Single-Chain Folding Nanoparticles as Carbon Nanotube Catchers

Article abstract of DOI:10.1002/pola.29245

This contribution describes a simple method for preparing polymeric nanoparticles using photodimerization of anthracene moieties on the side chain of terpolymers in dilute regime and transformation of obtained polymeric nanoparticles into pyrene functional nanoparticles via Menschutkin quaternization procedure. Subsequently, pyrene possessing polymeric nanoparticles are attached onto multiwalled carbon nanotube (MWCNT) surfaces by π–π stacking strategy. Gel permeation chromatography, thermal gravimetric analysis, ultraviolet–visible, and fluorescence spectroscopies are used to analyze modified nanoparticles and their precursors. Electron microscopy and dispersion studies show that pyrene-modified polymeric nanoparticles are able to interconnect various CNTs.

Full text of DOI:10.1002/pola.29245

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Single-Chain Folding Nanoparticles as Carbon Nanotube Catchers
3
Mesut Bilgi,1 Demet Karaca Balta,1 Binnur Aydogan Temel ,2 Gokhan Temel
1Department of Chemistry, Yildiz Technical University, Istanbul 34220, Turkey
2Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Bezmialem Vakif University, Fatih, Istanbul 34093, Turkey
3Department of Polymer Engineering, Faculty of Engineering,Yalova University, Yalova 77200, Turkey
Correspondence to: G. Temel (E-mail: gtemel@yalova.edu.tr)
Received 26 June 2018; Accepted 10 September 2018
DOI: 10.1002/pola.29245
ABSTRACT: This contribution describes a simple method for pre-
paring polymeric nanoparticles using photodimerization of
anthracene moieties on the side chain of terpolymers in dilute
regime and transformation of obtained polymeric nanoparti-
cles into pyrene functional nanoparticles via Menschutkin qua-
ternization procedure. Subsequently, pyrene possessing
polymeric nanoparticles are attached onto multiwalled carbon
nanotube (MWCNT) surfaces by π–π stacking strategy. Gel
permeation chromatography, thermal gravimetric analysis,
ultraviolet–visible, and fluorescence spectroscopies are used to
analyze modified nanoparticles and their precursors. Electron
microscopy and dispersion studies show that pyrene-modified
polymeric nanoparticles are able to interconnect various CNTs.
© 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym.
Chem. 2018
KEYWORDS: carbon nanotube; hybrid materials; photodimeriza-
tion; polymeric nanoparticles
density, electrical and thermal conductivity, high aspect ratio,
chemical stability under harsh conditions, and nanocomposite
component.24 In order to overcome these disadvantages,
noncovalent and covalent functionalization methodologies
were addressed in various publications and modified CNTs
were successfully achieved with improved dispersion
properties.24–30 Noncovalent route is extensively applied to
obtain modified nanostructures such as π–π stacking interac-
tions between CNT walls and polynuclear aromatic group con-
taining polymers. The use of noncovalent technique is an
efficient way to achieve functional CNTs without alteration of
their intrinsic behaviors such as molecular conjugation, opti-
cal, and thermal properties.31–34
INTRODUCTION The development of the intramolecular chain
folding has been a field of polymer science and technology
because of its crucial potential applications on CO2 capturing,1
production of catalysis,2–4 drug delivery,5 and responsive
polymeric materials.6–8 Chain folding process is one of the
most unique and reliable method to produce functional mac-
romolecular nanoparticles. Linear precursor undergoes intra-
molecular chemical interactions in dilute condition and
transforms into the folded-chain structure. Resulting poly-
meric nanostructure becomes a more compact particle and
generally it is smaller than its previous size. Crosslinkable
species can be located on the side chains of the linear precur-
sor by varying chemical techniques or added externally to the
reaction environment in order to synthesize polymeric
nanoparticles.9–11 Therefore, several synthetic strategies have
been carried out to achieve nanosized materials such as
photodimerization,12–14 stepwise folding,15 benzocyclobutene
chemistry,16 and atom transfer radical coupling.17,18
In order to obtain the benefits of both polymeric nanoparticle
and CNT, we decorated surface of CNT with single-chain fold-
ing polymeric nanoparticles (SCNPs) via noncovalent interac-
tions strategy. First, amine and anthracene containing
terpolymer was readily synthesized by radical polymerization
technique. Afterward, polymeric nanoparticles were achieved
by dimerization of anthracene moieties on the side chain of
the terpolymers in dilute medium and pyrene functional nano-
particles were achieved via straightforward Menschutkin qua-
ternization procedure using tertiary amine functionalities of
nanoparticles and 1-(bromoacetyl)pyrene. Finally, pyrene pos-
sessing polymeric nanoparticles were attached onto
After discovery of carbon nanotubes (CNTs) in 1991, polymer
science has found a new pathway for nanotechnology applica-
tions like drug delivery systems,19 microelectronics,20,21
energy storage,22 and biotechnology.23 Although CNTs have
major drawbacks such as self-aggregation, lack of solubility in
conventional solvents and low dispersion behavior in polymer
matrix due to the strong van der Waals forces between parti-
cles, they include powerful properties such as low mass
Additional supporting information may be found in the online version of this article.
© 2018 Wiley Periodicals, Inc.
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multiwalled carbon nanotube (MWCNT) surfaces using π–π
stacking interactions.
7.5 mmol) dissolved in THF (1.5 mL) was added dropwise to
a solution of 9-anthracenemethanol (1.04 g, 5 mmol) and
triethylamine (0.7 mL, 5 mmol) in the mixture of THF
(20 mL) at 0 ꢀC under nitrogen atmosphere. After the addition
of methacryloyl chloride solution, the resulting mixture was
stirred at room temperature overnight in the dark. After addi-
tion of 30 mL dichloromethane, the mixture was washed with
excess water and saturated aqueous solution of NaHCO3
(200 mL). To neutralize the organic phase, extraction was car-
ried out with saturated aqueous solution of NaCl (200 mL).
The organic layers were dried over anhydrous Na2SO4, fil-
tered, and then the solvent was evaporated. The resulting resi-
due was purified by recrystallization from methanol. Yield:
65%. Gas chromatography–mass spectrometry (electron
impact, 70 eV): 276 (M+) (Fig. S1).
EXPERIMENTAL
Materials
α,α0-Azoisobutyronitrile (AIBN, 98%) was purchased from
Aldrich (Germany) and recrystallized from ethanol. MWCNT Bay-
tubes C 150 P (Bayer, Germany), N,N-dimethylformamide (DMF,
Merck, Germany), methanol (Merck, Germany), n-hexane (Merck,
Germany), 1-(bromoacetyl)pyrene (Aldrich, 97%, Germany),
9-anthracenemethanol (Aldrich, 97%, Germany), tetrahydrofuran
(THF, Sigma-Aldrich, 99.9%, contains BHT as inhibitor, Germany),
and methacryloyl chloride (97%, contains ~200 ppm mono-
methyl ether hydroquinone as stabilizer, Aldrich, Germany)
were used as received. Methyl methacrylate (MMA, Aldrich, 99%,
Germany) and 2-(diethylamino)ethyl methacrylate (contains
1500 ppm MEHQ as inhibitor, DEAEMA, Aldrich, 99%, Germany)
were deinhibited by passing over basic alumina. All other
reagents were used as received.
Synthesis of Poly(DEAEMA-co-MMA-co-AntMac)
Poly(DEAEMA-co-MMA-co-AntMac) (PDMA) was prepared by
free-radical polymerization (FRP) in the presence of AIBN
under nitrogen atmosphere. To a flask equipped with a mag-
netic stirring bar, 0.5 mL of DMF, MMA (0.432 mL, 4.06 mmol),
DEAEMA (0.153 mL, 0.75 mmol), AntMac (0.07 g, 0.25 mmol),
and AIBN (0.0147 g, 0.09 mmol) were added in that order.
After short nitrogen bubbling, the reaction flask was placed in
a thermostated oil bath for 24 h at 85 ꢀC. At the end of the
period, solvent was evaporated and the resulting product was
precipitated two times using THF as a good solvent and cold
n-hexane as a poor solvent. Polymeric product was filtered
and dried for 24 h at room temperature. Yield: 72%.
Instrumentation
A merry-go-round type photoreactor (Kerman) equipped with
18 Philips 8W lamps emitting light nominally at λ = 350 nm
was used. Ultraviolet (UV) spectra were recorded on Hitachi
U-2900. Fluorescence emission spectra were recorded on
Hitachi F-2700 spectrophotometer. Proton nuclear magnetic
resonance (1H NMR) spectra were performed on a Bruker
Avance Spectrometer (500 MHz) using CDCl3 as solvent. Gel
permeation chromatography (GPC) measurements were per-
formed on a Viscotek GPCmax VE 2001 Autosampler system
equipped with Viscotek VE 3580 refractive index
(RI) detector. Three Viscotek GPC columns (T3000, LT4000L,
and LT5000L), (7.8 mm internal diameter, 300 mm length),
and a Viscotek guard column (CLM3008, 4.6 mm internal
diameter, 10 mm length) were used in series. The effective
molecular weight ranges were 456–42,800, 1050–107,000,
and 10,200–2,890,000, respectively. THF was used as an eluent at
a flow rate of 1.0 mL min−1 at 35 ꢀC. Detector was calibrated with
polystyrene (PS) standards having narrow molecular weight dis-
tribution. Data were analyzed using Viscotek OmniSEC 4.7.0 soft-
ware. Particle size distributions were determined using dynamic
light scattering (DLS) in THF dispersions using a Malvern
NanoZSP instrument. Differential scanning calorimetry (DSC) mea-
surements were performed on a TA Instruments DSC-Q200 with
a heating rate of 10 ꢀC min−1 under nitrogen atmosphere. TGA
measurements were carried out with a SEIKO ExStar 6300 instru-
ment under inert atmosphere at a heating rate of 10 ꢀC min−1
Synthesis of SCNP
Total of 150 mg of PDMA was dissolved in 300 mL of THF
and the solution was stirred for 10 min under nitrogen bub-
bling and continued stirring for 120 min at room temperature
under nitrogen atmosphere. Subsequently, solution was irradi-
ated in a photoreactor consisting of 18 lamps at λ(nominally) = 350 nm
for 60 min. At the end of the irradiation period, solvent was
evaporated and product was dried in a vacuum oven at room
temperature.
Modification of SCNP with 1-(Bromoacetyl)pyrene
The Menschutkin reaction of SCNP was carried out with
1-(bromoacetyl)pyrene to synthesize the pyrene functiona-
lized SCNPs in DMF. A typical quaternization was conducted
as follows: SCNP (100 mg) was diluted in 2 mL of DMF. The
mixture of 1-(bromoacetyl)pyrene (80 mg) and 1 mL of DMF
was added dropwise into the prepared polymer solution. Under
continuous stirring for 24 h, solvent was completely evaporated
and solid polymer was dissolved in 3 mL of THF. Resulting poly-
mer was precipitated in 50 mL of cold n-hexane. Solid copolymer
was redissolved in THF and reprecipitated in cold n-hexane to
remove unreacted 1-(bromoacetyl)pyrene. Then, polymer was
filtered and dried in vacuum at 30 ꢀC for 24 h. Yield: 45%.
ꢀ
between 25 and 850 C. The morphology of nanostructures was
analyzed by a high-resolution transmission electron microscope
(HRTEM) JEOL JEM-2100 and samples were prepared by drop
coating a dilute solution of the sample in THF on a holey carbon-
coated copper grid.
Synthesis of Methacrylated Anthracene
Modification of MWCNT with SCNP-Py (SCNP-
Methacrylated anthracene (AntMac) was synthesized accord-
ing to a modified literature procedure.12 Synthetic procedure
was carried out as follows: methacryloyl chloride (0.75 mL,
Py@MWCNT) and SCNP (SCNP@MWCNT)
Total of 40 mg of polymeric nanoparticle (SCNP or SCNP-Py)
was dissolved in a round-bottom flask in 20 mL of THF and
2
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FIGURE 1 GPC traces of terpolymer (solid line) and SCNP (dash
line) recorded with RI detector in THF at 35 ꢀC. [Color figure can
be viewed at wileyonlinelibrary.com]
In order to achieve anthracene and tertiary amine containing
copolymer structure, MMA, 2-(diethylamino)ethyl methacry-
late and AntMac were used in thermally initiated FRP
(Scheme 1). Targeted linear copolymer consists of randomly
distributed three different monomer groups. Side-chain
anthracene moieties were utilized to form intramolecular
crosslinked structure with photodimerization procedure and
tertiary amine functionalities were subsequently quaternized
by 1-(bromoacetyl)pyrene for the attachment onto CNT via
noncovalent interactions (Scheme 1). According to 1H NMR
results of the PDMA, lateral protons of each monomer show
that free-radical copolymerization was successfully performed.
Ester protons (-OCH2) of DEAEMA and AntMac appeared at
4.07 and 6.13 ppm, respectively. In addition, -OCH3 protons of
MMA were detected at 3.65 ppm and DEAEMA/MMA/AntMac
compositions were in good agreement with monomer feed
ratios using calculation of integral area of each segment
(Fig. S2 and Table 1).
SCHEME 1 Overall synthetic mechanism for the SCNP-coated
MWCNT. [Color figure can be viewed at wileyonlinelibrary.com]
It is well known that SCNPs have more compact architectures
and their molecular weight values are generally smaller than
their precursors. Berda and coworkers successfully synthe-
sized sub-20 nm soft nanoparticles using intramolecular
photodimerization of pendant anthracene units.12 According
to the results of their work, high anthracene concentration in
the copolymer causes unavoidable intermolecular crosslinking
reactions. Therefore, we limited the concentration of AntMac
monomer at 5% mol during the synthesis of terpolymer
(PDMA). 1H NMR results revealed that concentration of
anthracene moieties in terpolymer and photodimerization
degree of anthracene moieties in SCNP are 4 and 65%, respec-
tively. After photodimerization process, molecular weight
30 mg CNT was added. The mixture was sonicated for 15 min
in an ultrasonic bath and allowed to stir for 3 days. At the end
of this period, the resulting mixture was filtered and washed
with 80 mL fresh THF through Teflon membrane to eliminate
the unattached polymeric nanoparticles. The final product
was dried in vacuum at 30 ꢀC for 24 h.
RESULTS AND DISCUSSION
In this study, we propose a new perspective to have dense
polymeric coil obtained by folding process through intramo-
lecular photodimerization onto CNT surface.
TABLE 1 Copolymer Compositions, Molecular Weight Results, and Particle Size Comparisons of Terpolymer and Single-Chain
Collapsed Nanoparticle
DEAEMA conc. in copolymerb
Sample (mol %)
AntMac conc. in copolymerb
(mol %)
Mn
Polydispersity
indexc
Rhd
(mm)
c
(g mol−1
)
PDMAa
SCNP
a
14
4
–
d
12395
5360
2.22
1.48
7.4
5.2
–
Feed ratio of DEAEMA/MMA/AntMac = (15/80/5 mol %).
Particle size (nm) determined by DLS for nanoparticle samples sus-
pended in THF.
Calculated by 1H NMR spectra.
Determined by GPC according to linear PS standards.
b
c
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FIGURE 4 Emission spectra of terpolymer, SCNP, and SCNP-Py
in THF (c = 7 × 10−4 mg mL−1, λexc = 345 nm). [Color figure can
be viewed at wileyonlinelibrary.com]
FIGURE 2 DLS measurements of PDMA (black line) and SCNP
(blue line) at 25 ꢀC in THF. [Color figure can be viewed at
wileyonlinelibrary.com]
Thermal properties of terpolymer and SCNP were also investi-
gated by DSC analyses. Intramolecular crosslinked nanoparti-
cles (SCNP) have higher Tg value compared to linear
copolymer precursor. Reduced chain mobility of the nanopar-
ticle resulted by intramolecular photodimerization causes a
significant increase in glass transition temperature (Tg) which
value of collapsed particle is quite different comparing to its
noncrosslinked precursor as excepted (Table 1 and Fig. 1).
In addition, hydrodynamic radius of resulting nanoparticle
decreases because obtained nanoparticle has much more com-
pact size than its linear precursor (Fig. 2 and Table 1).
ꢀ
shifts from 98.71 to 130.52 C (Fig. 5). Also, it was previously
reported that heating the dimer product between 160 and
As can be seen from both UV–visible (UV–vis) and fluores-
cence spectra, after light-induced dimerization of anthracene
moieties, absorption, and fluorescence intensity values
decrease (Figs. 3 and 4). Besides, pyrene-modified SCNP sam-
ple exhibit very high intensity in emission spectra between
365 and 600 nm due to the high quantum yield of pyrene
moieties (Fig. 4). Moreover, side-chain anthracene functionali-
ties still exist in the SCNP and they are easily detectable by
spectral analyses.
ꢀ
200 C temperatures causes to scission into its corresponding
anthracene moieties.35,36 Therefore, we did not exceed 160 C
ꢀ
during analyses in order to avoid scission of dimerized junc-
tion points along the copolymer structure.
In order to gain more insight into thermal behavior of nano-
particle decorated MWCNT and pyrene analogue of SCNP,
TGAs were carried out as well (Fig. 6). Pyrene-modified
FIGURE 3 Absorption spectra of terpolymer, SCNP, and SCNP-
Py in THF (c = 2 × 10−1 mg mL−1). [Color figure can be viewed at
wileyonlinelibrary.com]
FIGURE
5
DSC thermograms (second heating scan) of
terpolymer and SCNP. [Color figure can be viewed at
wileyonlinelibrary.com]
4
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to TGA results. These results show that pyrene existence in
the nanoparticle architecture increases grafting ratio of SCNP
onto MWCNT’s surfaces as expected. On the other hand, due
to the existence of bare anthracene units on folded nanoparti-
cles, noncovalent interactions between anthracene groups and
MWCNT’s surface increase grafting ratio.
SCNP-Py@MWCNT samples in different solvents were demon-
strated in Figure 7 to determine the dispersion properties.
After sonication, samples exhibit poor dispersion behavior in
acetone and DMF in 15 min. Even though THF shows better
solubility than DMF and acetone, particle aggregation was
detected after 1 h. This particle association was ascribed to
increase interconnection tendency of CNT particles by pyrene
functionalized folding nanoparticles.
Although DLS measurement of SCNP emphasizes sub-10 nm
particle size, TEM pictures demonstrate that polymeric nano-
particles tend to be larger globular shape due to the chain
aggregation (Fig. S3). This trend can be explained by solvent
evaporation after casting on a copper grid; therefore, particles
seem to incline to association during drying. TEM photographs
of SCNP-Py-modified CNTs exhibit large aggregation behavior
and this manner may be attributed to high interaction capabil-
ity of SCNPs possessing pyrene groups with different MWCNT
surfaces [Fig. 8(A)]. In higher magnifications, sub-10 nm sized
globular shaped polymeric nanoparticles are obviously seen
on CNT particles and this attitude makes pyrene containing
SCNPs potential crossing points for CNT particles [Fig. 8(B,C)].
FIGURE
6 Thermogravimetric analyses of SCNP-Py, SCNP-
Py@MWCNT, and SCNP@MWCNT. [Color figure can be viewed
at wileyonlinelibrary.com]
CONCLUSIONS
In conclusion, we have demonstrated the decoration of poly-
meric nanoparticles onto CNT surface via noncovalent interac-
tions. Polymeric nanoparticles have been produced by
photodimerization process of anthracene species on the side
chain of the linear terpolymer. GPC, DLS, and TEM results
revealed that single-chain polymeric nanoparticles were suc-
cessfully synthesized. Next, pyrene moieties were incorpo-
rated into the tertiary amine pendant groups of polymeric
nanostructure using straightforward quaternization reaction.
According to UV–vis and fluorescence spectra, SCNP produc-
tion and its pyrene functionalization were successfully carried
out. Pyrene containing SCNPs were grafted onto MWCNT side
walls by π–π stacking strategy. Incorporated pyrene units
were strongly interacted with MWCNT surfaces as was evi-
denced by TGA results and electron microscopy studies. Elec-
tron microscopy images showed polymeric particles
FIGURE 7 Durability images of SCNP-Py@MWCNT in different
solvents. [Color figure can be viewed at wileyonlinelibrary.com]
polymeric nanoparticle has a char yield (12%) because of
ionic moieties and rigid dangling pyrene groups in the struc-
ture. MWCNT was also modified with SCNPs in order to com-
pare grafting ratios of SCNP and SCNP-Py. While SCNP-Py
coated MWCNT sample shows 18% grafting ratio,
SCNP@MWCNT sample has 14% polymer content according
FIGURE 8 HRTEM images of SCNP-Py@MWCNT.
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CNT particles in organic solvents can be collected by SCNPs
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