Redox-controlled reversible micelles transition and lyotropic liquid-crystalline behavior of novel polymerizable ferrocenyl surfactants

Article abstract of DOI:10.1016/j.jorganchem.2018.06.001

A novel photopolymerizable surfactant with ferrocenyl group, (11-ferrocenylundecyl) (ethyl methacrylate) dimethylammonium bromide (I⁺), was synthesized through the reaction of 11-bromoundecyl ferrocene and N,N-(dimethylamino) ethyl methacrylate. Based on the results of voltammetric cycle, the small potential difference ΔE was 72 mV, which indicates that the I⁺ has good redox reversibility. The critical micellar concentration (CMC) values were about 0.5 and 22.7 mM for I⁺ in the reduction (CMC_red) and oxidation state (CMC_ox) and it could aggregate and disaggregate by using redox reaction and photopolymerization when its concentrations was between their CMC_red and CMC_ox values. The lyotropic liquid-crystalline properties of I⁺ in water were investigated by X-ray diffraction (XRD) and plarized optical microscope (POM). The results indicate when the concentration of the I⁺ solution over 40 wt %, an ordered lamellar liquid crystal structure was formed. With increasing concentration, the nanoscopic long-range order improved. Moreover, the lyotropic liquid-crystalline properties of I⁺ could also be controlled by using redox reaction and photopolymerization. In a word, the novel polymerizable ferrocenyl surfactants are good environmental responsive materials and can potentially act as the drug carrier and the scavenger for removing dissolved organic impurities in water.

Full text of DOI:10.1016/j.jorganchem.2018.06.001

Journal of Organometallic Chemistry 869 (2018) 81e87
Contents lists available at ScienceDirect
Journal of Organometallic Chemistry
journal homepage: www.elsevier.com/locate/jorganchem
Redox-controlled reversible micelles transition and lyotropic liquid-
crystalline behavior of novel polymerizable ferrocenyl surfactants
,
,
Zhiyu Cheng a, Xueyi Chang a, Yongfu Qiu a *, Guiping Tan a b, Faliang Cheng a,
,
**
Hongbo Fan a, Biye Ren c
a School of Environment and Civil Engineering, Guangdong Engineering and Technology Research Center for Advanced Nanomaterials, Dongguan University
of Technology, Guangdong, 523808, PR China
b Department of Chemistry and Key Laboratory for Preparation, Application of Ordered Structural Materials of Guangdong Province, Shantou University,
Shantou, Guangdong, 523808, PR China
c Research Institute of Materials Science, South China University of Technology, Guangzhou, 510640, PR China
a r t i c l e i n f o
a b s t r a c t
Article history:
A novel photopolymerizable surfactant with ferrocenyl group, (11-ferrocenylundecyl) (ethyl methacry-
late) dimethylammonium bromide (Iþ), was synthesized through the reaction of 11-bromoundecyl
ferrocene and N,N-(dimethylamino) ethyl methacrylate. Based on the results of voltammetric cycle,
Received 3 May 2018
Received in revised form
29 May 2018
Accepted 1 June 2018
Available online 2 June 2018
the small potential difference
D
E was 72 mV, which indicates that the Iþ has good redox reversibility. The
critical micellar concentration (CMC) values were about 0.5 and 22.7 mM for Iþ in the reduction (CMCred
)
and oxidation state (CMCox) and it could aggregate and disaggregate by using redox reaction and pho-
topolymerization when its concentrations was between their CMCred and CMCox values. The lyotropic
liquid-crystalline properties of Iþ in water were investigated by X-ray diffraction (XRD) and plarized
optical microscope (POM). The results indicate when the concentration of the Iþ solution over 40 wt %, an
ordered lamellar liquid crystal structure was formed. With increasing concentration, the nanoscopic
long-range order improved. Moreover, the lyotropic liquid-crystalline properties of Iþ could also be
controlled by using redox reaction and photopolymerization. In a word, the novel polymerizable ferro-
cenyl surfactants are good environmental responsive materials and can potentially act as the drug carrier
and the scavenger for removing dissolved organic impurities in water.
Keywords:
Ferrocenyl group
Photopolymerizable surfactant
Redox-controlled
Reversible micelles transition
Lyotropic liquid-crystalline
© 2018 Elsevier B.V. All rights reserved.
1. Introduction
one of the most important organometallic electron mediators, play
the role of electron transfer between redox matrix and electrode in
The environmental responsive materials by means of the redox
switches, concentration, photochemical and electrochemical, etc.
have recently gained considerable attention due to their potentials
in biosensors, delivery system and energy storage, etc [1e7]. The
surfactant molecules are often used as matrixes of responsive
materials because of their abundant phase structures and manip-
ulative topological structures [8]. Many attempts have been made
to introduce special functional groups into the surfactant's topology
structure that helps to control the formation of molecular self-
assemblies [9]. Ferrocene and its derivatives, owing a redox cen-
electrochemical and biological sensors [10]. Moreover, its synthetic
convenience has attracted the researcher's interest to employ it as a
redox-responsive group in surfactant systems [11e14].
Many researchers have studied the ferrocenyl groups modified
surfactants acting as the drug carrier and the scavenger for
removing dissolved organic impurities in water [15e19]. A problem
facing these applications is the stability of the systems owing to
their dynamic nature. In this paper, we report a novel photo-
polymerizable cationic ferrocenyl surfactant, with good redox
reversibility, stability and its lyotropic liquid-crystalline property in
water being easily controlled by using concentration, redox agents
ter, p-conjugation system, and excellent electron transfer ability, as
* Corresponding author.
** Corresponding author.
E-mail addresses: qiuyf1979@foxmail.com (Y. Qiu), mcbyren@scut.edu.cn (B. Ren).
https://doi.org/10.1016/j.jorganchem.2018.06.001
0022-328X/© 2018 Elsevier B.V. All rights reserved.

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Z. Cheng et al. / Journal of Organometallic Chemistry 869 (2018) 81e87
ferrocene (3) with N,N-(dimethylamino) ethyl methacrylate
through the route outlined in Fig. 2, according to similar method
previous reported with slight improvement [21]. To a three-neck
100 mL round-bottom flask with a Teflon-coated magnetic stirring
bar, a mixture of N,N-(dimethylamino) ethyl methacrylate (1.6 g,
10.1 mmol), and 11-bromoundecyl ferrocene (3.2 g, 7.6 mmol) in
40 mL of acetone was added. The mixture was firstly refluxed under
vigorous stirring for approximately 72 h in Ar atmosphere and thin-
layer chromatography (TLC) analysis was used to indicate the end of
the reaction; then, filtered at about 50 ꢀC and the filtrate were
concentrated. The resultant solid was purified by column chroma-
tography using dichloromethane/methanol (10/1) to afford a golden-
yellow solid compound Iþ (3.1 g, yield 70%). Rf ¼ 0.78 (dichloro-
methane/methanol (5/1)).1H NMR (CDCl3, TMS,
d, ppm) of ferrocenyl
surfactants Iþ was shown in Fig. 3: 6.14 [s, 1H, -C (CH3) ¼ CH2 cis to
C¼O], 5.66 [s,1H, -C(CH3) ¼ CH2 trans to C¼O], 4.66 (t, 2H, -CO2-CH2-
), 4.13 (m, 2H, -CO2-CH2-CH2- N), 4.03e4.08 (m, 9H, H(Cp)), 3.61 (t,
2H, -CH2-CH2 -CH2-N), 3.45 [s, 6H, (CH3)2-N], 2.31 (t, 2H, Cp-CH2-),
1.95 (s, 3H, -C(CH3) ¼ CH2), 1.75 (m, 2H, -CH2-CH2-CH2-N), 1.26e1.51
(m, 16H, -(CH2)8-CH2-CH2-N). Anal. Calcd. For C29H46NBrFeO2
(576.43): C, 60.43; H, 8.04. Found: C, 60.18; H, 8.09.
2.3. Redox response of Iþ
Fig. 1. The electron transfer reaction of polymerizable ferrocenyl surfactants (the
In general, chemical or electrochemical redox methods were
used to prepare oxidized/reduced form solution of ferrocenyl sur-
factants. In our research, blue solutions of I2þ (oxidized state) were
prepared by addition of 0.52 M equiv of iron sulfate (Fe2(SO4)3), the
reduced forms of ferrocenyl groups, Iþ, and the oxidized forms, I2þ.).
and photopolymerization. The electron transfer reaction of poly-
merizable ferrocenyl surfactant with the reduced forms Iþ and the
oxidized forms I2þ are shown in Fig. 1.
oxidant, to yellow solutions of Iþ (reduced state). To reduce the I2þ
,
vitamin C (0.52 M equiv) was added to blue solutions of I2þ and
stirred until the yellow color solutions of Iþ was reformed.
2. Experimental
2.4. In situ photopolymerization of Iþ
2.1. Materials
A mixture of a D2O solution of Iþ, a photoinitiator (DMPA,1 wt %)
and cross-link agent (DAP, 0 or 2 wt %) was placed in a 10 mL flask.
The mixture was bubbled with argon for 30 min, and sealed with a
rubber septum. The mixture was polymerized by photoirradiation
with a high-press UV lamp (mercury arc lamp, 3 mW cmꢁ2) under
argon protection at room temperature. The process of in situ
polymerization was monitored by means of checking the diminu-
tion of vinyl signals in the 1H NMR spectrum of a sample solution
prepared in D2O. The completion of polymerization was confirmed
by the disappearance of vinyl protons signals in the 1H NMR
spectrum. This in situ photoirradiation process was maintained for
10 min to complete the polymerization. These samples with cross-
link agent (DAP, 0 or 2 wt %) in reduced state after photo-
polymerization were denoted as PIþ-0 and PIþ-2, while their cor-
responding oxidized state were denoted as PI2þ-0 and PI2þ-2.
11-Bromoundecanoic acid (98%), ferrocene (98%), 2,2-
dimethoxy-2- phenylacetophenone (DMPA, 99%), diallyl phthalate
(DAP, 97%) and N,N-(dimethylamino) -ethyl methacrylate (98%)
were purchased from Aldrich and used as received. Doubly distilled
water was used for all solutions. The synthesis of 11-bromoundecyl
ferrocene (compound 3 in Fig. 2.) was reported in our previous
study in detail [20]. Other reagents were commercial chemicals of
analytical grade and purified following the standard procedure.
2.2. Synthetic procedures of (11-ferrocenylundecyl) (ethyl
methacrylate) dimethylammonium bromide (Iþ)
(11-ferrocenylundecyl) (ethyl methacrylate) dimethylammonium
Bromide (Iþ) was synthesized using the reacting 11-bromoundecyl
Fig. 2. Synthetic routes of 11-bromoundecyl ferrocene (3), and polymerizable ferrocenyl surfactants (Iþ).

Z. Cheng et al. / Journal of Organometallic Chemistry 869 (2018) 81e87
83
Fig. 4. Cyclic voltammograms of the Iþ with scan rate of 10 mV sꢁ1 in 0.01 M NaBr
aqueous solution at room temperature.
Fig. 3. 1H NMR spectra of polymerizable ferrocenyl surfactants (Iþ) in CDCl3 solvent.
2.5. Measurements
0.093 V are observed. The small potential difference
D
E (¼ Epa - Epc
)
is 72 mV, which indicates that the Iþ have good redox reversibility.
The good redox-response self-assembly behavior of Iþ in
aqueous solution can be regulated through adding oxidants and
reducing agents. Fig. 5 is the UVevis spectra for oxidation and
reduction state of ferrocenyl surfactant Iþ aqueous solution. The
absorption peak at 440 and 628 nm belong to the ferrocene units
(in reduction state, yellow) and ferrocenium (in oxidation state,
blue), respectively. When a small excess of oxidant Fe2(SO4)3 was
added into Iþ aqueous solution, the absorption peak at 440 nm
disappeared and the absorption peak at 628 nm appeared, indi-
cating the ferrocene units were oxidized to ferrocenium. In turn,
once the reducing agent vitamin C was added, the ferrocenium was
reversibly reduced to ferrocene units again.
1H NMR spectrum of Iþ was obtained in CDCl3 or D2O solution
on a Varian INOVA 500NB spectrometer. The carbon, hydrogen and
nitrogen contents (wt %) of Iþ were determined with a Vario EL
elemental analyzer. Cycltammograms (CV) measurements of Iþ
were performed on a CHI 660 electrochemical workstation (CH
Instruments, Shanghai) in 0.01 M NaBr aqueous solution using a
three-electrode system at room temperature. The glassy carbon
was used as the working electrode, a platinum wire as the counter
electrode, and saturated calomel as the reference electrode (SCE).
The sweep range was from ꢁ0.05 V to þ0.3 V versus the SCE.
UVevisible absorbance of Iþ and I2þ were measured with a Hitachi
UV-3010 spectrophotometer. Surface tensions of Iþ and I2þ were
tested from a surface tension meter (Dataphysics OCA20, Germany)
at 25 ꢀC. Transmission electron microscopy (TEM) photographs
were collected from a JEM-2100HR Microscope, and samples were
prepared on the cellulose-coated copper grids by aero-spray
method and then stained by 1.5 wt % uranyl acetate aqueous so-
lution. The size distribution of Iþ and I2þ was measured with a
Malvern Nano-ZS 90 Zetasizer, using a monochromatic coherent
He-Ne laser (633 nm) as the light source and a detector that
detected the scattered light at 90ꢀ. X-ray diffraction (XRD) of the
aqueous solution of Iþ and I2þ was performed with an X'pert PRO
3.2. Critical micellar concentration (CMC) of monomer surfactant Iþ
in aqueous solution
We know that Iþ in aqueous solution has good redox-response
diffractometer using Cu Ka radiation (wavelength
l
¼ 0.154 nm) at
room temperature. The samples were prepared by filling the thin
glass bath (10 ꢂ 10 ꢂ 3 mm 3). The 2
q
ranged from 1ꢀ to 10ꢀ and the
scan step was 0.01ꢀ in 2
q .
with a counting time of 1 s stepꢁ1
Polarized optical microscope (POM) of Zeiss Axiophot was used at
room temperature.
3. Results and discussion
3.1. Redox activity of monomer surfactant Iþ in aqueous solution
In order to study the redox activity property of the ferrocenyl
surfactant, electrochemical behavior of Iþ with CV technique in
0.01 M of NaBr aqueous solution was performed. The CV curves of
1 mM ferrocenyl surfactant Iþ aqueous solution at a scan rate of
10 mV sꢁ1 within the potential range of ꢁ0.05 to þ0.3 V at room
temperature are shown in Fig. 4. A couple of redox peaks for anodic
peak potential Epa at 0.165 V and cathodic peak potential Epc at
Fig. 5. UVevis spectra for aqueous solutions of ferrocenyl surfactant Iþ before and
after chemical redox by Fe2(SO4)3 and vitamin C.

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Z. Cheng et al. / Journal of Organometallic Chemistry 869 (2018) 81e87
reaction when the concentrations of Iþ is between their CMCred and
CMCox values. That is, a redox-controlled reversible self-assembly
process may be established by redox reaction of ferrocenyl
groups if only the concentrations of Iþ is between CMCred and
CMCox
.
3.3. Redox response reversible micelles transition of PIþ and PI2þ
PIþ-0 and PIþ-2 are the samples of Iþ after photopolymerization
with concentration of 0 and 2 wt % cross-link agent DAP. 1.0 mM of
aqueous solution was selected since which is between their CMCred
(0.5 mM) and CMCox (22.7 mM). These samples and concentration
are selected in order to study conveniently their redox-controlled
reversible self-assembly behaviors. In Fig. 7a, PIþ-0 spherical mi-
celles with 8 nm in diameter were observed. As expected, the
spherical micelles were totally disassembled into discontinuous
fragments after oxidation by Fe2(SO4)3 (Fig. 7b) and then spherical
micelles with 8 nm in diameter reversibly recovered under reduc-
tion by vitamin C (Fig. 7c). As the same, the PIþ-2 spherical micelles
diameter at initial is 12 nm (Fig. 7d); the swollen spherical micelles
diameter became 17 nm after oxidation by Fe2(SO4)3 (Fig. 7e),
which is due to the expansion of the adding crosslinking agent;
finally, the spherical micelles with 12 nm in diameter were
reversibly recovered after reduction by vitamin C (Fig. 7f).
Fig. 6. Dependence of equilibrium surface tentisons (g
) on concentration of Iþ (-,
reduced state) and I2þ(C, oxidized state) in aqueous solutions.
self-assembly behavior. How to use this behavior to control their
self-assemble into micelles? The critical micellar concentration
(CMC) values of the ferrocenyl surfactant Iþ are the critical factors
to be studied. The CMC values were observed by using the surface
tension method and they are about 0.5 and 22.7 mM for Iþ in the
reduction and oxidation state shown in Fig. 6. The CMC of Iþ in the
oxidation state (denoted as CMCox) is approximately equal to 45
times than its CMC of Iþ in the reduction state (denoted as CMCred),
indicating the hydrophilicity of ferrocenium cations is enhanced,
which is consistent with other ferrocenyl surfactants [21]. The re-
sults suggest that Iþ could aggregate and disaggregate by redox
The redox-controlled reversible self-assembly behaviors for PIþ-
0 and PIþ-2 were further confirmed by DLS shown in Fig. 8. The
micelles diameters of PIþ-0 and PIþ-2 became larger after oxidation
by Fe2(SO4)3 and then return to the original size upon reduction by
vitamin C. The variations in the morphology and size of aggregates
of PIþ-0 and PIþ-2 are attributed to the oxidation reactions of
ferrocene groups. The transformation of the hydrophobic ferrocene
groups to the hydrophilic ferrocenium salt enhances the
Fig. 7. TEM images of (a) PIþ-0 micelles; (b) irregular fragments of PI2þ-0 oxidized by Fe2(SO4)3; (c) reduced by vitamin C from PI2þ-0 in 1.0 mM aqueous solutions; (d) PIþ-2
micelles; (e) PI2þ-2 swollen micelles after oxidation by Fe2(SO4)3 and (f) reduction by vitamin C in1.0 mM aqueous solutions.

Z. Cheng et al. / Journal of Organometallic Chemistry 869 (2018) 81e87
85
40 wt% indicating the formation of an ordered lamellar liquid
crystal structure. These three diffraction peaks are indexed to the
planes (001), (002) and (003) and they become stronger with
increasing concentration, suggesting that the higher concentration
improves the nanoscopic long-range order.
In order to realized the effect of outside stimulus such as
oxidation and polymerization of Iþ to its lyotropic liquid crystal
behavior, 50 wt % Iþ aqueous solution as a representative was
examined. 50 wt % Iþ aqueous solution with an ordered lamellar
liquid crystal structure can be seen in Fig. 10a. When some
Fe2(SO4)3 solution added into, the three diffraction peaks dis-
appeared (Fig. 10b), which indicated that the ordered lamellar
mesomorphous structure was destroyed. This is because the hy-
drophobic ferrocene groups are transformed to the hydrophilic
ferrocenium salt, which maked the lamellar liquid crystal no longer
stable and then turned into amorphous structure.
In Fig. 10c, when Iþ were photopolymerization into PIþ-0, the
three diffraction peaks became very weak, suggestting that the
degree of ordered stacking structure reduced with the completion
of photopolymerization process. In Fig. 10d, the XRD diffraction
peak disappeared for PI2þ-0 aqueous solution after PIþ-0 oxidation
by Fe2(SO4)3, which indicated that weak cross-linking lamellar
liquid crystal structure was destroyed. This is also because the hy-
drophobic ferrocene groups are transformed to the hydrophilic
ferrocenium salt, which maked the lamellar liquid crystal turnning
into amorphous structure.
Fig. 8. Size distribution of (a) PIþ-0 micelles and (b) PIþ-2 by using dynamic light
scattering (DLS) in 1.0 mM aqueous solutions, for oxidation-reduction cycle.
hydrophilicity of molecular chains. These results provide an effec-
tive approach to the redox-controlled reversible self-assembly of
PIþ and PI2þ systems without changing their molecular structure.
3.4. Redox-controlled lyotropic liquid-crystalline (LLC) phase
behavior
The lyotropic liquid-crystalline properties of Iþ in water were
investigated by XRD. In Fig. 9, no obvious diffraction peak was
observed when the concentration of the Iþ solution at 30 wt % and
three diffraction peaks could be found once the concentration over
Fig. 9. XRD profiles for the Iþ aqueous solution in the concentration of 30, 40, and
Fig. 10. XRD profiles for (a) Iþ, (b) I2þ, (c) PIþ-0, (d) PI2þ-0, in the concentration of
50 wt %.
50 wt % in water.

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Z. Cheng et al. / Journal of Organometallic Chemistry 869 (2018) 81e87
Fig. 11. Polarized optical micrographs of the surfactant aqueous solution at room temperature: (a) the 30 wt% Iþ aqueous solution, (b) the 40 wt% Iþ aqueous solution, (c) the 50 wt%
Iþ aqueous solution, (d) the 50 wt% I2þ aqueous solution,(e) the 50 wt% PIþ-0 aqueous solution, (f) the 50 wt% PI2þ-0 aqueous solution.
Further, It is significant to directly observe the lamellar liquid
crystal phase with a POM. An isotropic phase without birefringent
texture is observed from the Iþ solution when the concentration is
30 wt % (Fig. 11a). As expected, when the concentration is 40 and
50 wt %, the Iþ solution exhibit the birefringent random polygon-
like texture (Fig. 11b and c), which corresponding to lamellar
smectic A or C (SmA or SmC) liquid-crystalline phase. More ordered
stacking lamellar liquid-crystalline structure in the Iþ solution is
observed with increasing concentration. Then, as expected, an
isotropic phase without birefringent texture is observed from the
50 wt % I2þ aqueous solution (Fig. 11d), which indicated lamellar
smectic A or C (SmA and SmC) liquid-crystalline phases were
disappear after Iþ was oxided by Fe2(SO4)3. The POM optical tex-
tures of PIþ-0 aqueous solution are shown in Fig. 11e, it is obvious
that the lamellar SmA and SmC liquid-crystalline phase were being
maintained upon photopolymerization. However, an isotropic
phase was observed from the PI2þ-0 aqueous solution, which
indicated lamellar SmA and SmC liquid-crystalline phases dis-
appeared after oxidation by Fe2(SO4)3 (Fig. 11f). The POM results are
in good agreement with the results obtained by XRD. We can see
that the lyotropic liquid-crystalline properties of Iþ in water could
be easily controlled by using concentration, redox agents and
photopolymerization.
Based on the results of voltammetric cycle, the small potential dif-
ference
D
E (¼ Epa - Epc) is 72 mV, which indicates that the Iþ have
good redox reversibility. The critical micellar concentration (CMC)
values were observed by using the surface tension method and they
are about 0.5 and 22.7 mM for Iþ in the reduction and oxidation state.
The results of dynamic light scattering (DLS) and transmission
electron microscopy (TEM) suggest that Iþ could aggregate and
disaggregate by using redox reaction and photopolymerization when
the concentrations of Iþ is between their CMCred and CMCox values.
The lyotropic liquid-crystalline properties of Iþ in water were
investigated by X-ray diffraction (XRD) and polarized optical mi-
croscope (POM). The results indicate when the concentration of the
Iþ solution over 40 wt %, an ordered lamellar liquid crystal structure
was formed. With increasing concentration, the nanoscopic long-
range order improved. Moreover, the lyotropic liquid-crystalline
properties of Iþ could also be controlled by using redox reaction
and photopolymerization. In a word, the novel polymerizable fer-
rocenyl surfactants are good environmental responsive materials
and can potentially act as the drug carrier and the scavenger for
removing dissolved organic impurities in water.
Acknowledgements
The work described in this paper was supported by the Tech-
nology Planning Project of Guangdong Province (No.
2016B090918006 and 2015B090927007), the Guangdong Innovation
Team Project for Colleges and Universities (No. 2016KCXTD023), the
National Natural Science Foundation of China (No. 21674039), Dr.
Guiping Tan acknowledges the finance support from the Guangdong
Natural Science Foundation (No.2015A030310242) and Key
4. Conclusions
A novel photopolymerizable surfactant with ferrocenyl group,
(11-ferrocenylundecyl) (ethyl methacrylate) dimethylammonium
bromide (Iþ), was synthesized through the reaction of 11-bro-
moundecyl ferrocene and N,N-(dimethylamino) ethyl methacrylate.

Z. Cheng et al. / Journal of Organometallic Chemistry 869 (2018) 81e87
87
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