has high
chemical resistance.

2. Polypropylene Production
Isotactic Polypropylene (i-PP):
A tough, crystalline polymer used in automotive parts, textiles, food containers,
and medical devices.Ziegler–Natta catalysts allow the formation of isotactic
(regular) structures with improved properties
3. Copolymerization of Olefins
Can create copolymers like ethylene-propylene rubber (EPR) and ethylene-
propylene-diene monomer (EPDM), which are widely used in automotive seals,
roofing, and insulation materials.

4. Stereoregular Polymers
Enable production of stereoregular polymers (like isotactic or
syndiotactic) with controlled crystallinity and mechanical properties.
---
5. Fiber and Film Applications
Used in making oriented films, fibers, and nonwoven fabrics due to
the strength and processability of the polymers produced.

Applications of zeise’s salt
Zeise’s salt, a well-known organometallic
compound. Zeise’s salt is potassium
trichloro(ethylene)platinate(II) with the chemical
formula K[PtCl₃(C₂H₄)]·H₂O.
Structure:
It contains a platinum (Pt) atom coordinated to three
chloride (Cl⁻) ions and an ethylene (C₂H₄) ligand.The
ethylene ligand is bound to the platinum via a π-complex,
where the π-electrons of the double bond interact with
the metal.

Zeise's salt is mainly used in academic and
research settings rather than in large-scale
industrial applications. Here are its key
applications:
1. Study of Metal–Alkene Bonding
2. Zeise’s salt is one of the earliest examples
of a metal-alkene π-complex, making it
essential for studying the nature of
metal-ligand interactions.It helps
understand π-backbonding and synergic
bonding in organometallic chemistry.
Applications of zeise’s salt

2. Teaching and Demonstration
Often used in chemistry education to demonstrate
concepts like:Coordination complexesOrganometallic
bondingCrystal field theory and spectroscopy
3. Catalysis Research
While Zeise's salt itself isn't a commercial catalyst, it serves as a
model compound for developing catalysts in:Homogeneous
catalysisOlefin polymerizationHydrogenation and hydroformylation
reactions

4. Structural and Spectroscopic Studies
Used as a benchmark compound in X-ray crystallography,
IR spectroscopy, and NMR to analyze metal-alkene
interactions.Helps in developing computational models
and theoretical chemistry studies.
5. Historical Importance
Zeise’s salt has historical significance in the development
of organometallic chemistry and is often cited in
retrospectives and academic literature.
APPLICATIONS OF ZEISE’S SALT

Group 1 ppt.pdf Applications of organometallic

A Grignard reagent is a highly reactive organometallic compound with the
general formula:
R–Mg–X
Where:
R = an alkyl, aryl, or vinyl group
X = a halogen (usually Cl, Br, or I)
Mg = magnesiumExample:CH₃MgBr – methylmagnesium bromide
APPLICATIONS OF GRIGNARD REAGENT
GRIGNARD REAGENT

Properties:
Highly reactive with water, CO₂, and oxygen –
must be handled under anhydrous
conditions.Acts as a nucleophile in reactions.

Uses:
Widely used in organic synthesis and pharmaceutical
chemistry.Important for making alcohols, acids, and other
functional groups.
Very important in organic synthesis for forming
carbon-carbon bonds, such as:
Adding to carbonyl compounds (like aldehydes
and ketones) to form alcohols.
Reacting with carbon dioxide to form carboxylic
acids.Forming complex alcohols, acids, and
hydrocarbons.
Sensitivity:
Reacts violently with water and oxygen, so
reactions must be done under anhydrous
conditions.

Group 1 ppt.pdf Applications of organometallic

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