Coating of polydopamine on polyurethane open cell foams to design soft structured supports for molecular catalysts

Article abstract of DOI:10.1039/c9cc05379d

Polydopamine-coated polyurethane open cell foams are used as structured supports for molecular catalysts through the covalent anchoring of alkoxysilyl arms by the catechol groups of the mussel-inspired layer. This strong bonding prevents their leaching. No alteration of the mechanical properties of the flexible support is observed after repeated uses of the catalytic materials.

Full text of DOI:10.1039/c9cc05379d

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L. Mendez Martinez, P. Bertani, T. Romero, D. Favier, T. Roland, V. Guidal, V. Bellieres-Baca, D. Edouard, L.
Jierry and V. Ritleng, Chem. Commun., 2019, DOI: 10.1039/C9CC05379D.
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Coating of polydopamine on polyurethane open cell foams to
design soft structured support for molecular catalysts
Ahmed Ait-Khouya,a Miguel L. Mendez Martinez,b Philippe Bertani,c Thierry Romero,d Damien
Favier,b Thierry Roland,b Valentin Guidal,e Virginie Bellière-Baca,e David Edouard,f Loïc Jierry,*b
and Vincent Ritleng*a,g
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
Polydopamine-coated polyurethane open cell foams are used as
In this context, we have recently developed an alternative
structured support for molecular catalysts through the covalent based on the use of open cell polyurethane foams (OCPUF).
anchoring of alkoxysilyl arms by the catechol groups of the These inexpensive foams present similar structural and
mussel-inspired layer. This strong bonding prevents their leaching. transport properties,2b with the advantage of being easily
No alteration of the mechanical properties of the flexible support engineered because of their lightweight and high mechanical
is observed after repeated uses of the catalytic materials.
flexibility.7 Inspired by a biomimetic approach based on the
mussels’ adhesion principle,8 we have shown that the whole
surface of this polymeric three-dimensional material can be
efficiently coated with an adhesive layer and further
functionalized with metallic or metal oxide NPs to get catalytic
properties.9 The process relies on catechol chemistry and
consists in coating a commercially available OCPUF with a layer
of polydopamine (PDA) by simple immersion in a buffered
aqueous solution of dopamine. Thanks to the adherence
properties of the catechol units,8 NPs can be easily grafted all
over the surface of the foam by simple dip-coating. In
particular, by using TiO2 NPs, we have designed a soft
structured supported photocatalyst, that can be used to
degrade water pollutants under batch or flow conditions.9
Moreover, thanks to the reducing properties of the catechol
units,10,11 M(0) NPs can be directly generated on the surface,
immobilized and stabilized,9a,11a,b which allows one to avoid
the usual high temperature reduction step to form metal(0)
NPs on classical supports. These properties give access to
OCPUF@PDA-supported multi-site heterogeneous catalysts.
Furthermore, thanks to the presence of catechol moieties
in the PDA structure, the covalent anchoring of molecular
catalysts bearing a group that can react with these, such as an
alkoxysilane, a chlorosilane, an amine or a thiol group should
also be possible.8,12 Herein, we show that OCPUF@PDA, can
indeed be functionalized with an organo- or an organometallic
catalyst bearing an alkoxysilyl arm. This approach gives access
to highly desirable OCPUF@PDA-supported single-site
heterogeneous catalysts and opens the gate to the use of the
large panel of catalysts reported for homogeneous catalysis.
According to our published procedure,9 cubic samples (4.5
cm3) of OCPUF (1) (20 PPI; Fig. S1- ESI) were coated with PDA
by simple immersion for 16 h at room temperature in an
aqueous solution of dopamine buffered to pH 8.5 (Fig. 1),
followed by thorough washings with deionized water. Low and
Continuous processes based on structured catalytic supports
are advantageous at the industrial scale. Structured supports
indeed display an important surface over volume ratio, and
allow efficient mass transfers and small pressure drops.1
Furthermore, they generate an intimate mixing of the reagents
and allow an easy separation of the catalyst from the reaction
products. Among the variety of structured catalytic supports,
open cell foams are prime candidates. Of ceramic or metallic
constitution, these host architectures are ideal supports for
catalytically active metallic nanoparticles (NPs).2 Thus, efficient
solid foam bed reactors have been reported, mainly based on
the coating of SiC or alumina foams with a catalytic phase.3
This kind of support have proven chemically robust for
catalytic reactions under harsh conditions, showing good
longevity,4 as well as enhancing the catalyst efficiency5 and
selectivity6 compared to other conventional supports. Their
expensive and energy consuming way of preparation however
represents an important drawback for their development,
especially when taking into account the current economic and
ecological constraints. Moreover, these foams are heavy and
difficult to handle, rigid and brittle, and present many closed
cells that can alter the reproducibility of the reactions.
a. Université de Strasbourg, Ecole européenne de Chimie, Polymères et Matériaux,
CNRS, LIMA, UMR 7042, 25 rue Becquerel, 67087 Strasbourg, France.
b. Université de Strasbourg, CNRS, Institut Charles Sadron, UPR 022, 23 rue du Loess,
67034 Strasbourg, France.
c. Université de Strasbourg, CNRS, Institut de Chimie, UMR 7177, 4 rue Blaise Pascal,
67081 Strasbourg, France.
d. Université de Strasbourg, Ecole européenne de Chimie, Polymères et Matériaux,
CNRS, ICPEES, UMR 7515, 25 rue Becquerel, 67087 Strasbourg, France.
e. Adisseo, Antony Parc 2, 10 place Général de Gaulle, 92160 Antony, France.
f. Univ Lyon, Université Claude Bernard Lyon 1, CNRS, LAGEPP, UMR 5007, 43
boulevard du 11 novembre 1918, F-69100 Villeurbanne, France.
g. Institut Universitaire de France, 1 rue Descartes, 75231 Paris, France.
Electronic Supplementary Information (ESI) available: Experimental procedures,
Figures S1-S16. See DOI: 10.1039/x0xx00000x
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DOI: 10.1039/C9CC05379D
Dopamine
(2 mg/mL)
DMAP-TES
(10 mg/mL)
TRIS
(10 mM, pH 8.5)
RT, 16 h
Toluene
70 °C, 24 h
OCPUF (1)
OCPUF@PDA (2)
OCPUF@PDA@DMAP (3)
500 ! m
150 ! m
50 ! m
Fig. 1
OCPUF coating with PDA and covalent functionalization with DMAP-TES.
Fig. 3
SEM images of OCPUF@PDA@DMAP (3) with different magnifications
high magnification scanning electron microscopy (SEM) images
of OCPUF@PDA (2) (Fig. S2) confirmed adsorption of PDA on
the whole surface of the resulting black three-dimensional
(3D) material as a continuous film with significant roughness,
as previously observed on 3D materials9,11 and flat surfaces.13
The soft structured support 2 was then functionalized with
4-{N-[3-(triethoxysilyl)propyl]-N-methyl-amino}pyridine14 (10
g/L) by condensation of the triethoxysilyl groups with the
catechol units of the PDA layer in toluene at 70 °C for 24 h. The
black colour of 2 clears up slightly, indicating a modification of
the coating (Fig. 1). The covalent anchoring of DMAP-TES to
the obtained OCPUF@PDA@DMAP material 3 was confirmed
by 29Si CP-MAS NMR spectroscopy. The NMR spectrum indeed
reveals signals at –67, –59 ppm and –53 ppm (Fig. 2A),
reminiscent of the T3, T2 and T1 substructures observed with
DMAP onto 2, rather than a strengthen Si signal in these
nodules. Hence, we expect that, the solvent, i.e. toluene, is
diffusing within the polyurethane material during the
silanization step, leading to a slight swelling of the foam, and
that the removal of the solvent under vacuum generates this
kind of “bubbles” on the surface of the foam. Accordingly a
decrease of about 3% of the foam mass was observed.
Compression tests (up to 30 % deformation) were then
performed on pristine 1, 2, and 3 to evaluate their chemical
resistance through their respective stress/strain responses
(Fig. 2B and S6). These measurements show typical hysteresis
loop for all three foams. The resulting Young modulus values
of 29.7 kPa for 1 and 33.3 kPa for 2 (Fig. S7) indicate that the
PDA deposition do not significantly modify the mechanical
properties of 2 compared to 1.9 These Young modulus values
also reveal a slightly lower stress response to the enforced
strain for 3 (18.5 kPa) compared to 1 and 2. As low-density
open cell foams mainly deform by bending of their cell edges,
a quadratic dependence on the relative density is usually
observed for the elastic modulus.15 Accordingly, calculation
demonstrated that the small reduction of the Young’s modulus
observed for 3 is due both to a lowering of the foam density by
about 3%, as measured experimentally, and to the induced
corrugated shape of the cell edges (Fig. S8 and S9).
The catalytic activity of 3 was next investigated for the
acylation of alcohols as a model reaction.16 Initial studies
focused on the acylation of benzyl alcohol (0.25 M) with 1.4
equivalent of acetic anhydride at 30 °C in the presence of 0.6
mol% of DMAP, DMAP-TES or DMAP moiety anchored onto
OCPUF@PDA in various solvents (Table 1). With DMAP, full
conversion to the acylated alcohol was observed after 3 h
reaction in n-hexane (entry 1). With DMAP-TES, only 84%
conversion was observed after 3 h in n-hexane (entry 2). Using
a 1:1 mixture of acetone and n-hexane instead, allowed
observing full conversion in 3 h with DMAP-TES as well (entry
3). This solvent was thus chosen for the rest of the study.
Satisfyingly, 3 allowed 81 % conversion after 3 h (TOF = 45 h-1
vs. 56 h-1 for DMAP in n-hexane; entries 1 and 4) and 97 %
after 19 h (entry 5). Control experiments with 1 and 2 showed
no conversion in both cases (entry 6), thus demonstrating that
it is well the immobilized DMAP moiety that catalyses the
acylation reaction. Furthermore, ICP-AES and HRMS analyses
of the reaction medium at the end of the acylation with 3
revealed no traces of silicon and no fragments of DMAP-TES,
which shows the absence of catalyst leaching. This was further
demonstrated by a stop-and-go experiment that showed that
the catalysis stops when 3 is removed from the reaction
medium, and re-starts when it is re-immersed (Fig. S10).
covalently anchored DMAP-TES on
a
silica matrix.14a
Inductively coupled plasma- atomic emission spectrometry
(ICP-AES) measurements on several samples of 3 revealed a
mean Si content of 4.44 g ± 0.59 g/kg (i.e. 0.158 ± 0.021
mol/kg). Low magnification SEM images reveal a slight
deformation of the struts whose edges become corrugated, as
well as the rough surface characteristic of the PDA coating.
Higher magnification images show the presence of
micrometric nodules randomly dispersed all over the surface
of the functionalized material 3 (Fig. 3 and S3), suggesting a
possible accumulation of DMAP in the latter. Elemental
mapping of Si by SEM-energy dispersive X-ray spectroscopy
(EDX) however revealed a relatively homogeneous distribution
of this element on the surface of 3 (Fig. S4 and S5), and thus of
4
(A)
(B)
OCPUF
OCPUF@PDA
OCPUF@PDA@DMAP
3
2
1
0
0
5
10
15
20
25
30
35
Strain ε (%)
Strain / %
!
(C)
(D) 3,5
3,0
! "#$%
!
! "#$%"'
"
! "( "' "
! "#$%"'
"
( ##"
! "&"'
"
RUN1
RUN5
. #"
- #"
, #"
+#"
%#"
*#"
) #"
&#"
( #"
#"
After RUN 5 and Agging Test
2,5
2,0
1,5
1,0
0,5
0,0
/ 01"( "
/ 01"&"
/ 01") "
/ 01"*"
/ 01"%"
0
5
10
15
20
25
30
35
Strain ε (%)
Strain / %
!
Fig. 2
(A) 29Si CP-MAS NMR spectrum of 3 (B) Stress/strain responses of 1 (violet), 2
(green), as-synthesized 3 (orange). (C) Acylation (%) of benzyl alcohol catalyzed by 3
after 24 h reaction for runs 1 to 5; average values obtained with 3 different foams. (D)
Stress/strain responses of one foam 3 used for the recycling tests after run 1 (pink), run
5 (green), and after the aging test (red).
2 | J. Name., 2012, 00, 1-3
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Table 1
Acylation of benzyl alcohol catalyzed by DMAP, DMAP-TES and 3.a
Table 2
Acylation of alcohols catalyzed by COPUF@PD#@DMAP (3).a,b
View Article Online
DOI: 10.1039/C9CC05379D
Conv. (%)c
Entry
Substrate
R
1
2
3
4
5
R = H
98
R = OMe
R = F
90
Entry
1
Catalyst
DMAP
Solvent
Time (h)
Conv. (%)b
TOF (h-1)c
93
99d
n-hexane
3
100
84
100
81
97
0
56
47
56
45
9
R = NH2
2
DMAP-TES n-hexane
3
3
DMAP-TES n-hexane/acetone
3
–
95
4 d,e
5 d,e
6 e,f
3
n-hexane/acetone
n-hexane/acetone
n-hexane/acetone
3
6
7
8
9
3
19
3
–
–
96
86
1 or 2
0
a Reaction conditions: benzyl alcohol (6.3 mmol), Ac2O (8.7 mmol), catalyst (0.6
mol%) in the solvent (25 mL) at 30 °C. b Conversions determined by 1H NMR. c TOF
values calculated from the conversions observed at the end of the reaction times
A cubic piece of 3, whose mass was adjusted to have 0.6 mol% of immobilized
DMAP-TES based on the Si content (i.e. 239 mg of 3 for 4.44 g Si/kg), was
–
–
96
50
d
e
a Reaction conditions: alcohol (6.3 mmol), Ac2O (8.7 mmol), catalyst (0.6 mol%) in
n-hexane/acetone (1:1) (25 mL) at 30 °C for 24 h. A single piece of 3, whose
immersed in the solution that was stirred at
Hexane/acetone ratio of 1:1. A cubic piece of 1 (224 mg) or 2 (226 mg) was
a
rate of 600 rpm.
n-
f
b
immersed in the solution that was stirred at a rate of 600 rpm.
mass was adjusted to have 0.6 mol% of immobilized DMAP-TES based on the Si
content (i.e. 239 mg of 3 for 4.44 g Si/kg), was immersed in the solution that was
stirred at a rate of 600 rpm. c Conversions determined by 1H NMR; average values
of two runs. A 7:3 mixture of p-aminobenzyl acetate and p-(acylamino)benzyl
acetate was formed.
The scope of the acylation reaction was then briefly
investigated with 3 in n-hexane/acetone (1:1) (25 mL) at 30 °C
for 24 h (Table 2). 98 % conversion to benzylacetate was
obtained under these conditions (entry 1). Both electron-rich
and electron-poor benzyl alcohols reacted well, giving
excellent conversions (entries 2 and 3). p- Aminobenzyl alcohol
was fully converted but provided a 7:3 mixture of p-
aminobenzyl acetate and p-(acylamino)benzyl acetate (entry
4). Phenol, furfuryl, allyl and cynnamyl alcoholswere all
converted to the corresponding acetates with good to
excellent yields (entries 5 to 8). The secondary alcohol,
cyclohexanol, gave only 50 % conversion (TOF = 3.5 h-1) (entry
9). This last result nevertheless compare advantageously with
that obtained with DMAP-TES functionalized mesoporous silica
nanospheres that required a catalytic charge of 7.5 mol%, a
temperature of 60 °C, as well as the presence of NEt3 to
achieve this acylation with a similar TOF of 4.8 h-1.14a
The reusability and chemical resistance of 3 was next
examined by carrying out five consecutive runs of benzyl
alcohol acylation under the conditions of Table 2. After run 1
and 5, 3 was removed from the reaction medium, washed with
n-hexane/acetone (1:1), dried under vacuum and submitted to
a stress/strain test. The goal of this analysis was to determine
the impact of successive immersions of 3 in an organic
medium at 30 °C on the mechanical properties of the
polymeric support. As shown in Figure 2C, the catalytic activity
remained remarkably constant during the five consecutive
runs. This was checked with three different foams.
Furthermore, the stress/strain response recorded after run 5
was similar to that recorded before the five runs and after run
1 (Fig. 2D), which shows that the mechanical properties of the
flexible catalytic material are not affected by its repeated use
in n-hexane and acetone, and in the presence of a corrosive
reagent such as acetic anhydride. Finally, to evaluate the
mechanical resistance of 3 over time, a fatigue test consisting
in compressing 3 5000 times to a strain of 30% (1 Hz) after run
5 was carried out (Fig. 2D). An almost unchanged Young
d
modulus (20.7 kPa) is observed for the artificially aged 3
compared to as-synthesized 3 (18.5 kPa), 3 after run 1 (18.7
kPa) and after run 5 (17.5 kPa) (Fig. S7), showing that 3,
overall, keeps its elastic properties overtime; a feature that
could allow to modulate the shape of the internal architecture
of the support through the application of an external
mechanical force that could reversibly deform the catalytic
bed in order to modulate/optimize the morphological
parameters of the foam and thus its transport properties. In
contrast to rigid open cell foams with fixed morphological
parameters and transport properties, using soft structured
foam could thus allow to tune these properties according to
the catalytic reaction needs. Furthermore, increased mass
transfer should be expected during compression/stretching
cycles.17 These considerations represent, we believe, a change
of paradigm in chemical engineering.
Encouraged by these results, we then decided to test
further the longevity of 3 by conducting 10 consecutive runs of
benzyl alcohol acylation of 3 to 19 h and then checking the
consequences of these runs on the PDA@DMAP layer by SEM.
Again, the activity was found to remain remarkably constant
overtime (Fig. S11). In agreement with this longevity, only
minor changes were observed at the surface. Thus, low
magnification SEM images of the so used 3 still show
corrugated edges, and higher magnification images still show
micrometric nodules, even though most of them have
vanished and a rough surface with dispersed nanometric
aggregates is now seen, as typically observed with PDA
coatings (Fig. S12).9,11,13
Finally, to establish the versatility of our approach to
design a soft structured support for molecular catalysts, we
next investigated the covalent anchoring of an organometallic
complex. For that purpose, we used the nickel-NHC complex 4
(Fig. 4 and Fig. S13–S17), whose analogues have been shown
This journal is © The Royal Society of Chemistry 20xx
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4
(10 mg/mL)
Toluene
70 °C, 24 h
Notes and references
OCPUF@PDA (2)
OCPUF@PDA@Ni(NHC) (5)
1
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Fig. 4
Covalent functionalization of OCPUF@PDA (2) with 4.
2
3
4
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Dalencon, WO 2016012689A2, 2016; (b) E. Pardieu N. T. T.
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Scheme 1. Hydrosilylation of benzaldehyde catalyzed by 4 and 5.
to efficiently catalyse the hydrosilylation of carbonyl
derivatives.18 Similarly than with DMAP-TES, 4 was grafted on
2 by condensation of its alkoxysilyl groups with the catechol
units of the PDA layer in toluene at 70 °C for 24 h (Fig. 4).
After characterization by SEM (Fig. S18), and assessment of
the nickel content by ICP-AES analyses of several samples of
OCPUF@PDA@Ni(NHC) (5) (4.24 g ± 0.49 g/kg, i.e.: 72.2 ± 8.3
mmol/kg), we carried out a brief catalytic study to establish
the possibility to also graft organometallic catalysts onto 2. For
that purpose, we investigated the catalytic activity of 5 (mass
adjusted to have 1 mol% of immobilized complex based on the
Ni content) for the hydrosilylation of benzaldehyde (0.04 M) in
THF at 25 °C with PhSiH3 (1.2 equiv.) as the hydrogen
source,17b and compared it to that of 4 (1 mol%) under similar
conditions (Scheme 1). After 22 h, 95% conversion to the silyl
ether was observed with 4 (TOF = 4.3 h-1) and 72% with 5 (TOF
= 3.3 h-1). This demonstrates the possibility to immobilize both
organo- and organometallic catalysts on OCPUF@PDA (2) and
thus to potentially access to a multitude of catalysts.
In summary, polydopamine has been used as an adhesive
layer on soft structured supports made of flexible
polyurethane open cell foams to covalently immobilize organo-
and organometallic catalysts through a silanization process.
This convergent grafting strategy, never reported onto PDA,
allows anchoring organo- and organometallic catalysts as long
as they are modified with suitable silane groups. This paves the
way to the access of a large panel of possible chemical
transformations. Furthermore, the ability of the mussel-
inspired coating to both bind tightly to the foam and form
strong covalent bonds with the molecular catalysts avoids
catalyst leaching into the medium. This property, combined to
the high chemical resistance of both the polyurethane foam
and the polydopamine layer, leads to easy-to-handle long-
living catalysts, as shown by the repeated uses of 3 and the
conservation of its mechanical properties. Thanks to its
lightweight, flexibility and low-pressure drop, such kind of soft
structured catalytic support thus appears as an ideal candidate
to design original flow chemistry2,4,19 or dynamic bed
reactors.17 This pioneering work, together with our previous
work that showed the possibility to also immobilize NPs,9
opens the way to a huge array of uses of 2 as a macroscopic
soft structured support for chemical engineering development.
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