Step-by-Step Layer-by-Layer Assembly Using 1,2,3-Triazole as a Platform for Controlled Multicharged and Multifunctional Coatings

Article abstract of DOI:10.1002/cplu.201500214

Reported for the first time is the use of click chemistry to make layer-by-layer multiple post-functionalization treatments. The use of triazole as a platform for the post-functionalization allows the introduction of new clickable structures on the surface. The layer-by-layer strategy by means of click chemistry allows the introduction of both multiple and/or different consecutive modifications on the surface and multicharged species. Herein it consists of the use of molecules functionalized by a 1-azido group and propargyl bromide to deposit functionalized triazolium-type charged oligomers on the substrate. Moreover, different functional groups can be introduced at each step, which amplifies the use of this strategy for many potential applications. Here, to give an example of applications, that strategy is used to introduce alkyl chains and obtain highly hydrophobic materials. Moreover, it is shown that the surface morphology can also change after each treatment.

Full text of DOI:10.1002/cplu.201500214

DOI: 10.1002/cplu.201500214
Full Papers
Step-by-Step Layer-by-Layer Assembly Using 1,2,3-Triazole
as a Platform for Controlled Multicharged and
Multifunctional Coatings
Guilhem Godeau, Thierry Darmanin, and FrØdØric Guittard*[a]
Reported for the first time is the use of click chemistry to
make layer-by-layer multiple post-functionalization treatments.
The use of triazole as a platform for the post-functionalization
allows the introduction of new clickable structures on the sur-
face. The layer-by-layer strategy by means of click chemistry
allows the introduction of both multiple and/or different con-
secutive modifications on the surface and multicharged spe-
cies. Herein it consists of the use of molecules functionalized
by a 1-azido group and propargyl bromide to deposit function-
alized triazolium-type charged oligomers on the substrate.
Moreover, different functional groups can be introduced at
each step, which amplifies the use of this strategy for many
potential applications. Here, to give an example of applica-
tions, that strategy is used to introduce alkyl chains and obtain
highly hydrophobic materials. Moreover, it is shown that the
surface morphology can also change after each treatment.
Introduction
Functional substrates cover a wide range of interest.[1–4] The
fields of applications are varied and include industrial, smart
materials, biomedical applications as well as wettability appli-
cations. Depending on the research field, the substrate needs
to be controlled in both function and morphology. Various
ways have been described for functional substrate prepara-
tion,[5] among them, post-functionalization has recently
become a particular area of interest.[6] This strategy allows vari-
ous properties to be given to one unique synthesized surface.
Usually, the surface morphology depends on the surface prep-
aration and the function on the post-functionalization. Functio-
nalizable surfaces can be prepared by means of various path-
ways, including chemical or physical modifications. Various
strategies can be used to obtain structured surfaces. Among
them, electrochemical polymerization allows fine-tuning of the
surface morphology by altering the monomer structure and
electrochemical parameters, thereby making the electrodeposi-
tion of conductive polymer a choice method.[7] Thanks to their
specific electrochemical properties (high conductivity, easily
and quickly polymerizable), the 3,4-ethylenedioxythiophene
(EDOT)-derived monomers are key molecules for the electropo-
lymerization.[8,9] Moreover, the electropolymerization also
allows the introduction of functional groups such as azido
groups, which can be used for post-functionalization treat-
ments.[10–13]
cially the Sharpless-modified Huisgen reaction, used for click
chemistry, was studied extensively.[16,17] The 1,3-dipolar cycload-
dition is a well-known reaction between an azido group and
an alkyne and allows two structures to covalently link and
form a triazole group. That efficient and orthogonal chemical
pathway allows the easy introduction of one modification. Vari-
ous pathways are described to introduce a secondary group
on the triazole.[18] Among them, layer-by-layer post-functionali-
zation using a polymer-bearing azido group or alkyne are of in-
terest.[19,20] The first polymer (N3) reacts on the surface and the
second polymer (alkyne) can react on the remaining unreacted
azido group; the unreacted alkyne groups are then engaged in
a new round of click reaction, and so forth. That strategy
allows the development of a multilayer surface but lacks selec-
tivity. All unreacted structures from all layers can be engaged.
A nice option to make the click reaction selective is to distin-
guish between the alkyne reactivity by using protecting
groups. This strategy was described by Carell’s group to intro-
duce multiple functions on biomacromolecules by using click–
click–click chemistry.[21] That step-by-step approach, in which
the second reaction occurs only after deprotection of the
second reactive alkyne, is key for multiple and selective func-
tionalization.
Herein, we report for the first time, the use of the Huisgen
reaction for step-by-step layer-by-layer multiple post-function-
alization treatment (Scheme 3). We also used another feature
of triazoles to add a function. Triazole possesses a free elec-
tronic doublet not engaged in the aromatic ring;[10] this dou-
blet is suitable for attacking halogenated molecules and forms
substituted triazolium halides.
In the last decade, the post-functionalization of macromole-
cules, macrobiomolecules as well as substrates has been well
studied.[14,15] Various chemical pathways to functionalization
were described. Among them, the Huisgen reaction and espe-
[a] Dr. G. Godeau, Dr. T. Darmanin, Prof. F. Guittard
UniversitØ Nice Sophia Antipolis
CNRS, LPMC, UMR 7336
The key point of our strategy is the use of propargyl bro-
mide as a halogenated molecule to introduce a new function
suitable for a click reaction (Figure 1, reaction i). Interestingly,
each step of the click reaction provides a new triazole suitable
06100 Nice (France)
E-mail: guittard@unice.fr
ChemPlusChem 2015, 80, 1691 – 1695
1691
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Full Papers
Figure 1. General procedure for step-by-step layer-by-layer post-functionalization: (i) propargyl bromide, toluene, RT overnight; (ii) 1-azidododecane, copper
sulfate, sodium ascorbate, THF/water (50:50), RT 3 h.
for modification (Figure 1, reaction ii) and allows subsequent
layer-by-layer post-functionalization. To observe a significant
impact on surface properties, we focus in this study on the ad-
dition of long alkyl hydrophobic chains using alkyl azides.
Indeed, the alkyl chains are more hydrophobic than triazolium
groups.
Results and Discussion
Scheme 1. General procedure for the preparation of the PEDOT click surface:
(i) 3,4-dimethoxythiophene (0.5 equiv), 1,2,6-hexanetriol (1 equiv), para-tolu-
Synthesis of the monomers
enesulfonic acid (0.05 eq), toluene, reflux 36 h; (ii) methanesulfonyl chloride
In this study, the first step was the elaboration of a structured
(1.5 equiv), triethylamine (3 equiv), dichloromethane, RT, 4 h; (iii) sodium
azide (5 equiv), acetone, reflux overnight; (iv) electropolymerization; (v) oct-
surface suitable for the Huisgen reaction. To prepare such
a kind of surface, a monomer-bearing azido group was first
synthesized (Scheme 1).
1-yne, copper sulfate, sodium ascorbate, THF/H2O (50:50), RT 3 h.
Because of the possible steric hindrance in the multiple
click-chemistry steps and to aid the electrodeposition, a butyl
spacer was introduced between the EDOT moiety and the
azido group. The starting monomer was synthesized in
a three-step synthesis starting with 3,4-dimethoxythiophene
(Scheme 2). The first step is a reaction between 3,4-dimethoxy-
thiophene and 1,2,6-hexanetriol. That step was catalyzed by
para-toluenesulfonic acid and was carried out in toluene
(reflux) over 36 hours. The target (4-hydroxybutyl)EDOT
(EDOT–OH) was obtained in 51% yield. The next step was a re-
action between EDOT–OH and methanesulfonyl chloride
(MsCl). That reaction took place
Scheme 2. Synthetic pathway to EDOT–N3.
one night at reflux, (4-azidobutyl)–EDOT (EDOT–N3) was ob-
tained with 75% yield.
in dichloromethane with triethyl-
amine. When the reaction was
finished, all the volatiles were re-
moved and the formed yellowish
oil could be used for the next
step without any purification.
For the final step, the yellowish
oil was dissolved in acetone and
sodium azide was added. After Scheme 3. General concept for multiple layer-by-layer post-functionalization.
ChemPlusChem 2015, 80, 1691 – 1695
www.chempluschem.org
1692
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Full Papers
The formed EDOT–N3 is suitable for electropolymerization.
To obtain highly homogeneous and adherent films, cyclic vol-
tammetry was chosen as the electrodeposition method. First,
the monomer oxidation potential was determined. That poten-
tial was measured at 1.43 V versus a saturated calomel elec-
trode (SCE). Then, the monomer was dissolved in 0.1m tetra-
butylammonium perchlorate in anhydrous acetonitrile (CH3CN)
and deposited on a gold-covered wafer as working electrode.
The electrodepositions were performed from À1.00 to 1.37 V
at a scan rate of 20 mVsÀ1 and using a different number of
deposition scans (1, 3, and 5). The cyclic voltammogram after
five deposition scans in given in Figure 2.
Figure 3. A) Apparent contact angle with water for modified surfaces; SEM
images for B) PEDOT–N3, C) triazole 0, D) Click 1, E) Click 2, and F) Click 3.
Scale bars: 1 mm.
that contact angle fell to 878 (slightly hydrophilic). This result is
clearly relevant for triazolium salt formation. The second round
of click reaction gave PEDOT–Click 1 with qw =1268. PEDOT–
Click 1 can be described as hydrophobic. That contact angle is
a little lower than the one from PEDOT–Triazole 0. For the next
steps, PEDOT–Triazolium 2 and 3 have qw values of 74 and 728,
respectively, and can be clearly described as hydrophilic, which
is consistent with the triazolium properties. The third round of
click reaction formed PEDOT–Click 2, the surface of which
showed properties close to that of PEDOT–Click 1 with qw =
1248. The fourth round of click reaction showed significantly
different results with qw =828. That final surface cannot be de-
scribed as hydrophobic but is still significantly different from
the starting PEDOT–triazolium 3, which allowed us to confirm
the modification. To give better explanations for these results,
the surface morphologies were observed to evaluate the sur-
face morphology changes after each treatment.
Figure 2. Cyclic voltammogram from EDOT–N3 to PEDOT–N3 (0.01m) on
gold plate recorded in 0.1m tetrabutylammonium perchlorate/CH3CN.
The electrodeposited conducting polymer PEDOT–N3 was
then post-modified by using the Sharpless-modified Huisgen
reaction (Scheme 1, step v).[16] PEDOT–N3 was modified using
commercially available octyne with copper sulfate and sodium
ascorbate in a mixture of water/THF (50:50). That first round of
click reaction gave the PEDOT–Triazole 0 (Figure 1). Triazole ex-
hibits an electronic doublet that is not engaged in the aromat-
ic ring. That doublet makes the triazole a platform for further
modification. The triazole was treated with propargyl bromide
to introduce a new clickable function as a propargyl triazolium
bromide (PEDOT–Triazolium 1). The formed propargyl triazoli-
um bromide can then be engaged in a new click reaction with
an azido group. In this study, the chosen azido alkyl chain was
1-azidododecane. The second click reaction was performed be-
tween the triazolium surface and 1-azidododecane in a THF/
water mixture with copper sulfate and sodium ascorbate and
gave PEDOT–Click 1. The newly formed second-generation tria-
zole was also able to form a new propargyl triazolium bromide
(PEDOT–Triazolium 2). That cycle can be performed at least
three times after the first click reaction (until PEDOT–Click 3).
This strategy allows the introduction of four consecutive func-
tionalizations on the substrate.
Scanning electronic microscopy images for PEDOT–N3, tria-
zole 0, and Click 1, 2, and 3 are given in Figure 3B–F, respec-
tively. The starting PEDOT–N3 has a structured fibrillar morphol-
ogy (Figure 3B). After the first click reaction, the triazolium 0
(Figure 3C) formed rougher fibrillar structures. The highly struc-
tured surface is consistent with the hydrophobic properties of
the surface.
After the second round of modification (PEDOT–Click 1), the
surface evolves but still shows a nicely defined fibrillar mor-
phology (Figure 3D). The next round of click modification
(PEDOT–Click 2) gives more aggregated surfaces. The morphol-
ogy appears to be more broad but still has a fibrillar basis (Fig-
ure 3E); this fibrillar structure is consistent with the hydropho-
bic properties. Some microclusters are also present on this sur-
face. In the final step (PEDOT–Click 3), a huge change in the
surface morphology was observed (Figure 3F). Here, a change
from fibrillar structures to microclusters was clearly demon-
strated, which also explains the large decrease in qw. We think
that the surface morphology is affected after the click reaction
because we start with polymer films (PEDOT–N3) that have
a nanofibrous morphology. Indeed, it is known that polymer
nanofibers are highly sensitive nanostructures owing to their
flexibility and low capillary forces. As a consequence, they can
collapse or coalesce, for example.[22–26] This is in agreement
Owing to changes in the properties on going from triazole
to triazolium and after functionalization by alkyl groups, the
surface functionalization was followed by measuring the water
apparent contact angle (qw) (Figure 3A). After the first click re-
action and the introduction of an alkyl chain, qw for PEDOT–Tri-
azole 0 was close to 1378 and can be clearly described as hy-
drophobic. After immersion in propargyl bromide overnight,
ChemPlusChem 2015, 80, 1691 – 1695
www.chempluschem.org
1693
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Full Papers
CDCl3): d=142.0, 141.6, 99.3, 73.6, 68.4, 62.6, 32.4, 30.4, 21.3 ppm;
EI-MS: m/z=213.9.
with another study showing the influence of the surface struc-
tures using alkynes of various lengths.[27] The formation of the
nanoclusters can also be explained by the presence of the
multicharged triazolium-type oligomers.
EDOT–N3: EDOT–OH (1.9 g, 8.9 mmol) was dissolved in dichloro-
methane (50 mL). Triethylamine (1.8 g, 2 equiv, 17.8 mmol) was
added and the mixture was cooled to 08C. Methanesulfonyl chlo-
ride (1.2 g, 1.2 equiv, 10.6 mmol) was added dropwise. The mixture
was allowed to warm up at room temperature. After 4 h, methanol
(10 mL) was added. The mixture was stirred for an additional
30 min. All volatiles were removed under reduced pressure. The re-
sidual oil was dissolved in acetone (100 mL) and NaN3 (2.9 g,
5 equiv, 44.5 mmol) was added. The mixture was heated at reflux
overnight. The reaction was then allowed to cool at room tempera-
ture and most of the acetone was removed under reduced pres-
sure. Dichloromethane (100 mL) was then added. The organic layer
was washed two times with water (30 mL) and once with brine
(30 mL). The organic layer was dried with MgSO4 and filtered. The
solvents were removed under reduced pressure. EDOT–N3 was fi-
nally purified on a column (95:5 cyclohexane/ethyl acetate). Yield:
colorless oil (1.6 g, 75%); Rf =0.66 (8:2, cyclohexane/ethyl acetate).
1H NMR (200 MHz, CDCl3): d=6.3 (s, 2H), 4.11–4.18 (m, 2H), 3.85–
3.92 (m, 1H), 3.28–3.35 (m, 2H), 1.56–1.66 ppm (m, 8H); 13C NMR
(200 MHz, CDCl3): d=141.9, 141.6, 99.4, 73.4, 68.3, 51.2, 30.1, 28.7,
22.3 ppm; EI-MS: m/z=239.9.
Conclusion
In this study, we reported for the first time the use of the Huis-
gen reaction to make layer-by-layer multiple post-functionali-
zation treatments on a substrate. We observed the multiple
modifications using alkyne and propargyl bromide by follow-
ing the wettability properties of the surfaces and confirmed
the possibility to introduce multiple surface modifications. We
also showed a decrease in qw after each cycle, which is due to
a change in the surface morphology from nanofibrillar struc-
tures to microclusters. The presence of nanoclusters is proba-
bly due to the formation of multicharged triazolium-type oligo-
mers. This strategy could be used in the close future to add
different functional structures to provide specific properties
(biocide, anti-adherent, superoleophobicity, etc.) to the surface.
The counterions of the triazolium groups could also be used
to introduce modifications to the surface wettability (smart
materials) or to introduce other functions.[28]
1-Azidododecane: 1-Bromododecane (2 g, 20 mmol) was dissolved
in acetone (100 mL) and NaN3 (6.5 g, 5 equiv, 100 mmol) was
added. The mixture was heated at reflux overnight. The reaction
was then allowed to cool at room temperature and most of the
acetone was removed under reduced pressure. Dichloromethane
(100 mL) was then added. The organic layer was washed two times
with water (30 mL) and once with brine (30 mL). The organic layer
was dried with MgSO4 and filtered. That reaction gave 1-azidodo-
decane (3.6 g) as a colorless oil (yield: 85%). This compound was
used for the next step without further purification. All spectroscop-
ic data agreed with the literature.[29]
Experimental Section
Measurements
NMR spectra were performed with a Bruker W-200 MHz spectrome-
ter. Electrochemical experiments were performed with an Autolab
PG STAT 30 potentiostat from Eco Chemie B. V. equipped with Gen-
eral Purpose Electrochemical System (GPES) software. A three-elec-
trode cell, equipped with either a platinum disk (area=7.1 mm2) or
a gold plate (area=1.5 cm2) as working electrode, a glassy carbon
rod as counter electrode, and a SCE reference electrode, was used.
For each experiment, an anhydrous acetonitrile solution containing
0.01m of the monomer and 0.1m tetrabutylammonium perchlorate
(Bu4NClO4) was used. The solutions were degassed with argon
before each experiment. Contact-angle measurements were per-
formed with a Krüss DSA-30 contact-angle goniometer at (21Æ
1)8C. An average of three measurements with water (gL =
72.8 mNmÀ1) was made to determine the hydrophobicity of the
surfaces. Scanning electron microscopy images were performed
with a JEOL 6700F microscope.
Electrodeposition
0.01m EDOT–N3 was inserted into a glass cell containing 0.1m tet-
rabutylammonium perchlorate (Bu4NClO4) dissolved in dry acetoni-
trile. Three electrodes were put inside the solution. Gold plates
(purchased from Neyco), glassy carbon rods, and a saturated calo-
mel electrode (SCE) were used as the working, counter, and refer-
ence electrodes, respectively. The three electrodes were connected
to an Autolab potentiostat (Metrohm). Before each experiment, the
solution was degassed with argon. The depositions were per-
formed by using cyclic voltammetry from À1.00 to 1.37 V at a scan
rate of 20 mVsÀ1 and using different deposition scans (1, 3, and 5).
After the deposition, the PEDOT–N3 samples were cleaned three
times with acetonitrile to remove the remaining salts.
Synthesis
EDOT–OH: 2,3-Dimethoxythiophene (2.5 g, 17.3 mmol) was dis-
solved in toluene (100 mL). Hexan-1,2,6-triol (4.6 g, 34.6 mmol) and
para-toluenesulfonic acid monohydrate (665 mg, 3.5 mmol) were
then added. The mixture was warmed at 110 8C over 36 h. The mix-
ture was then allowed to cool at room temperature. The organic
phase was extracted twice with 5% aqueous NaHCO3 (2”30 mL)
and was then washed with brine (30 mL). The organic layer was
then dried with MgSO4. After filtration, the solvent was removed
under reduced pressure. The compound was finally purified on
a column (8:2 cyclohexane/ethyl acetate). Yield: Slightly yellow oil
(1.9 g, 51%); Rf =0.5 (5:5 cyclohexane/ethyl acetate); 1H NMR
(200 MHz, CDCl3): d=6.3 (s, 2H), 4.1–4.18 (m, 2H), 3.85–3.91 (m,
1H), 3.64–3.71 (m, 2H), 1.52–1.69 ppm (m, 8H); 13C NMR (200 MHz,
Click on PEDOT–N3
The surface of PEDOT–N3 was immersed in a 50:50 water/THF solu-
tion (5 mL). CuSO4 (100 mg, 0.6 mmol), sodium ascorbate (100 mg,
0.1 mmol), and octyne (100 mg, 0.9 mmol) were then added. The
mixture was shaken for 3 h. The polymer was then successively
washed 3 times with water and 3 times with ethanol. The polymer
was then dried.
ChemPlusChem 2015, 80, 1691 – 1695
www.chempluschem.org
1694
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Full Papers
[9] T. Darmanin, F. Guittard, Adv. Mater. Interfaces 2015, 2, DOI: 10.1002/
admi.201500081.
Triazolium formation
The surface of PEDOT–triazole was immersed in a 80% propargyl
bromide–toluene solution (5 mL). The mixture was shaken over-
night. The polymer was then successively washed 3 times with
water and 3 times with ethanol and dried.
[10] H.-B. Bu, G. Goetz, E. Reinold, A. Vogt, S. Schmid, R. Blanco, J. L. Segura,
P. Baeuerle, Chem. Commun. 2008, 1320–1322.
[11] H.-B. Bu, G. Goetz, E. Reinold, A. Vogt, R. Azumi, J. L. Segura, P. Baeuerle,
Chem. Commun. 2012, 48, 2677–2679.
[12] J. Sinha, R. Sahoo, A. Kumar, Macromolecules 2009, 42, 2015–2022.
[13] E. Scavetta, R. Mazzoni, F. Mariani, R. G. Margutta, A. Bonfiglio, M. Deme-
las, S. Fiorilli, M. Marzocchi, B. Fraboni, J. Mater. Chem. B 2014, 2, 2861–
2867.
Click on propargyl triazolium
[14] T. Michinobu, Chem. Soc. Rev. 2011, 40, 2306–2316.
[15] G. Godeau, H. Arnion, C. Brun, C. Staedel, P. Barthelemy, Med. Chem.
Commun. 2010, 1, 76–78.
[16] R. Huisgen, 1,3-Dipolar Cycloaddition Chemistry, Wiley, New York, 1984,
p. 1–176.
The surface of PEDOT–triazolium was immersed in a 50:50 water/
THF solution (5 mL). CuSO4 (100 mg, 0.6 mmol), sodium ascorbate
(100 mg, 0.1 mmol), and 1-azidodecane (100 mg, 0.55 mmol) were
then added. The mixture was shaken for 3 h. The polymer was
then successively washed 3 times with water and 3 times with eth-
anol and dried.
[17] C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057–
3064.
[18] L. Li, G. Zhang, A. Zhu, L. Zhang, J. Org. Chem. 2008, 73, 3630–3633.
[19] W. J. Yang, D. Pranantyo, K.-G. Neoh, E.-T. Kang, S. L.-M. Teo, D. Rittschof,
Biomacromolecules 2012, 13, 2769–2780.
Acknowledgements
[20] Y. Zhang, H. He, C. Gao, J. Wu, Langmuir 2009, 25, 5814–5824.
[21] P. M. E. Gramlich, S. Warncke, J. Gierlich, T. Carell, Angew. Chem. Int. Ed.
2008, 47, 3442–3444; Angew. Chem. 2008, 120, 3491–3493.
[22] D. Chandra, S. Yang, Acc. Chem. Res. 2010, 43, 1080–1091.
[23] A. Grinthal, S. H. Kang, A. K. Epstein, M. Aizenberg, M. Khan, J. Aizen-
berg, Nano Today 2012, 7, 35–52.
We thank J. P. Laugier and CCMA (Centre Commun de Microsco-
pie AppliquØe) Univ. Nice Sophia Antipolis for recording the SEM
images.
[24] X.-F. Wu, Y. A. Dzenis, Nanotechnology 2007, 18, 285702/1–285702/6.
[25] T. S. Kustandi, V. D. Samper, D. K. Yi, W. S. Ng, P. Neuzil, W. Sun, Adv.
Funct. Mater. 2007, 17, 2211–2218.
Keywords: click chemistry · cycloaddition · electrochemistry ·
post-functionalization · surface chemistry
[26] A. J. Guenthner, S. Khombhongse, W. Liu, P. Dayal, D. H. Reneker, T. Kyu,
Macromol. Theory Simul. 2006, 15, 87–93.
[27] G. Godeau, J. N’Na, T. Darmanin, F. Guittard, J. Phys. Chem. B 2015, 119,
6873–6877.
[28] M. Doebbelin, R. Tena-Zaera, R. Marcilla, J. Iturri, S. Moya, J. A. Pomposo,
D. Mecerreyes, Adv. Funct. Mater. 2009, 19, 3326–3333.
[29] M. Ito, K. Koyakumaru, T. Ohta, H. Takaya, Synthesis 1995, 376–378.
[1] Z. Nie, E. Kumacheva, Nat. Mater. 2008, 7, 277–290.
[2] D. Rosenthal, Phys. Status Solidi A 2011, 208, 1217–1722.
[3] Y. Y. Tseng, W.-H. Li, Proc. Natl. Acad. Sci. USA 2012, 109, 1170–1175.
[4] S. H. Anastasiadis, Langmuir 2013, 29, 9277–9290.
[5] E. Gomar-Nadal, J. Puigmartí-Luis, D. B. Amabilino, Chem. Soc. Rev. 2008,
37, 490–504.
[6] A. Proust, B. Matt, R. Villanneau, G. Guillemot, P. Gouzerh, G. Izzet,
Chem. Soc. Rev. 2012, 41, 7605–7622.
[7] T. Darmanin, F. Guittard, Prog. Polym. Sci. 2014, 39, 656–682.
[8] C. Mortier, T. Darmanin, F. Guittard, ChemPlusChem 2014, 79, 1434.
Manuscript received: May 7, 2015
Revised: June 9, 2015
Final Article published: July 16, 2015
ChemPlusChem 2015, 80, 1691 – 1695
www.chempluschem.org
1695
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim