from biosourced monomers to self assembly of graphene
TRANSCRIPT
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
From biosourced monomers
to self assembly of graphene based catalysts
aPolitecnico di Milano, Department of Chemistry, Materials and Chemical Engineering “G. Natta”
bDepartment of Chemistry and Applied Bioscience, ETH, Zurich, Switzerland
Maurizio Galimbertia
V. Barberaa, F. Margania, G. Prioglioa, D. Moscatellia, M. Sponchionia, U. Capasso Palmierob
MIPOL 2021 – Milan Polymer Days – July 6-8, 2021
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Items of the presentation
Biosourced Janus molecule
The functionalization of sp2 carbon allotropes
Waterborne nanoreactors
The nanoreactors for organic synthesis
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Politecnico di Milano, Department of Chemistry, Materials and Chemical Engineering “G. Natta”
ISCaMaP
Innovative Sustainable Chemistry and Materials and Proteins Group
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Politecnico di Milano, Department of Chemistry, Materials and Chemical Engineering “G. Natta”
ISCaMaP
Innovative Sustainable Chemistry and Materials and Proteins Group
Lucia Rubino
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Biosourced Janus molecule
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
2-(2,5-dimethyl-1H-pyrrol-1-yl) -1,3-propanediol
Serinol pyrrole - SP
A biosourced Janus molecule
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
A route for preparing serinol pyrrole. From glycerol
Propane-1,2,3-triol
easily available, cheap raw material
main by-product of bio-diesel production
not toxic
biodegradable
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
A route for preparing serinol pyrrole. From glycerol to serinol
2-Amino-1,3-propanediol
Propane-1,2,3-triol
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
A route for preparing serinol pyrrole. From serinol to serinol pyrrole
2-Amino-1,3-propanediol
Propane-1,2,3-triol
2-(2,5-dimethyl-1H-pyrrol-1-yl) -1,3-propanediol
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Δ
A route for preparing serinol pyrrole. From serinol to serinol pyrrole
Yield: at least 96%
Atom efficiency: 85%
Easy procedure
No solvent
By product: H2O
US10329253 B2; EP3154939 B1. V. Barbera, A. Citterio, M. Galimberti, G. Leonardi, R. Sebastiano, S. U. Shisodia, A. M. Valerio
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Δ
A route for preparing serinol pyrrole. From serinol to serinol pyrrole
From sp3 to sp2
Paal-Knorr reaction
US10329253 B2; EP3154939 B1. V. Barbera, A. Citterio, M. Galimberti, G. Leonardi, R. Sebastiano, S. U. Shisodia, A. M. Valerio
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Polyurethanes
Stepgrowth polymers based on serinolpyrrole
Polyethers
EP3180379 B1. M. Galimberti, V. Barbera, A. Truscello, R. Sebastiano, A. M. Valerio
V. Barbera, S. Musto, A. Citterio, L. Conzatti, M. Galimberti, eXPRESS Polymer Letters 2016, 10 (7) 548–558
M. Galimberti, V. Barbera, A. Citterio, R. Sebastiano, A. Truscello, A. M. Valerio, L. Conzatti, R. Mendichi, Polymer, 2015, 63, 62–70
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
The biosourced Janus molecule
and the functionalization of sp2 carbon allotropes
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
The graphitic substrate: nanographite
High surface area graphite (HSAG)
Surface area: 300 m2/g
Number of stacked layers: ca 35
WAXD Raman
Mauro M., Cipolletti V., Galimberti M., Longo P., Guerra G., J. Phys. Chem. C, 2012, 116, 24809−24813
50 nm
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Reaction of the pyrrole compound with an sp2 carbon allotrope
V. Barbera, L. Brambilla, M. Milani, A. Palazzolo, C. Castiglioni, A. Vitale, R. Bongiovanni, M. Galimberti, 2019. Nanomaterials, 9(1), p.44.
mixing and heating
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Reaction of the pyrrole compound with an sp2 carbon allotrope
V. Barbera, L. Brambilla, M. Milani, A. Palazzolo, C. Castiglioni, A. Vitale, R. Bongiovanni, M. Galimberti, 2019. Nanomaterials, 9(1), p.44.
mixing and heating
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Reaction of the pyrrole compound with an sp2 carbon allotrope
V. Barbera, L. Brambilla, M. Milani, A. Palazzolo, C. Castiglioni, A. Vitale, R. Bongiovanni, M. Galimberti, 2019. Nanomaterials, 9(1), p.44.
mixing and heating
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
31 2
Paal – Knorr Reaction
Carbocatalyzed Oxidation
Diels-Alder reaction
Carbon
allotrope
Domino reaction
Reaction of the pyrrole compound with an sp2 carbon allotrope
V. Barbera, L. Brambilla, M. Milani, A. Palazzolo, C. Castiglioni, A. Vitale, R. Bongiovanni, M. Galimberti, 2019. Nanomaterials, 9(1), p.44.
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Functional group:
from few % to 20%
Functionalization yield:
from 85% to quantitative
Covalent bond
between functional group
and carbon allotrope
Bulk structure of graphitic materials:
substantially unaltered
V. Barbera, A. Citterio, M. Galimberti, G. Leonardi, R. Sebastiano, S.U. Shisodia, A.M. Valerio. US10329253B2
M. Galimberti, V. Barbera, R. Sebastiano, A. Citterio, G. Leonardi, A.M. Valerio. US10160652B2
M. Galimberti, V. Barbera, R. Sebastiano, A. Truscello, A.M. Valerio. EP3180379B1
M. Galimberti, V. Barbera, EP3538511A1
M. Galimberti, V. Barbera, EP3538481A1
Mixing, energy
Carbon
allotropeA + B
Functionalized carbon allotropes
Mixing, energy
Carbon
allotropeA + B
Functionalized carbon allotropes
Reaction of the pyrrole compound with an sp2 carbon allotrope
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
a b c d e f g h
Conc (g/L): 10 5.0 2.5 1.0 0.50 0.25 0.10
HSAG
HSAG/SP
∼ 10 layers
Production of few layers graphene
M. Galimberti, V. Barbera, S. Guerra, L. Conzatti, C. Castiglioni, L. Brambilla, A. Serafini RSC Adv., 2015, 5, 81142-81152
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Graphene-based waterborne nanoreactors
for the confinement of organic synthesis
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Waterborne nanoreactors based on graphene layers
Why graphene layers?
High surface area
π – electron density
To avoid the use of toxic solvents
Why nanoreactors in water?
To carry out more sustainable reactions
To make reactions in confined space
To improve the yields
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Covalent
functionalization
with SP
Supramolecular
interaction
with
pyrrole containing
polymeric surfactants
micelles
The Nanoreactor
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Covalent
functionalization
with SP
Supramolecular
interaction
with
pyrrole containing
polymeric surfactants
micelles
Lipophilic microenvironment and catalytic component
Confined space
The Nanoreactor
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Amphiphilic block copolymers via RAFT polymerization
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Amphiphilic block copolymers via RAFT polymerization
5PEGMA950
CPAPEGMA950
Hydrophylic block
PEGMA950 = Poly(ethylene glycol)methyl ether methacrylate
CPA = 4-cyano-4 (phenylcarbonothioylthio)-pentanoic acid
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Amphiphilic block copolymers via RAFT polymerization
ethanol pyrrole
(EP)
methacryloyl
chloride EPMA
EPMA = 2-(2,5-dimethyl-1H-pyrrol-1-yl) ethyl methacrylate
The monomer for the lipophilic block
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
5PEGMA950-p(EPMA)
Amphiphilic block copolymers via RAFT polymerization
[[[ [
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
5PEGMA950-p(EPMA)
[[
[ [
Amphiphilic block copolymers via RAFT polymerization
5PEGMA950
p(EPMA)
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Just polymer Polymer/HSAG-SPPolymer/HSAG
0
100
200
300
400
Av
era
ge
pa
rtic
le s
ize [
nm
] 5 PEGMA - 5 EPMA
5 PEGMA - 10 EPMA
5 PEGMA - 20 EPMA
Formation of micelles
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
The adduct between 5PEGMA950-p(EPMA) and graphene layers
as nanoreactor for organic synthesis
The Dropcat catalyst
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Synthesis of imines with the Dropcat catalyst
Why imines?
They are involved in the synthesis of drugs.
e.g.: benzodiazepines, antimalarial
They can be used in vulcanization systems of tyre compounds
Large scale applications
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Synthesis of imines with the Dropcat catalyst
HSAG-SP
+
5PEGMA950-p(EPMA) Cat / Water
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
time (min) Selected system T (°C) Yield (%)
240 - 180 60
5 5PEGMA-5EPMA/HSAG-SP 25 98
Synthesis of imines with the Dropcat catalyst
U. Capasso Palmiero, M. Sponchioni, F. Margani, D. Moscatelli, M. Galimberti, V. Barbera Small, 16(40), 2001207 (2020)
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
5PEGMA-5EPMA
What is the role of the monomer?
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5PEGMA-10TMAEMA
What is the role of the monomer?
5PEGMA-5EPMA
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
PU-SP
5PEGMA-10TMAEMA
What is the role of the monomer?
Mn = 1430 Da
5PEGMA-5EPMA
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Selected system Yield (%)
98
5PEGMA-TMAEMA/HSAG-SP 23
PU-SP/HSAG-SP 52
5PEGMA-5EPMA/HSAG-SP
Temperature = 25°C
time = 5 minutes
The role of the monomer. Dropcat catalysts with different polymers
U. Capasso Palmiero, M. Sponchioni, F. Margani, D. Moscatelli, M. Galimberti, V. Barbera Small, 16(40), 2001207 (2020)
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
The role of graphene layers. Dropcat catalysts with pristine nanographite
Selected system Yield (%)
-
5PEGMA-TMAEMA/HSAG 30
PU-SP/HSAG 50
5PEGMA-5EPMA/HSAG
U. Capasso Palmiero, M. Sponchioni, F. Margani, D. Moscatelli, M. Galimberti, V. Barbera Small, 16(40), 2001207 (2020)
Temperature = 25°C
time = 5 minutes
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
The role of graphene layers. Dropcat catalysts without graphene layers
Selected system Yield (%)
10
5PEGMA-TMAEMA 23
PU-SP 53
5PEGMA-5EPMA
U. Capasso Palmiero, M. Sponchioni, F. Margani, D. Moscatelli, M. Galimberti, V. Barbera Small, 16(40), 2001207 (2020)
Temperature = 25°C
time = 5 minutes
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
time (min) Selected system T (°C) Yield (%)
240 - 180 60
5 5PEGMA-5EPMA 25 10
5 5PEGMA-5EPMA/HSAG 25 -
5 5PEGMA-5EPMA/HSAG-SP 25 98
The synergy of covalent and supramolecular functionalization
U. Capasso Palmiero, M. Sponchioni, F. Margani, D. Moscatelli, M. Galimberti, V. Barbera Small, 16(40), 2001207 (2020)
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
EPMA based polymer reusability
Recyclability and catalytic activity
5PEGMA-5EPMA/HSAG-SP
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Drop Cat as self assembled nanoreactor
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
GelAerogel
Powder
Conclusions
Biosourced Janus molecule
The functionalization of sp2 carbon allotropes
Waterborne nanoreactors
The nanoreactors for organic synthesis in water
98% yield @25°C, 5 min
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Perspectives
Few layers of nanographene
importance of covalent functionalization
Adsorption of pyrrole compound
role of - interactions
Formation of micelles
Role of water solvent
Theoretical study based on Molecular Mechanics
and Molecular Dynamics simulations of:
Raffaini, G.; Ganazzoli, F. Macromol. Biosci. 2007, 7, 552.Understanding the performance of biomaterials through molecular modeling: Crossing the bridge between their intrinsic properties and the surface adsorption of proteins
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Acknowledgments
Maria Farina and Giulio Natta
Gianfranco Savino, Enrico Valentini (Politecnico di Milano)
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M. Galimberti et al - From biosourced monomers MIPOL 2021 Milano (I) July 6-8, 2021
Thanks
for your attention!
instagram: @ismaterials.polimi