Electrochemically driven host-guest interactions on patterned donor/acceptor self-assembled monolayers

Article abstract of DOI:10.1039/c8cc00494c

Here, on ITO//Au patterned substrates SAMs of ferrocene (Fc) on the Au regions and of anthraquinone (AQ) on the ITO areas are prepared, exhibiting three stable redox states. Furthermore, by selectively oxidizing or reducing the Fc or AQ units, respectively, the surface properties are locally modified. As a proof-of-concept, such a confinement of the properties is exploited to locally form host-guest complexes with β-cyclodextrin on specific surface regions depending on the applied voltage.

Full text of DOI:10.1039/c8cc00494c

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Electrochemically driven host-guest interactions on patterned
donor/acceptor self-assembled monolayers
Maria Serena Maglione, a Javier Casado-Montenegro, a Eva-Corinna Fritz, b Núria Crivillers, a Bart
Jan Ravoo, b Concepció Rovira, a Marta Mas-Torrent a*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
Here, on Au//ITO patterned substrates SAMs of ferrocene (Fc) on the surface properties, here, on Au//ITO patterned substrates SAMs
the Au regions and of anthraquinone (AQ) on the ITO areas are of ferrocene (Fc) as electron donor on the Au regions and of
prepared exhibiting three stable redox states. Further, by anthraquinone (AQ) as an electron acceptor on the ITO areas were
selectively oxidizing or reducing the Fc or AQ units, respectively, prepared. Hence, by selectively oxidizing or reducing the Fc or AQ
the surface properties are locally modified. As a proof-of-concept, units, respectively, the surface properties were locally modified. As
such confinement of the properties is exploited to form locally a proof-of-concept, we demonstrate that such confinement of the
host-guest complexes with β-cyclodextrin on specific surface properties can be exploited to form locally host-guest complexes
regions depending on the applied voltage.
with β-cyclodextrin (β-CD) on specific surface regions depending on
the applied voltage, since only the more hydrophobic redox forms
The surface modification of solid inorganic supports with chemically of AQ and Fc form stable complexes.
bonded self-assembled monolayers (SAMs) has been proved to be a For the fabrication of
electroactive
SAMs,
11-
promising and versatile route to modify the chemical or physical (ferroceny)lundecanethiol (FcSH) and the anthraquinone derivative
properties of a substrate.1-4 Additional interest is focused on the 9,10-dioxo-N-(3-(triethoxysilyl)propyl)-9,10-dihydroanthracene-2-
development of smart surfaces that are able to respond to an carboxamide (AQSi) were selected (Figure 1a). It is well-known that
external stimulus since they represent potential platforms for Fc undergoes one reversible oxidation process (Fc-e-⇌Fc+)32 and
sensing and transmitting information about the physical, chemical that AQ, in protic media, exhibits a two-proton, two-electron
and/or biological changes produced in our environment.5-9 In this reduction process forming the corresponding anthrahydroquinone
context, SAMs of electroactive molecules on conductive surfaces (AQ+2e-+2H+⇌AQH2).33-35 FcSH has a thiol as anchoring group for
(e.g. gold, indium-tin oxide (ITO), etc.) offer the opportunity to tune grafting to gold, while AQSi, which has been synthetized as
the surface properties by the application of an electrical signal.10-19
Triggering the SAM redox state can result in remarkable alterations
of the surface optical, magnetic or chemical properties.20-24 For
instance, following this strategy, the surface wettability has been
importantly tuned employing SAMs of electron donor (D) or
electron acceptor (A) molecules.25-28 This is particularly appealing in
the field of bio-sensing since such changes can be exploited to
modify the affinity to the surface of hydrophilic bio-molecules.29, 30
In order to further progress in this field, it is highly desirable to
achieve a local control and addressability of the surface properties.
Previously, we reported the preparation of mixed D/A bi-
component SAMs on Au to realize surfaces exhibiting multiple
accessible redox states by the application of the appropriate bias
voltage.31 In order to go a step further and achieve a local control of
Figure 1. a) Molecular structure of the molecules used. Redox processes of Fc (b)
and AQ in a protic media (c). d) Schematic representation of AQSi//FcSHdil
patterned SAM and its ternary switch as a result of the oxidation of ferrocene
and the reduction of anthraquinone. For clarity, the alkanethiols present in the
diluted FcSHdil-SAM have been omitted.
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reported in literature,36 bears a triethoxysilane able to react with
ITO. Initially SAMs of each electroactive species were prepared and
characterised by cyclic voltammetry (CV), water contact angle (CA)
and X-ray photoelectron spectroscopy (XPS) (see ESI). SAMs of Fc on
gold were prepared diluted with 1-decanethiol (C10SH) in a ratio 1:9
(FcSH:C10SH) as previously reported, namely FcSHdil-SAM, to avoid a
highly dense Fc layer which would prevent the formation of
supramolecular interactions with cyclodextrin.37 The CA of these
FcSHdil-SAMs was found to be 103.7± 1.1º, which is higher than the
value obtained for undiluted SAMs (78± 3.4º) in agreement with the
more hydrophobic character of alkanethiol.38 The CV of this SAM
was
performed using
a
conventional three-electrode
electrochemical setup with the modified gold substrate used as the
working electrode, a platinum wire as counter electrode and a silver
wire as quasi-reference (Figure S2, ESI). A phosphate buffer solution
Figure 2. CV of AQSi//FcSHdil patterned SAM. The modified ITO//Au patterned
substrate is used as the working electrode vs Ag(s) and a Pt wire is used as the
counter electrode in a phosphate buffer solution pH ̴ 6.9. For clarity, the
alkanethiols present in the diluted FcSHdil-SAM have been omitted.
at pH ̴ 6.9 was employed as electrolyte. The oxidation peak of the
system is observed at E1/2=+0.26 V and the surface coverage was
estimated to be 1.2 x 10-10 mol/cm2 (see ESI). This value is in
agreement with values reported in the literature for similarly
diluted Fc SAMs.37
In order to demonstrate that the surface properties can be
locally modified by an electrical signal, we took advantage of the
fact that both AQ and Fc can form host-guest complexes with β-
cyclodextrin (β-CD) in solution as well as when they are anchored
on substrates, with binding affinities in the range of 2-5 × 104 M-1
and 1-3× 103 M-1 for Fc and AQ moiety, respectively.40-46. It should
be noted that supramolecular chemistry and, particularly, host-
guest interactions, are promising tools in biological as well as
materials applications due to the dynamic nature of non covalent
interactions and, in addition, because the incorporation of guests
can be controlled using external stimuli.47,48 In the present case, the
complexes formation of [β-CD][Fc] and [β-CD][AQ] is disfavoured
when the Fc is in its oxidized state or the AQ in its reduced state,
respectively, due to their higher hydrophilic character that hampers
the electroactive unit from entering into the more hydrophobic CD
cavity.49,50 Hence, by applying a controlled electrical stimulus the
formation of a host-guest complex could be in principle controlled
along the surface.
SAMs of AQSi were prepared on freshly activated ITO substrates
(see procedure in the Experimental Section). The electrochemical
characterization of AQSi-SAM on ITO (Figure S3, ESI) was carried
out in the same conditions described above for the SAM of
ferrocene. The CV exhibited a redox peak corresponding to the
reduction of the anthraquinone at E1/2= -0.64 V. The SAM formation
was studied by monitoring the CV response after 2, 4, 8 and 48
hours of immersion of the ITO surface in the AQSi solution. By
analyzing the surface coverage, it was observed that after 4 hours
of immersion a coverage of 1.6 x 10-10 mol/cm2 was reached, and
further immersion times did not improve significantly this value
(Figure S4, ESI). The minimization of the immersion time is crucial
for the subsequent preparation optimization of the patterned
AQSi//FcSHdil SAMs where two steps are required (see below).
Importantly, the coverage of AQSi-SAM is of the same order as the
one of the FcSHdil-SAMs. Hence, if the AQ units are homogenously
distributed, the SAM should be suitable for the complex formation
with CD. The CA of the AQSi-SAM was 61.1±1.5º.
As a first step, we monitored the formation of the host-guest
complexes of β-CD with the Fc and AQ SAMs in real time by surface
plasmon resonance (SPR), where the SPR response is measured as
refractive index unit (RIU). For these experiments it is required to
work on plasmonic Au surfaces, which were immersed in diluted
solutions of the SAM precursor FcSH and a solution of the
Patterned surfaces with ITO//Au regions were prepared by gold
evaporation on the ITO-coated glass substrate using a metallic
mask. The surface functionalisation with AQSi and Fc was carried
out in two steps. Firstly, the freshly cleaned and activated substrate
was immersed in a millimolar solution of AQSi in toluene during 4 h,
under inert conditions, to functionalise the ITO coated regions.
Then, the substrates were rinsed with toluene to eliminate the
physisorbed molecules, dried under a nitrogen flow and immersed
overnight in the second millimolar solution of FcSH:C10SH 1:9 in
ethanol to functionalise the gold surface. Finally, the substrate was
rinsed with ethanol and dried with nitrogen. It is important to
highlight here that the functionalisation of ITO had to be realized
first since the surface oxide has to be activated in an ozone cleaner
chamber to promote the formation of reactive hydroxyl groups
immediately previous to the surface functionalisation.39 The
resulting AQSi//FcSH SAM was characterized by CV. As expected,
two redox processes corresponding to the oxidation of Fc and
reduction of AQ were observed, giving rise to a ternary switch:
AQH2//Fc ⇌AQ//Fc ⇌AQ//Fc+ (Figure 1d, Figure 2).
Figure 3. Sensorgrams (i.e., variation of refractive index unit with time) of the
controlled formation and disaggregation of the host-guest complexes between
β-CD and a) AQS2-SAM and b) FcSHdil-SAM on Au surfaces. Flow rate: 100 µL/min.
Injections: β-CD = black arrows, Na2S2O4 = green arrows, FeCl3 = red arrows.
Continuous arrows indicate when the reagent reaches the surface and
discontinuous when is removed.
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31
anthraquinone disulfide AQS2. (Figure 1a) The disulfide can also
bind to gold by forming a thiolate gold bond and thus, can be
regarded as an analogue system of AQSi-SAM on ITO. The detected
SPR curves are shown in Figure 3. In Figure 3a, the SPR response of
the AQS2-SAM is observed to increase to 4 mRIU during the addition
of a solution of 1 mM β-CD in milliQ water of 18 minutes.
Afterwards the surface is rinsed with milliQ water to remove
unbound β-CD. As a result the SPR response decreases at 1.3 mRIU,
indicating the formation of the host-guest complex. However, upon
addition of a reducing agent (i.e., 2 mM Na2S2O4) from t = 55-73
min, the signal first increases due to the change in the refractive
index of the reducing agent compared to pure milliQ water.
However, from t = 73 min onwards the SPR response decreases due
to the release of β-CD resulting from the formation of the reduced
species AQH2S2. As a control experiment, β-CD was injected again at
t =135 min resulting in a steady SPR signal after rinsing with milliQ
water (t = 155 min), which confirms that in this redox state the
complex is not formed.
In the case of the FcSHdil-SAM a comparable experiment was
performed (Figure 3b). Upon addition of a 1mM solution of β-CD in
milliQ water from t = 2-6 min to the functionalized surface a notable
change of mRIU was observed, which becomes stable after rinsing
with milliQ water at 1 mRIU indicating the formation of the [β-
CD][Fc] complex. Subsequently, a 1 mM solution of FeCl3 was added
during t = 13-15 min to oxidize the electroactive Fc units and to
disaggregate the complex. To proof the presence of the oxidized Fc
and the inactivity towards a host-guest complexation with β-CD, the
host molecule was injected again at t = 40 min. The addition of β-
CDs did not induce any increase of the SPR response after rinsing
with milliQ water demonstrating the on-off switching of the
formation of the host-guest complex.
Figure
4
.
a) Schematic representation of the electrochemically targeted
interaction between F-β-CD and FcSH on gold and AQSi on ITO. b) Confocal
images of the substrate AQSi//Fc+SHdil on the left and AQH2Si//FcSHdil on the
right after promoting the selective interaction with F-β-CD. c) Plot of the
fluorescence intensity along the surface. For clarity, the alkanethiols present in
the diluted FcSHdil-SAM have been omitted in the scheme.
steric hindrance.
The last step to achieve the final goal was to prove the
controlled trapping of β-CD on a specific location depending on the
voltage applied on the substrates patterned with AQSi//FcSHdil
SAMs. For this propose, fluoresceine functionalized β-cyclodextrins
(F-β-CD) (Figure S9, ESI) was used as analyte in order to be able to
visualise the formation of the supramolecular complexes by
confocal microscopy (Figure S10, ESI). The patterned substrates
were immersed in an electrochemical cell filled with a phosphate
To further corroborate the formation of the host-guest
complexes CA, CV and XPS experiments were performed. Gold
substrates functionalized with FcSHdil-SAM and ITO substrates with
AQSi-SAMs were immersed in a 9 mM solution of β-CD in milliQ
water for 3 h. Afterwards the substrates were rinsed and dried. The
resulting substrates exhibited a change in the CA values from
103.7± 1.1º to 84±1.5º, in the case of FcSHdil-SAM, and from 61.1 ±
1.5º to 39.9 ± 2.1º, in the case of AQSi-SAM. That is, the substrates
are more hydrophilic upon the complex formation in accordance
with the hydrophilic character of the β-CD exterior part. CV
measurements were also performed before and after the
complexes formation. It is assumed that the Fc and the AQ units
once they are in the β-CD cavity are not electroactive any more.41-51
Thus, as it is observed in Figure S5 and Figure S6 from ESI, the
current intensity of the CV peaks decrease for both functionalized
buffer solution at pH ̴ 6.9 containing 60% (m/v) of F-β-CD and used
as working electrodes in the following chronoamperometry
experiments. Then, a constant potential of +0.6 V vs Ag(s) was
applied for 5 min to oxidize the Fc units, so then the F-β-CDs in the
electrolyte medium could only interact with AQ moieties located on
the ITO stripes (Figure 4a). Alternatively, a potential of -0.8 V vs
Ag(s) was applied for 5 min to reduce the AQ units and promote the
formation of the host-guest complex only between F-β-CDs and the
Fc units present on the Au coated regions (Figure 4a). All these
experiments were examined by confocal microscopy (Figure 4b-c).
Clearly, it was observed that depending on the applied voltage the
fluorescence derived from F-β-CDs could only be seen on the ITO or
Au areas, confirming that the host-guest supramolecular
interactions can be electrochemically steered and locally addressed.
In summary, we employed ITO//Au patterned surfaces to
confine electroactive molecules with specific anchoring groups on
defined surface regions. In particular, we prepared substrates
exhibiting three stable redox states based on segregated SAMs of
donor (i.e., Fc) and acceptor (i.e., AQ) molecules. Further, we
showed that the electroactive units anchored on the substrate form
host-guest complexes with β-CD via supramolecular interactions
substrates after complexation.52 Finally, in the XPS of the FcSHdil
-
SAM, the complex formation is proved by the appearance of new
peaks at binding energies around 286 and 288 eV for the C1s and
533 eV for the O1s coming from the β-CD (Figure S7, ESI). In the
AQSi-SAM, the news peaks around 286 and 533 eV confirms the
presence of β-CD on the surface (Figure S8,
ESI). Considering all above, it can be firmly stated that both FcSHdil
-
SAM and AQSi-SAM can form complexes with β-CD. It should be
also mentioned that diluting the AQSi-SAM was not beneficial for
improving the complexation efficiently, while non diluted Fc SAMs
were not optimal for forming complexes with β-CD due to a high
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reduced such interactions are no longer favoured. Hence, by
applying the appropriate electrical signal the formation of the host-
guest complex and hence, the trapping of the β-CD, has been locally
guided on the surface. This work represents a proof-of-concept of
how by an appropriate interface engineering the surface properties
can be locally tuned, which could be of interest in a variety of
disciplines such as in the field of sensors or for bio-applications.
This work was funded by ERC StG 2012-306826 e-GAMES, ITN
iSwitch 642196, Networking Research Center on Bioengineering,
Biomaterials, and Nanomedicine (CIBER-BBN), the DGI (Spain)
project FANCY CTQ2016-80030-R, the Generalitat de Catalunya
(2014-SGR-17) and the Spanish Ministry of Economy and
Competitiveness, through the “Severo Ochoa” Programme for
Centers of Excellence in R&D (SEV-2015-0496). M. S. M. is enrolled
in the Materials Science PhD Program of Universitat Autònoma de
Barcelona.
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