The Journal of Adhesion

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DTT functionalization of Ag particles for

conducting adhesives

Cristian S. de Oliveira, Luis T. Quispe, Cristiani C. Plá Cid, Jelver A. Sierra,

Silvio de Barros, A. Mello & André A. Pasa

To cite this article: Cristian S. de Oliveira, Luis T. Quispe, Cristiani C. Plá Cid, Jelver A. Sierra,
Silvio de Barros, A. Mello & André A. Pasa (2017): DTT functionalization of Ag particles for
conducting adhesives, The Journal of Adhesion, DOI: 10.1080/00218464.2017.1288113

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THE JOURNAL OF ADHESION
http://dx.doi.org/10.1080/00218464.2017.1288113

DTT functionalization of Ag particles for conducting

adhesives
Cristian S. de Oliveiraa,b, Luis T. Quispea, Cristiani C. Plá Cida, Jelver A. Sierraa,
Silvio de Barros c, A. Mellod, and André A. Pasaa
a
Laboratório de Filmes Finos e Superfícies, Departamento de Física, Universidade Federal de Santa
Catarina, Florianópolis, SC, Brazil; bInstituto Federal de Educação, Ciência e Tecnologia do Rio Grande
do Sul - Campus Farroupilha, Farroupilha, RS, Brazil; cCentro Federal de Educação Tecnológica Celso
Suckow da Fonseca, Rio de Janeiro, Brazil; dCentro Brasileiro de Pesquisas Fısicas, Rio de Janeiro, Brazil

ABSTRACT ARTICLE HISTORY

We have studied the influence of the organic molecule DL- Received 24 November 2016
Dithiothreitol on the properties of isotropic conductive adhe- Accepted 25 January 2017
sives for application in microelectronics. The Ag fillers were KEYWORDS
prepared from commercial micro flakes or submicron particles Conductive adhesives;
from waste jewelry. The results show that coating of the Ag recycling; surface treatment
recycled fillers with thiol avoided the agglomeration of the
particles improving the dispersion and the electrical and
mechanical properties. By comparing the samples, the better
properties were obtained from adhesives with recycled Ag
particles relative to the ones formulated with commercial Ag
flakes and improvement can be attributed to the absence of
the lubricant layer and smaller size of the particles produced
from recycled silver.

1. Introduction
In microelectronics packaging with tin-lead solders is normally used.
However, lead is harmful to the environment and human being, leading
to a global concern about the search for alternative solders free of this
element [1,2]. Moreover, nowadays microelectronic devices are becoming
smaller and needing fine pitch connections and the current solder alloy
could cause defects such as bridging and solder ball [2]. One potential
alternative for replacement of tin-lead solders is the use of electrically
conductive adhesives (ECAs) composed by a polymeric matrix and con-
ductive fillers that are responsible for the mechanical properties and elec-
trical conduction, respectively [3]. These adhesives are classified according
to the percolation threshold for electrical conduction that is quantified by
the percentage of the volume fraction of filler and varies in the range from
15% to 25%. If the adhesive has an amount of filler smaller than

CONTACT André A. Pasa andre.pasa@ufsc.br Universidade Federal de Santa Catarina, Física, Campus
Universitário, Caixa Postal 476, Florianopolis, 88040-900 Brazil.
Color versions of one or more of the figures in this article can be found online at www.tandfonline.com/gadh.
© 2017 Taylor & Francis
2 C. S. DE OLIVEIRA ET AL.

percolation threshold, it is classified as an anisotropic conductive adhesive

(ACA) and will conduct electric current in one direction. If the percentage
of filler is above the percolation threshold, it is classified as an isotropic
conductive adhesive (ICA) and will conduct current in all directions [4,5].
Common conductive fillers used in ECAs are micro-sized silver particles in
the form of flakes. The metal silver is chosen because of its high electrical
conductivity, good processability, and native conductive oxide, with the
disadvantage of being relatively expensive [5]. Most of the commercially
available particles are produced by grinding or milling processes that leave
a thin organic layer of lubricant on the surface of the particles. This layer
of a fatty acid such as the stearic acid is important for the dispersion of the
flakes in the adhesive with the disadvantage of reducing the conductivity of
ECAs [6,7]. An alternative for this drawback is to remove the insulating
layer or to replace it by other chemical compounds. Lu et al. [7] showed
that the use of short-chain acids, diethylene glycol butyl ether and poly
(ethylene glycol), partially replaces the lubricant layer, improving the elec-
trical conductivity of ECAs. The functionalization of Ag surface with
hexanedioic acid improved electrical and mechanical properties of ICAs
[8]. Li et al. [9] replaced partially or completely the surfactant stearic acid
by short-chain dicarboxylic acids and observed that malonic and adipic
acids improved significantly the conductivity of the adhesive without
affecting the physical and mechanical properties. In this case, the improve-
ment was attributed to the single-bond short chain between the dicar-
boxylic groups, which allows better electron transport between silver
flakes. On the other hand, terephthalic acid with a benzene ring between
the dicarboxylic groups reduced the conductivity of the samples.
Other studies also investigated the electrical conductivity of ECAs con-
taining fillers functionalized by organic molecules. Li et al. [10] investi-
gated two types of organic layers, dicarboxylic acid, and dithiol and
observed that the electrical properties of adhesives were significantly
improved. Zhang et al. [11] used 4,4ʹ-biphenyldithiol for the treatment
of Ag particles and Au-coated polymer particles with an improvement in
electrical properties of ACA formulations. Li et al. [4,12] studied three
types of alkanethiol molecules as an organic coating for Au and Ag fillers
and detected better electrical performance of the adhesive. The organic
molecules forming bonds with the metal surface reduce the electrical
resistance of the ECAs.
In this work, we investigated the use of the organic molecule DL-
Dithiothreitol (DTT), an α,ω-alkanedithiol with a short carbon chain, for
the replacement of the lubricant layer present in commercial micro-sized
silver particles and compared the results with particles obtained from
recycled silver. The two kinds of silver particles were tested in ICA formula-
tions with 80 wt % (30.3% volume fraction) of filler.
 THE JOURNAL OF ADHESION 3

2. Experiments
2.1. Materials
Acetone purchased from Química Moderna (Barueri, Brazil), ethyl alcohol
99.5% from Labsynth (Diadema, Brazil), and detergent from Sigma-Aldrich
(São Paulo, Brazil) were used to clean the waste jewelry. Nitric acid (HNO3)
obtained from Labsynth, sodium chloride (NaCl) from Labsynth, and sodium
borohydride (NaBH4) 99% from Sigma-Aldrich were used for recycling silver
powder. Ethanol ≥99.8% purchased from Sigma-Aldrich and DTT ≥99.8%
from Sigma-Aldrich were used for functionalization of silver particles. Epoxy
bisphenol A diglycidyl ether (DGEBA), curing agent tetraethylenepentamine
(TEPA), and solvent isopropyl alcohol 99.5% were purchased from Sigma-
Aldrich and used for the formulation of the polymer matrix. Silver flakes
with an average diameter of 10 μm, 99% of purity, were obtained from
Sigma-Aldrich to be used as filler in the adhesives. Commercial electrical
conductive adhesive Loctite 3880 was purchased from Loctite Co. for elec-
trical and mechanical characterization.

2.2. Recycling silver jewelry

Waste jewelry was cut into small pieces with an average size of 0.5 cm and
heated in detergent solution at 100°C for 1 hr. After this procedure, the
pieces were rinsed in deionized water and cleaned in an ultrasonic bath
with deionized water, acetone, and ethyl alcohol, in this sequence, then
dried at 60°C for 1 hr. For each 1 g of clean jewelry, the following
sequence of steps was used to produce the Ag powder. The Ag pieces
were immersed in 20 ml of a solution of deionized water and HNO3 at a
ratio of 3:1 under mechanical stirring for 1 hr to promote the formation of
silver nitrate (AgNO3). Then, 0.54 g of NaCl was added to the solution
that was mechanically stirred for 20 min to promote the further formation
of silver chloride (AgCl). The AgCl (s) was filtered from the solution and
dried for 1 hr at 60°C. The dried AgCl (1 g) was added to a solution
containing 300 mg of NaBH4 in 50 ml of deionized water at 60°C and the
solution was mechanically stirred for 1 hr [13]. The solution becomes gray
indicating the formation of metallic silver powder that was filtered and
washed with deionized water and ethanol. The powder is dried in air at
60°C for 5 hr.

2.3. DTT surface treatment

The commercial and recycled silver powders were treated in solutions con-
taining DTT dissolved in ethanol at 0.1, 1, and 10 mM during 24 hr at room
temperature. After treatment, the particles were centrifuged and redispersed
4 C. S. DE OLIVEIRA ET AL.

in ethanol three times to remove non-adhering DTT molecules. Finally, the

Ag particles coated with DTT were air dried at 50°C for 12 hr.

2.4. Preparation of ICAs

The polymer matrix was prepared from epoxy resin DGEBA and curing
agent TEPA in a weight ratio of 3:1. These compounds were mixed with
150 μl of isopropyl alcohol with vortex mixing for 8 min and ultrasonic bath
for 8 min and then the treated and untreated silver particles (fillers), pre-
viously sieved in sieves with aperture sizes of 20 μm, were added to the
polymer matrix by vortex mixing for 4 min and ultrasonic bath during 4 min.
Finally, the adhesive was flushed with nitrogen gas for the evaporation of the
solvent. The content of silver filler was fixed at 80% by weight.

2.5. Preparation of samples for bulk resistivity and shear strength test
For the electrical measurements, the prepared conductive pastes were printed
by screen-printing in a rectangular area defined by a mask tape on a glass
substrate. After removal of the mask, the strips of ICA of length a, width d,
and thickness w are pre-cured at 50°C for 20 min and cured at 140°C for 2
hr. The resistivity of the cured ICA strips was measured using a Keithley
2400 Source Meter with a 4-point probe with a distance s between the tips.
The current (I) is applied between the two outer probes and the voltage (V)
measured between the two inner probes. The electrical resistivity (ρ) is
calculated from the following equation:
ρ ¼ ρs w; (1)
where ρs is the sheet resistivity given by
 
V a d
ρs ¼ C ; ; (2)
I d s


where C da ; ds is a correction factor dependent on the sample dimensions
and distance between probes [14]. For using Equation (2) the samples
were prepared considering the following restrictions: ds >1, da  4,
and ws <0:4.
For shear strength tests, the samples were made according to the D1002
standard. With the purpose of mimicking practical application, the shear
strength samples were prepared on pieces of FR-1 printed circuit board with
a single coppered face. The test samples were prepared by coating the copper
side of one piece with ICAs paste. The piece with the ICAs is then pressed
against the coppered surface of the second piece with a constant normal force
 THE JOURNAL OF ADHESION 5

of 80 N at 50°C during 20 min and 140°C for 2 hr. The shear strength (σ) is
calculated from Equation (3):
f
σ¼ ; (3)
A
where f is the force applied parallel to the surface of the test sample to break off
the bond, and A is the area covered by the adhesive. Tests were carried out
using a testing system Instron 5966 (Norwood, USA) equipped with a 10-KN
load cell.

2.6. Surface, composition, and morphological characterization

Scanning electron microscopy (SEM) of the silver particles and ICAs was
carried out with a JEOL JSM-6701F field-emission scanning microscope
(FESEM) and JEOL JSM-6390LV scanning electron microscope. All samples
investigated by SEM were covered with a gold layer of ~10 nm.
Atomic absorption spectroscopy was used for elemental analysis and
carried out with atomic absorption spectrometer with flame model
contrAA®700, AnalytikJena, Germany. The X-ray photoelectron spectroscopy
(XPS) analysis was done in a SPECS PHOIBOS 100/150 spectrometer with a
150-mm hemispherical analyzer at an X-ray energy of 1486.6 eV. The bind-
ing energies were calibrated with the C 1s peak at 284.8 eV. The individual
element spectrum for S 2p3/2 and 2p1/2 was obtained with an energy step
size of 0.05 eV and pass energy of 25.0 eV.
The contact angle of a drop of deionized (DI) water on the surface of discs
prepared by pressing the Ag particles was measured to determine the wetting
properties of the samples using a goniometer Ramé-Hart 250 Instrument Co.

3. Results and discussion

3.1. DTT coverage
In order to check if the Ag particles were covered with DTT after the
incubation process, the contact angle was measured on samples with and
without DTT treatment. Table 1 presents the contact angle values obtained
for a DI water droplet on the surface of disks from pressed commercial or

Table 1. Contact angles of silver particles before and after treatment

with DTT.
Silver particles Contact angle (°)
Ag commercial – untreated 108.1 ± 0.5
Ag commercial – 10 mM DTT 52.4 ± 3.8
Ag recycled – untreated 67.7 ± 5.7
Ag recycled – 0.1 mM DTT 60.1 ± 4.4
Ag recycled – 10 mM DTT 30.2 ± 4.9
6 C. S. DE OLIVEIRA ET AL.

recycled silver particles. The high contact angle of 108.1° for untreated
commercial silver particles is attributed to the presence of the lubricant
layer. The incubated commercial particles with 10 mM DTT showed a
much lower contact angle of 52.4° indicating the replacement of the lubricant
layer by the thiol molecules, which have hydrophilic groups in its structure
(–SH and –OH). The DTT molecule has two possibilities of assembling on
metallic surfaces, i.e., standing up or lying down. In the standing-up config-
uration, the molecule binds to the surface via one Au-S bond and the other
thiol group remains exposed. However, from the literature the lying-down
configuration is the expected one [15–17].
The results for the contact angle of recycled silver particles, obtained by
following the procedure discussed in Section 2.2, untreated and treated in
0.1 mM DTT show higher angles than commercial Ag treated with 10 mM
DTT. Surfaces with no lubricant or low coverage with DTT explain the
measured angles. However, the higher hydrophilicity of recycled Ag particles
treated with 10 mM DTT with a contact angle of 30.2° shows that the absence
of the lubricant layer allowed an increase in DTT surface coverage. In
addition, the relatively high contact angle of 52.4° for treated commercial
Ag, as discussed above, is an indication that the lubricant was only partially
replaced by the DTT.
The chemical surface composition of recycled silver particles treated with
10 mM DTT was measured with XPS and the results are shown in Figure 1.

Figure 1. XPS S2p signal of recycled silver particles incubated with 10 mM DTT with the S 2p3/2
signal fitted with three different sulfur species with binding energies of 160.9, 161.8, and 163.4 eV, for
chemisorbed sulfur (S-Ag), surface thiolate (-R-S-Ag), and unbound DTT species (R-S-H), respectively.
 THE JOURNAL OF ADHESION 7

A broad S2p signal between 160 and 166 eV is observed and indicates the
presence of DTT molecules on the surface of Ag. The S2p signal has a
doublet structure due to p1/2 and p3/2 levels, with a spin-orbit splitting of
1.18 eV and area ratio of 1:2. The broad peak in the figure can be fitted by
doublets with S2p3/2 binding energy at 160.9, 161.8, and 163.4 eV, corre-
sponding to chemisorbed sulfur (S-Ag), surface thiolate (-R-S-Ag), and
unbound DTT species (R-S-H), as described by Battocchio et al. [18]. The
intensities of peaks at 161.8 and 163.4 eV can provide information about
DTT molecule configuration on the silver surface. The higher intensity at
161.8 eV denotes the prevalence of lying-down configuration because it is
related to -S–Ag covalent bonds relative to the lower intensity at 163.4 eV,
which corresponds to free SH groups, and assigned to standing-up molecules.
For silver particles incubated with 0.1 mM DTT, a weak XPS S2p signal was
observed (data not shown), suggesting that the Ag surfaces are less covered
with DTT molecules; a result that is in agreement with the measured contact
angles values, which are higher when compared to samples treated with more
concentrated DTT solutions, as described above.

3.2. Morphology of particles and ICAs

Figure 2a and b shows images of commercial Ag particles untreated and
treated with 10 mM DTT, respectively. The particles were imaged on the

Figure 2. SEM results: (a) and (b) are top view images of commercial Ag flakes untreated and
treated with 10 mM DTT, respectively. (c) and (d) are cross-sectional images of the ICAs prepared
with 80 wt % of filler untreated and treated in 10 mM DTT, respectively.
8 C. S. DE OLIVEIRA ET AL.

surface of a carbon tape and flakes isolated or in agglomerates are observed.

The estimated diameter of the particles for these samples was in the range
between 1 and 4 μm. Figure 2c and d are cross-sectional images showing a
similar morphology of the ICAs prepared with 80 wt % of filler from
commercial particles with and without treatment in 10 mM DTT. From
the point of view of morphology, the incubation with DTT brings no
significant changes in the adhesives with commercial Ag, once once in the
case without DTT the lubricant coats the surface of the flakes.
Figure 3 shows SEM images of particles obtained from recycled Ag. For
samples as prepared and incubated with 0.1 mM DTT (see Figure 3a and b),
small particles with sizes in the range of 0.2–1 µm are observed forming large
agglomerates with sizes of about 10 µm. The incubation with higher con-
centrations of 1 and 10 mM DTT avoided the formation of the large
agglomerates and the small particles can be seen disaggregated on the surface
of the carbon tape, as shown in Figure 3c and d, respectively. This last result
confirms that the DTT coverage is higher for particles treated in 1 and
10 mM DTT, avoiding the aggregation and in agreement with contact
angle and XPS results described above. It is important to note that the
particles produced by the recycling method are much smaller than the one
acquired commercially, as can be observed by comparing Figures 2 and 3.

Figure 3. SEM top view images of recycled samples (a) untreated and treated with (b) 0.1, (c) 1,
and (d) 10 mM DTT.
 THE JOURNAL OF ADHESION 9

Figure 4. SEM top view images of adhesives filled with recycled Ag (a) untreated and treated
with (b) 0.1, (c) 1, and (d) 10 mM of DTT.

Figure 4 displays top view images of ICAs filled with 80 wt % of recycled

Ag particles. From the morphology of the samples shown in Figure 4a and b,
we can observe that the adhesives were formed maintaining the large clusters
shown in Figure 3a and b. For adhesives prepared with recycled Ag particles
submitted to higher concentrations of DTT, more homogeneous and uni-
form layers are obtained, where the particles are completely dispersed, as can
be seen in Figure 4c and d for 1 and 10 mM, respectively.
Figure 5 is a cross-sectional view of the adhesive prepared with recycled
Ag treated with 10 mM of DTT, confirming that the layers are homogeneous
and uniform also in the bulk, showing a good dispersion in the polymeric
matrix.

3.3. Electrical resistivity

Figure 6 shows the general results for the electrical resistivity of ICAs filled
with 80 wt % of commercial or recycled silver particles with or without DTT
treatment. For untreated commercial flakes, it is evident that the lubricant
coverage on the surface of the particles significantly affects the electrical
resistivity and values of about 21 × 10−4Ω cm were measured. Due to the
absence of the lubricant layer, a lower resistivity value was obtained for the
adhesive with untreated recycled Ag particles of about 6 × 10−4Ω cm. The
10 C. S. DE OLIVEIRA ET AL.

Figure 5. Cross-sectional view of the adhesive prepared with recycled Ag treated with 10 mM
DTT.

Figure 6. Electrical resistivity of ICAs filled with 80 wt % of recycled (circles) or commercial

(squares) Ag particles as a function of DTT concentration.

adhesives with DTT-treated fillers presented resistivity values equal or below

2 × 10−4Ω cm, being the lowest values observed for recycled Ag treated with
1 and 10 mM of DTT. The resistivity values obtained in this work for the
 THE JOURNAL OF ADHESION 11

ICAs are comparable to the existing commercial ICAs and to values from the
literature that are in the range of 1–5 × 10−4Ω cm [19, 20]. The ICAs
prepared with recycled Ag fillers treated with DTT showed slightly better
electrical performance than those filled with treated commercial Ag flakes.
The absence of lubricant layer and the smaller size of recycled Ag particles
allowed better coverage with DTT and better dispersion in the adhesive,
which are probably the reasons for the lower resistivities observed.

3.4. Shear strength

Figure 7 shows the shear strength of ICAs filled with commercial or recycled Ag
particles as a function of DTT concentration. For comparison, we presented the
shear strength of 2.4 MPa of the adhesives formulated without filler for 3:1 ratio
DGEBA to TEPA, which is a value higher than the ones obtained with filler. For
ICAs elaborated with commercial Ag flakes, an abrupt decrease in the shear
strength is observed at the beginning and then a slow decrease as a function of
the DTT concentration. An opposite behavior is observed for the ICAs filled
with recycled Ag particles where the shear strength increases abruptly at the
beginning and continues to increase with the increase of the DTT concentration.
For the ICAs with commercial particles, it seems that the lubricant layer
improves the mechanical properties and as soon as the DTT molecules start to
substitute this layer the shear strength reduces. For the Ag recycled particles, the
initial values for 0 and 0.1 mM DTT are relatively low due to the fact that the

Figure 7. Shear strength of ICAs filled with 80 wt % of recycled (circles) or commercial (squares)
Ag particles as a function of DTT concentration. The result for the adhesive without filler (up
triangle) is also shown for comparison.
12 C. S. DE OLIVEIRA ET AL.

particles are still in aggregates, as shown in Figures 3 and 4, and for higher
concentrations of DTT the agglomerates are dissolved and the Ag particles are
better dispersed improving the mechanical properties. The higher values of σ for
ICAs filled with recycled Ag treated in 1 and 10 mM DTT solutions relative to
samples of commercial Ag incubated in solutions with same concentration can
be attributed to the superior dispersion of the particles in the adhesive, due to the
better DTT coverage and smaller size. Moreover, the value of σ for the highest
concentration of DTT of 21 MPa is close to the shear strength of adhesives
formulated without filler.

4. Conclusions
Ag particles obtained commercially or from recycled waste jewelry were used
successfully for the preparation of ICAs. The electrical and mechanical properties
obtained in this work are comparable to existing values in the literature. The
coverage of the surface of the Ag particles with DTT improved significantly
the electrical resistivity of the ICAs. The particles from recycled Ag enhanced the
electrical and mechanical properties of the ICAs as a function of the concentration
of DTT in the incubation solution. The better results were for recycled particles
when compared to commercial ones and were attributed to the smaller size and
better DTT coverage due to the absence of lubricant coating of recycled Ag.

Acknowledgements
The authors wish to thank the LCME for the electron microscopy facilities, Prof. R. A. F.
Machado (LCP/UFSC) for the contact angle measurements, and LABMAT/UFSC for com-
plementary shear strength tests.

Funding
This research was supported by Brazilian agencies CAPES, CNPQ, FINEP, and FAPESC.

ORCID
Silvio de Barros http://orcid.org/0000-0002-2520-569X

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