Carbohydrate-Responsive Surface Adhesion Based on the Dynamic Covalent Chemistry of Phenylboronic Acid- and Catechol-Containing Polymer Brushes

Article abstract of DOI:10.1002/anie.201711529

A glue, based on dynamic covalent chemistry, with a strong adhesion (2.38 kg cm^?2), water resistance and carbohydrate responsive reversibility is presented. Using surface initiated atom transfer radical polymerization (SI-ATRP), glass and silicon surfaces were coated with copolymers functionalized with phenylboronic acids and catechols. In combination with microcontact printing (μCP) these polymer brushes give access to a carbohydrate responsive “supramolecular Velcro”.

Full text of DOI:10.1002/anie.201711529

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Accepted Article
Title: Carbohydrate responsive surface adhesion based on dynamic
covalent chemistry of phenylboronic acid and catechol containing
polymer brushes
Authors: Sebastian Lamping, Tobias Otremba, and Bart Jan Ravoo
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using the Digital Object Identifier (DOI) given below. The VoR will be
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.201711529
Angew. Chem. 10.1002/ange.201711529
Link to VoR: http://dx.doi.org/10.1002/anie.201711529
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10.1002/anie.201711529
Angewandte Chemie International Edition
COMMUNICATION
Carbohydrate responsive surface adhesion based on dynamic
covalent chemistry of phenylboronic acid and catechol
containing polymer brushes**
Sebastian Lamping, Tobias Otremba, Bart Jan Ravoo*
Abstract: A glue based on dynamic covalent chemistry with strong
adhesion (2.38 kg cm-2) and carbohydrate responsive reversibility is
presented. Glass and silicon surfaces coated with copolymers
functionalized with phenylboronic acids and catechols using surface
initiated atom transfer radical polymerization (SI-ATRP) were
prepared. In combination with microcontact printing (µCP) these
responsive host-guest chemistry of cyclodextrin and ferrocene
was reported by Yan et al.[14]
Dynamic covalent chemistry (DCC) is a promising area of
supramolecular chemistry which is slowly entering materials
science.[15] This type of chemistry exploits covalent yet reversible
bonds, which are in a thermodynamic equilibrium and respond
readily to changes in composition. Established reactions for DCC
are the hydrazone and disulfide exchange as well as the self-
condensation of boronic acids with diols.[16] Soboczenski and
Edwards discovered the reaction of boronic acids with 1,2- and
1,3-diols in the middle of the 20th century.[17,18] The equilibrium
constant is determined by the geometry of the diol,[19] the pKa of
the boronic acid, and the pH of the solution.[20] The strongest
interactions are obtained by combining phenylboronic acids,
which have a low pKa, with catechol, which has a perfect geometry
for binding due to its rigid aromatic backbone. In literature several
examples of boronic acids as receptors or sensors for
carbohydrates can be found.[21-26] An alternative way for the use
of catechols and boronic acids in materials is the preparation of
polymers to obtain multivalent interactions. An interesting
approach was reported by Messersmith et al. who investigated a
pH responsive self-healing hydrogel by boronate-catechol
complexation.[27] At basic pH a hydrogel could be formed,
whereas in neutral pH the dynamic covalent bonds are broken.
Catechols were also used as co-monomers for surface coatings,
due to their good surface adhesion.[28,29] For the functionalization
of surfaces with specific polymer brushes containing catechol or
phenylboronic acids, controlled radical polymerization such as the
reversible addition-fragmentation chain transfer polymerization
(RAFT) or the atom transfer radical polymerization (ATRP) are
well explored.[30-32] Catechol-based initiators are often used for
ATRP, because they tend to bind strongly to a wide range of
surfaces.[33,34] Zhang et al. polymerized phenylboronic acids via
ATRP on iron oxide nanoparticles to enrich glycoproteins
selectively.[35] Ye et al. functionalized silica particles with boronic
acid functionalized polymer brushes by ATRP. Due to the
multivalency of the fluorescent boronic acid, they could identify
and separate carbohydrates.[36]
polymer brushes give access to
“supramolecular velcro".
a carbohydrate responsive
Nature is an endless source of inspiration for chemists. For
instance, there would be no higher organisms without recognition
processes based on non-covalent interactions that lead to cell
adhesion.
Similarly,
the development
of
biomimetic
supramolecular materials to either enhance adhesion or prevent
fouling plays an increasingly important role in research and
industry. Nature offers many examples of adhesion directed by
reversible supramolecular interactions. A gecko uses enhanced
van der Waals forces on its high surface area footpads to walk on
walls or ceilings.[1] Mussels stick on rocks and cliffs by hydrogen
bonding or metal-ligand complexes.[2] The challenge for
researchers is to transfer these nanoscale interactions into
macroscopic systems in order to develop innovative adhesives
based on supramolecular interactions. Amongst others, Xie et al.
glued an epoxy polymer to a sulfonated polystyrene polymer
using cation-π-interactions.[3] Weder et al. developed a light
switchable supramolecluar glue based on metal ion
coordination.[4] Another very well-studied adhesive is the mussel
inspired hydrogen bonding of L-3,4-dihydroxyphenylalanin
(DOPA).[5-9] A particularly interesting study is that of Lu et al. on
the so-called mussel foot protein. They combined the hydrogen
bonding of DOPA with interactions of amyloidogenic proteins to
yield strong underwater adhesion.[6] Yet another interesting
approach is the use of host-guest interactions to enable non-
covalent adhesion on surfaces.[10-14] Our group reported a strong
adhesion of two azobenzene functionalized surfaces and a β-
cyclodextrin polymer as a supramolecular glue.[12] Kim et al.
prepared
a redox-responsive water resistant velcro using
ferrocene and cucurbit[7]uril functionalized surfaces to achieve a
stable adhesion. When changing the oxidation state of ferrocene
by the addition of NaClO4 the binding affinity decreases and the
surfaces are released.[13] A similar concept exploiting the redox-
Herein we present
a
reversible, water resistant,
supramolecular glue based on DCC of phenylboronic acid and
catechol. An ATRP-initiator was immobilized by microcontact
printing (µCP) via the well-established triazolinedione (TAD)
37, 38]
click[12,
reaction to obtain patterns on glass and silicon
surfaces. Co-polymer brushes containing either phenylboronic
acid acrylate (PBAA) with hydroxyethyl acrylate (HEA) or catechol
acrylamide (CAA) with HEA were successfully synthesized in a
grafting-from approach by ATRP. The polymer brushes were
analyzed and characterized and the strength of the adhesion
between phenylboronic acid and catechol modified surfaces was
investigated. Due to the dynamic covalent nature the adhesive
can be released by adding a carbohydrate as a competitive binder
for the phenylboronic acid.
[*]
S. Lamping, Dr. T. Otremba, Prof. Dr. B.J. Ravoo
Organisch-Chemisches Institut and Center for Soft Nanoscience
Westfälische Wilhelms-Universität Münster
Corrensstr. 40, 48149 Münster, Germany
E-mail: b.j.ravoo@uni-muenster.de
[**]
This work was supported by the Deutsche Forschungs-
gemeinschaft (DFG SFB 858 and Ra1732/9).
Supporting information for this article is given via a link at the end of
the document.
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10.1002/anie.201711529
Angewandte Chemie International Edition
COMMUNICATION
Figure 1: Microcontact printing (µCP) of TAD-ATRP initiator on octenyltrichlorosilane SAM with subsequent surface-initiated atom transfer polymerization (SI-ATRP)
of either catechol (PCAA-PHEA) or phenylboronic acid (PPBAA-PHEA) polymer brushes.
Two monomers, phenylboronic acid acrylate (PBAA) and
catechol acrylamide (CAA), for the polymer brushes were
synthesized.[39] Details of the synthesis and analysis of the
monomers are provided in the supporting information (SI).
Octenyltrichlorosilane SAM functionalized surfaces were
prepared according to a literature procedure described in the SI.
The pre-functionalized alkene surfaces were reacted with a TAD-
ATRP initiator by microcontact printing (µCP) either with flat, non-
patterned poly(dimethyl siloxane) (PDMS) stamps or PDMS
stamps patterned with 5 µm lines. Afterwards the brushes
(PPBAA-PHEA or PCAA-PHEA) were polymerized in a grafting-
from approach by SI-ATRP (Fig. 1). In both cases, 15mol% of
CAA or PBAA was mixed with 85mol% of HEA. Details of the
preparation of the polymer brushes are provided in the SI. The
obtained brushes were analyzed concerning their composition
and height. The topography of the patterned surfaces was
measured by atomic force microscopy (AFM). The height of the
PPBAA-PHEA brushes was about 30 nm over a large area (Fig.
2a). A similar height was measured for the PCAA-PHEA brushes
with about 35 nm (Fig. 2b).
In addition, to visualize the copolymerization of
phenylboronic acid onto the surface, a glass substrate containing
the PPBAA-HEA brushes was incubated with Alizarin Red S
(ARS), a fluorogenic reporter molecule that luminesces only upon
binding to boronic acids.[20] In Figure 2c a fluorescence
microscopy image of the ARS incubated surface clearly showing
the patterned polymer brushes can be seen.
To determine the copolymer composition of PPBAA-PHEA
and PCAA-PHEA brushes, X-ray photoelectron spectroscopy
(XPS) measurements were done. The octenyltrichlorosilane
SAM, the printed TAD-ATRP initiator surfaces and the surfaces
with either PPBAA-PHEA or PCAA-PHEA brushes were
compared in a C 1s spectrum (Fig. 3a). All spectra show a typical
signal at a binding energy of 285.0 eV which belongs to the
aliphatic C-C bonds in the molecular layers. In comparison
between the octenyltrichlorosilane SAM (black) and the TAD-
ATRP surface (grey) a little shoulder appears due to the C-O and
C-N bonds in the TAD-ATRP (286.0 - 287.5 eV). After
polymerization of PPBAA-PHEA brushes (green) and PCAA-
PHEA brushes (blue) two new signals appear. The signal at a
binding energy of 286.7 eV is explained by the C-OH bonds in the
alcohol groups of the copolymerized HEA. The signal with the
highest binding energy of about 289.1 eV occurs due to the C-
OOR bonds in the carboxylic esters of the acrylic backbone. The
electron withdrawing oxygen atoms increase the binding energy
of inner shell electrons of the carbon atoms. In addition, to prove
the success of the copolymerization a B 1s and N 1s spectrum
was measured. The B1s spectrum shows a signal at 192.2 eV for
the PPBAA-PHEA brushes (green) (Fig. 3b), corresponding to the
B atom in the phenylboronic acid moiety whereas no signal for the
octenyltrichlorosilane SAM (black) appears. For the PCAA-PHEA
brushes (blue), a N 1s signal at 399.6 eV was detected which
indicates the N atom in the CAA monomer (Fig. 3c). No signal was
detected for the octenyltrichlorosilane SAM (black).
Figure 2: a) AFM image with corresponding height profile of PCAA-PHEA
brushes. b) AFM image with corresponding height profile of PPBAA-PHEA
brushes. c) Fluorescence microscopy image of a PPBAA-PHEA surface after
incubation with reporter dye ARS. Scale bar = 20 µm for AFM images and 50 µm
for fluorescence microscopy image.
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10.1002/anie.201711529
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Figure 4: a) Surface adhesion using phenylboronic acids and catechols: 1.
Activation by adding a drop of deionized water for 10 min. 2. Drying of the
surfaces with a tissue. 3. Contacting one surface in an orthogonal fashion to the
other with gentle pressure and drying for 30 min. b) Close-up of the adhering
surfaces and maximum weight test of non-patterned surfaces with 4 kg hanging
on the glued surfaces. c) Adhesion is water resistant for pattermed as well as
non-patterned surfaces.
Figure 3: XPS spectra of PPBAA-PHEA- and PCAA-PHEA-surfaces. a) XPS
spectrum of the C 1s signal from PPBAA-PHEA. Octenyltrichlorosilane SAM
(black), printed ATRP-initiator (grey) and PPBAA-PHEA brushes (green). b)
XPS spectrum of the C 1s signal from PCAA-PHEA. Octenyltrichlorosilane SAM
(black), printed ATRP-initiator (grey) and PCAA-PHEA brushes (blue). c) XPS
spectrum of the B 1s signal. Octenyltricholorosilane SAM (black) and PPBAA-
PHEA brushes (green). d) XPS spectrum of the
Octenyltrichlorosilane SAM (black) and PCAA-PHEA brushes (blue).
N
1s signal.
The maximum weight that could be attached to non-patterned
surfaces was more than 4 kg at a contact area of 1.68 cm2 which
converts to an adhesion strength of 2.38 kg cm-2. Importantly, if
two PPBAA-PHEA or two PCAA-PHEA or non-functionalized
surfaces were pressed together no adhesion was obtained.
To further prove that surface adhesion is based on dynamic
covalent bonds the reversibility of the glue was tested. To this
end, surfaces patterned with polymer brushes (5 µm line patterns,
see Fig. 2) were glued together in an orthogonal fashion and
maximum weight tests were prepared. When the glued surfaces
ruptured, they were sonicated in deionized water for 10 min, dried
in an argon stream and the gluing process with following
maximum weight test was repeated. For the first gluing an
average maximum weight of 3.17 kg (±0.23 kg) was reached. The
second gluing displays an average maximum weight of 2.47 kg
(±0.43 kg) while the third gluing held about 1.33 kg (±0.43 kg)
(Fig. S3). These weights convert to a decrease of the maximum
strength of 78% for the first and 53% for the second gluing step
which indicates the reusable supramolecular adhesion of PPBAA
and PCAA in the polymer brushes. Moreover the adhesion of the
third gluing step is still very strong compared to other
supramolecular velcros (see SI).[4,12,13] The loss of strength can
be explained by the fact that some polymer brushes will be ripped
out each time the glue ruptures and the buckling of polymer
brushes due to the applied pressure during the gluing process,
which leads to a higher density and less flexibility of the brushes.
Due to the dynamic covalent bonds a release of the glued
surfaces can likely be induced by addition of a competitive binder
such as D-fructose. To confirm this assumption first the water
stability of the dynamic covalent glue was studied. Two line-
patterned, adhering surfaces with an additional weight of 1.0 kg
were placed on a holder in water (Fig. 4c). The surfaces still held
tightly together after 18 h, which impressively proves the water
resistance of the dynamic covalent glue. However, when the
surfaces were placed in a 1.0 M solution of D-fructose with the
same additional weight, the surfaces where release within 30 min.
The most likely explanation for this observation is that the
A further proof for the successful polymerization is obtained
from NMR analysis of polymer strands polymerized in the same
batch as the surfaces in presence of a sacrificial co-initiator in
solution (Fig. S1, S2). The NMR spectra of the copolymers and
CAA monomer or PBAA monomer were compared. The typical
acrylate/acrylamide signals disappear whereas the aromatic
signals of the catechol and phenylboronic acid are clearly
observed. On the basis of these aromatic signals the monomer
ratio of CAA and HEA or PBAA and HEA could be determined.
The ratio of the PBAA to HEA was about 1 to 9.3 (10.7mol%)
which is a little lower than the used amount of PBAA monomer
(15mol%). For the other copolymer the ratio of CAA to HEA was
about 1 to 7.7 (12.9%) which is in a good agreement with the
expect ratio of 15mol%.
After characterization of the surfaces and polymer brushes
we investigated the adhesion of the functionalized surfaces. To
this end a PPBAA-PHEA surface and a PCAA-PHEA surface
where glued together by adding a drop of deionized water for
10 min to one of these surfaces, drying it with a tissue and gently
pressing it on top of the other one. The surfaces where pressed
together for a few seconds and left to dry for at least 30 min. A
small amount of water in between of the two surfaces was
necessary to obtain an optimal interaction medium and close
contact for the formation of dynamic covalent bonds. The flexible
polymer brushes should lead to multivalent binding and
compensation of surface irregularities. To measure how strongly
the surfaces adhere maximum weight test were performed. For
these weight tests patterned as well as non-patterned surfaces
(prepared by printing TAD-ATRP with either a patterned or a flat
PDMS stamp) were used. After gluing and drying, the surfaces
were attached to a holder and weights were added one after
another (Fig. 4). The gluing procedure can also be seen in a real
time video provided as SI (Movie S1).
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10.1002/anie.201711529
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COMMUNICATION
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In conclusion, we present a carbohydrate responsive and
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phenylboronic acids and catechols. By a SI-ATRP multivalent
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10.1002/anie.201711529
Angewandte Chemie International Edition
COMMUNICATION
COMMUNICATION
Sebastian Lamping,
Bart Jan Ravoo
Tobias Otremba,
Carbohydrate
responsive
surface
adhesion based on dynamic covalent
chemistry of phenylboronic acid and
catechol containing polymer brushes
Glue and release: A supramolecular glue was prepared through the combination of atom transfer radical polymerization and the
dynamic covalent chemistry of phenyl boronic acids and catechols. The glue shows strong adhesion (2.38 kg cm-2), is water
resistant, can be reused multiple times and releases in the presence of a carbohydrate.
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