GENERATION OF MOLECULARLY IMPRINTED ELECTROSPUN … · GENERATION OF MOLECULARLY IMPRINTED...

European International Journal of Science and Technology Vol. 5 No. 9 December 2016

47

GENERATION OF MOLECULARLY IMPRINTED ELECTROSPUN

NANOFIBERS FOR ADSORPTION OF 4-NITROPHENOL WITH

QUARTZ CRYSTAL MICROBALANCE METHOD

Sibel Emir Diltemiz 1*

and RabiaBerna Demirel 2

1,2 Department of Chemistry, Anadolu University University, Eskişehir, Turkey

*Correspondence Author:

Sibel Emir Diltemiz

Anadolu Üniversitesi, Fen Fakültesi, KimyaBölümü,

YunusEmreKampüsü, 26470 Eskişehir, Turkey

E-mail : [email protected]

ABSTRACT

In this study, it has targeted determination of 4-Nitrophenol (4-NP), which is a toxic and carcinogenic

compound at high selectivity. For this purpose, firstly molecularly imprinted nanoparticles was synthesis by

mini-emulsion polymerization by using 4-NF as template. Then nanofiber systems containing 4-NP

imprinted nanoparticles have been developed by electro spinning technology. 4-NP imprinted nanoparticles

containing nanofiber systems is coated onto Quartz Crystal Microbalance (QCM) electrode. The electrode

was used for determination of 4-NF from aqueous solution. Scatchard, Langmuir, Freundlich and Temkin

adsorption models were applied to describe the adsorption isotherms.

Keywords: 4-Nitrophenol, QuartzCrystalMicrobalance, MolecularlyImprintedPolymers, Electrospinning

1. INTRODUCTION

Polymer based nanomaterials, due to their chemical and mechanical properties can be used in a number of

different applications such as adsorption of various metal and organic chemicals [1], catalyst (Günter Wulff,

2011), chromatography (Svec & Kurganov, 2008), development of sensors and electrodes (Chen, Wen, &

Teng, 2003). Also polymeric nanomaterials offer a wide opportunity of modulating their adsorption capacity

through the control of both morphology and chemical composition (Kang, Chen, Zhang, Liu, & Gu, 2008;

Khajeh, Laurent, & Dastafkan, 2013) Among the different synthetic strategies, molecular imprinting is

probably the most straightforward for the purpose of producing nano and micro structured materials that

have predesigned molecular recognition capabilities(Conrad et al., 2003; H. C. Huang, Lin, Joseph, & Lee,

2004; Yang et al., 2004)

mailto:[email protected]

European International Journal of Science and Technology ISSN: 2304-9693 www.eijst.org.uk

48

The technique of molecular imprinting creates specific molecular recognition sites in solid materials by

using template molecules. In this process, a complex of a functional monomer with a template is

copolymerized with a cross-linking agent and removal of the template from the polymerized matrix

generates the binding sites that are compatible to the template (Kim & Chang, 2011). Three different

methods to prepare MIPs have been reported, depending on the bond that is established between the

template molecule and the polymer (covalent, noncovalent, and semicovalent approaches) are reported

(Turiel & Martín-Esteban, 2010). A noncovalent approach has been used in this work, because relatively

weak noncovalent intermolecular interactions, between the template molecule 4-NPand the functional

monomers served to form the molecular assemblies. To use MIPs in applications such as sensing or affinity

separation, it is often required to immobilize the polymer onto solid surfaces. Several research studies have

been carried out by combining the amazing properties of MIPs and nanofibers to obtain molecularly

imprinted polymer nanofibers (MIP-NFs)(Zaidi, 2015)(Li, 2012). Furthermore, nanofiber sorbents not only

possesses a great specific surface area, which allows a more efficient adsorption, but also the possibility to

remove them by solution more easily(Piperno, Tse, Bui, Haupt, & Gheber, 2011).

The electrospinning process produces continuous polymer nanofibers with diameters ranging from a few

nanometers to several micrometers (usually between 50 and 500 nm) through the action of an external

electric field imposed on a polymer solution or melt(Chronakis, Milosevic, Frenot, & Ye, 2006; Z.-M.

Huang, Zhang, Kotaki, & Ramakrishna, 2003; Subbiah, Bhat, Tock, Parameswaran, & Ramkumar, 2005).

Electrospun nanofibers have very high surface area, mechanical strength, and flexibility. When collected on

a plain target plate, they can easily form defined three-dimensional mats with well-controlled pore sizes.

This makes electrospun nanofiber matsideal candidates for industrial filtration purposes. It is highly

desirable for selective molecular recognition sites to be able to be introduced into nanofiber materials as

they may provide highly efficient compound separation involving only a simple filtration step(Gibson,

Schreuder-Gibson, & Rivin, 2001). In this study, we report on the entrapping of MIP nanoparticles in

electrospun polymer nanofibers, thus creating a nonwoven mat of sensing sites with a high surface area and

accessibility.

2. EXPERIMENTAL

2.1. Materials

4-NP, methacrylic acid (MAA), Ethylene glycol dimethacrylate (EDMA), hexadecane, 2,2'-azobis(2-

methylpropionitrile) (AIBN), polyvinyl alcohol (PVA, MN ~ 72.000), potassium bromide (FTIR grade) and

sodium dodecyl sulphate (SDS) were supplied by SIGMA-ALDRICH (Milwaukee, WI, USA). All

glassware was extensively washed with diluted HNO3 before use. All other chemicals were of analytical

grade purity and purchased from Merck AG (Darmstadt, Germany). All water used in the experiments was

purified using a Barnstead (Dubuque, IA) ROpure LP® reverse osmosis unit with a high flow cellulose

acetate membrane (Barnstead D2731) followed by a Barnstead D3804 NANO pure® organic/colloid

removal and ion exchange packed-bed system.

2.2. Apparatus

House-made electrospun system was built and used for fiber production. A custom-made high voltage DC

converter (EMCO 4300) was biased with a DC power supply. FTIR spectroscopy was used in the 4000-400

cm-1 range for the characterization of functional monomer, pre-organized complex, and imprinted beads in

the solid state (FTIR 100 series, Perkin Elmer, USA). The size of the particles was determined by dynamic

light scattering on a Malvern Instruments Zeta Sizer. The imprinted beads and nanofibers were characterized


49

by field emission gun scanning electron microscope (FESEM, ZEISS Ultraplus), SONOPULS HD 2070,

BANDELIN, (Germany) model homogenizer and MPW-251, MPW Med-Instruments (Poland) centrifuge

were used for homogenization and centrifuge processes.

2.3. Synthesis of 4-NP imprinted nanoparticles

MIP nanoparticles were prepared with mini emulsion polymerization method which used by Belmont et. al.

(Belmont et al., 2007). Therefore, the organic phase that contained 1.72 mmol of MAA, 6.9 mmol of

EDMA, 80 μL of hexadecane and 30 mg of AIBN was prepared and then ultrasonicated for 1 min. The

aqueous phase was prepared by dissolving of 0.5 mmol4-NP and 38.5 mg of SDS in 18 mL of water. The

organic phase was slowly added to the aqueous phase. In order to obtain mini-emulsion, the mixture was

homogenized at 25.000 rpm by a homogenizer (SONOPULS HD 2070, BANDELIN, Germany). Polymer

mixture was stirred and held in 70ºC water bath for 18 hours to obtain nanoparticles. The 4-Np imprinted

nanoparticles were washed three times 5h against water and water/ ethylalcohol mixtures in order to remove

unreacted monomers, surfac tantand initiator. To removing imprinted molecule, the mixture was washed

with methanol: acetic acid (4:1) solution three times for two hours.

FT-IR, Zeta-sizer and SEM analyzes were performed to nanoparticles characterization. Particle size was

measured by Malvern Instrument Zeta-sizer device. 30µg/ml water suspension was prepared for this

purpose. The imprinted 4-NP and nonimprinted MIP nanoparticles were examined and imaged by Scanning

Electron Microscope.4-NPimprinted and nonimprinted MIP nanoparticles were mixed with 98 mg

potassium bromide and grounded until turn into fine powder form then pressed to pellet for FTIR

measurement.

2.4. The coating of QCM sensors with 4-NP imprinted polymer encapsulated nanofibers and their

characterization.

Chronakis et al.’s method was used for preparation of 4-NP imprinted polymer encapsulated nanofibers

(Yoshimatsu, Ye, Lindberg, & Chronakis, 2008). 3 ml Dichloromethane (DCM), 3 ml trifluoroacetic acid

(TFA) were mixed then 0,5 gr poly ethylene terephthalate (PET), 0,05 gr polyvinyl alcohol (PVA), NaCl

were added to this mixture and stirred for two hours.The prepared mixture was filled in plastic syringe and

placed to syringe pump (KDS-200, Focus Co., Ltd., USA) for electrospinning. The positive side of the high

voltage power supply was attached to the syringe’s 0,8 mm diameter metal needle tip. The solution feeding

rate was adjusted to 1,5 mL/h. Gold coated quartz crystals were used as collector electrode and placed

horizontally which has a 130 mm distance away from the needle tip. Before electrospinning, the QCM

crystal surface was cleaned in piranha solution (H2SO4/30% H2O2 (3:1, v/v)) for 5 min, rinsed thoroughly

with Milli-Q water, and dried with a stream of nitrogengas. The quartz portion of the QCM electrode was

covered with aluminum folio to prevent unwanted interaction with nanofibers. System voltage was adjusted

as 10kV in room temperature. The fibers were deposited on the quartz crystal (Figure 2.1a) and left to dry

after deposition to remove trace amount of solvent. 4-NP nonimprinted polymer encapsulated nanofibers

preparation steps were remained same. For this purpose 4-NP nonimprinted particles were added to the

PET-PVA mixture and stirred for one hour to obtain homogenous mixture. The same parameters and

conditions were applied during electrospinning.


50

(a)

(b)

Figure 2.1.(a) Theschematicview of nanofibercreation on QCM electrodewithelectrospinningprocessand (b)

formation of Taylor cone

2.5. The sensor measurements of nanofibers coated QCM electrode

The QCM sensors consist of a disk-shaped, AT-cut piezoelectric quartz crystal, coated with gold thin layer

on both sides and operate at a frequency of 5 MHz. The resonance frequencies were measured by using a

QCM digital controller (MAXTEK RQCM, Research Quartz Crystal Microbalance Monitor). For this

purpose electrode was attached to the holder, rinsed with water via perilstatic pump at room temperature for

stabilization then measured constant resonance frequency (F0).0.5 ppm 4-NP solution was passed on

electrode and sensor frequency observed until stable value (F1) The frequency shift of all 4-NP

concentrations (0.5-100 ppm were calculated from ΔF=F0–F1 equation. The electrodes were rinsed with

H2O and 0.1 mMglisin/10 mMHCl mixture until sensor frequency come close to F0 value to remove

template after every concentration measurement step. The binding value of nano sensor to 4-NP molecules

is statistically calculated from three values of blank solution.


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Figure 2.2. QCM measurement with 4-NP imprinted polymer encapsulated nanofibers coated QCM sensor

3. RESULTS

3.1. 4-NP imprinted nanoparticles characterization

4-NP imprinted nanoparticles were prepared by two-phase emulsion polymerization method. In this

technique, polymerization process performed by passing from stabile oily phase to water phase. The FTIR

characterization of 4-NP imprinted and nonimprinted polymers were carried out by FTIR spectrometer. The

dried polymer mixed with KBr and shaped to tablet form to obtain FTIR spectrum. The FTIR spectrum of 4-

NP imprinted and nonimprinted polymers can be shown in Figure 3.1A.As seen from FTIR spectra specific

bands of the polymeric structure have been detected. In the FTIR spectrum characteristic peaks of 4-NP

imprinted nanoparticles are carboxylic acid O-H band at 3568 cm-1

, C-H stretching at 2980 cm-1

and

carbonyl peak (C=O) at 1728 cm-1

. When FTIR spectrums of imprinted and nonimprinted polymers are

compared, the peak is observed at 1637 cm-1

in 4-NP imprinted polymers. It is believed that this peak should

be come from benzene ring’s C=C bending band. For Zeta-Sizer measurements 4-NP imprinted

nanoparticles were suspended in deionized water with 30 µg/ml ratio to measure particle size. Zeta-Sizer is

benefit from light scattering techniques and is capable of hydrodynamic sizing of nanoparticles, determining

of zeta potential and molecular weight. Zeta sizer analysis result can be shown in Figure 3.1B. The obtained

nanoparticles size is found about 200 nm. 4-NP imprinted nanoparticle’s size and morphology were revealed

with SEM analysis. Nanoparticles were dried and coated with gold before SEM surface analysis. SEM view

of 4-NP imprinted nanoparticles is given in Figure 3.1C.

(a) (b)

(A)

NIP B.Csız_1

Name

Sample 493 By Analyst Date Friday, July 29 2016

Description

4000 4003500 3000 2500 2000 1500 1000 500

89

58

60

62

64

66

68

70

72

74

76

78

80

82

84

86

88

cm-1

%T

1728.73cm-1

1159.51cm-1

1263.65cm-1

1452.68cm-1

2987.92cm-1

1389.32cm-1

954.89cm-1

3568.59cm-1

4NF-MIP_1

Name

Sample 495 By Analyst Date Friday, July 29 2016

Description

4000 4003500 3000 2500 2000 1500 1000 500

105

25

30

40

50

60

70

80

90

100

cm-1

%T

1728.68cm-1

1159.80cm-1

1260.40cm-1

2959.07cm-1

1453.86cm-1

1047.47cm-13518.35cm-1

1389.37cm-1

958.01cm-1

1637.23cm-1

879.35cm-1

752.53cm-1

520.32cm-1


52

(B)

(C)

Figure 3.1.(A) The FTIR spectrum of 4-NP imprinted (a) and nonimprinted polymers

(B) Zeta-Size analysis result of 4-NP imprinted nanoparticles

(C) SEM photograph of 4-NP imprinted nanoparticles

3.2. 4-NP imprinted nanoparticle encapsulated nanofibers characterization

4-NP imprinted nanoparticle encapsulated nanofiber’s surfaces were also characterized with SEM. 4-NP

imprinted nanoparticle encapsulated nanofibers were dried, coated with gold before SEM images were

taken. The SEM view of nanofibers that were not containing 4-NP imprintedp articles can be shown in

Figure 3.2- a. 1 mg 4-NP imprinted nanoparticles were added into the polymer mixture and nanofiber

creation process was repeated. The obtained nanofiber’s SEM view is given in Figure 3.2-b.

(a)


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(b)

Figure 3.2. SEM images of nanofibers (a) PET/PVA (b) 4-Nitrophenol imprinted nanoparticle/PET/PVA

3.3.4-NP imprinted polymer encapsulated nanoparticle coated QCM sensor’s binding interactions.

When target molecules bind to the 4-NP imprinted nanofibers, the crystal’s mass changes (Δm) that effects

to frequency. The relation between Δm and frequency shift (ΔF) is expressed with following equation.

∆𝐹 = 𝐶𝑥∆𝑚

Where,

ΔF : frequency shift

Δm: the amount of matter that binds on quartz

C: 56,6 Hzcm2 µg

-1 for 5 mHz crystal

The 4-NP imprinted polymer is expected to bind the 4-NP sensing. The frequency of the sensor increased

after pumping the 4-NP solution. These frequency changes strongly indicated that the 4-NP molecules were

bounded to the imprinted polymer on the quartz crystal.4-NP solutions with different concentration between

0.5 to 100 ppm were pumped to 4-NP imprinted electrode (Figure 3.3). LOD and LOQ values were

calculated as 0,395 nM and 1,2 mM respectively.

Figure 3.3.Change in ΔF and time of 4-NP imprintedparticleencapsulatednanofibercoated sensor

-0.003

-0.002

-0.001

0

0 20 40 60 80 100

Df

(Hz)

Zaman (dk)


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The binding interactions between imprinted nanofibers and 4-NP template is obtained from Scatchard

analysis method. Following equation is used in Scatchard analysis method (Atay, 2016).

∆𝑚

[∁]= −

∆𝑚

𝐾𝐷+∆𝑚𝑚𝑎𝑥

𝐾𝐷

Where,

Δm: The amount of matter that binds on quartz,

C: Free 4-NP concentration

KD : Equilibrium constant in reverse direction

Δmmax: Maximum mass increasing in QCM sensor unit area

Figure 3.4.4-NP imprinted particle encapsulated nanofiber coated QCM sensor’s Scatchardcurve

∆𝑚

∁= −2 × 106∆𝑚 + 11,76

Using with this equation, the binding constant and number of ligand changing sites are found as (KA) 2x106

M-1

and Qmax 11,76 respectively. The founded KA value indicates the binding site’s has strong affinity. KA

value of 4-NP imprinted QCM sensor proves that the developed system is nearly as selective as biological

sensors (Diltemiz, 2010), (Amanda, 2004).

The binding interactions-equations between imprinted polymer encapsulated nanofibers and 4-NP are also

examined with Langmuir, Freundlich and Temkin analysis method.

4-NP imprinted polymer’s Langmuir curve is obtained by following equation and KL and Δmmax values are

found from equation as 2,33x105 M and 5,8x10

-5 respectively. The founded KL value indicates the binding

site’s has strong affinity to target molecule 4-NP.

∆𝑚 =∆𝑚𝑚𝑎𝑥 𝑥 𝐶

𝐾𝐿+ 𝐶

In this equation;

KL: Langmuir constant for a homogeny adsorbent

C: 4-NP free concentration

Δmmax: Maximum mass increasing in unit area of QCM sensor

Δm: Mass increasing amount in unit area of QCM sensor

y = -2E+06x + 11.76R² = 0.946

0

0.5

1

1.5

2

4.80E-06 5.20E-06 5.60E-06 6.00E-06

Δm

(µ

g)

/ C

(M

)

Δm (µg)


55

Figure 3.5.4-NP imprinted polymer’s Langmuir curve

4-NP imprinted polymer’s Freundlich curve is plotted from following equation (Atay, 2016).KF and n

values are found from equation as 5,39x10-12

M and 66,6 respectively.

ℓ𝓃∆𝑚 =1

𝑛ℓ𝓃𝐶 + ℓ𝓃𝐾𝐹

Where,

KF Freundlich constant for heterogenic adsorbent

C: 4-NP free concentration

Δm: Mass increasing amount in unit area of QCM sensor

n: Relation between adsorption force magnitude and energy distribution of adsorbent area

162000

171000

180000

189000

198000

0.00E+00 9.00E+04 1.80E+05 2.70E+05 3.60E+05

1/

Δm

(µ

g)

1/C (M)

y = 0,074x + 17271R² = 0,988

y = 0,219x + 16996R² = 0,684


56

Figure 3.6.4-NP imprinted polymer’s Freundlich curve

4-NP imprinted polymer’s Temkin curve is obtained by following equation

∆𝑚 = 𝐵ℓ𝑛𝐾𝑇 + 𝐵ℓ𝑛𝐶𝑒

Where,

KT : Binding constant of Temkinizoterm (L/gr)

Ce :4-NP free concentration

Δm : Mass increasing amount in unit area of QCM sensor

B : Adsorption constant related with heat (J/mol)

Figure 3.7.4-NP imprinted polymer’s Temkin curve

-12.24

-12.15

-12.06

-11.97

0 2 4 6 8

ln Δ

m

ln C (mM)

y = 0,039x - 12,20R² = 0,852

y = 0,015x - 12,13R² = 0,894


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Table 3.1. The comparison of 4-NP imprinted QCM sensor’s Langmuir, Freundlich and Temkin analysis.

Scatchard Langmuir Freundlich Temkin

R2 0,946 R

2 0,988 R

2 0,894 R

2 0,95

KD 5x10-7

Δmmax 5,80x10-5

1/n 0,015 B 8x10-8

KA 2x106 KL 2,33x10

5 KF 5,39x10

-12 KT 1,4x10

27

CONCLUSION

4-NP imprinted polymer encapsulated nanofibers were created firstly to remove 4-NP in this study.PVA and

PET polymers that are capable of water bending are used in this stage. As can be understood from SEM

images nanofibers are created in randomly distributed, uniform morphology and dense forms. Accessibility

to target molecule and appearance of large part of the nanoparticle surface is accomplished by trapping of

MIP particles with larger diameter than PET/PVA fibers to the fiber interspaces. The binding amount of 4-

NP imprinted nanofibers to 4-NP molecule, calculated from 3 statistical data of blank solution. LOD and

LOQ values are found as 0,027 ppm and 0,081 ppm respectively.QCM nanosensor is developed to

determining 4-NP with high selectivity. 4-NP imprinted nanoparticles encapsulated nanofibers are coated on

QCM electrode. The binding interactions between 4-NP imprinted polymer encapsulated nanofibers and 4-

NP are examined with Scatchard, Langmuir, Freundlich and Temkin analysis methods. The binding constant

(KA) for binding 4-NP molecules to 4-NP imprinted particle-encapsulated nanofibers coated QCM sensor is

found as 2x106 M

-1. This value indicates that the binding sites have strong affinity. Linear character of

plotted curve shows that adsorption process is more suitable to matched with Langmuir. Moreover when

comparing Langmuir, Freundlich and Temkin curves, Langmuir curve has highest correlation coefficient.

This situation indicates single layer and homogeny adsorption exists on QCM sensor. The binding amount

of nanosensor to 4-NP molecule, calculated from 3 statistical data of blank solution. LOD and LOQ values

are found as 0,395 nm and 1,2 mM respectively. The calculated values of observability and determinity

limits are given in table 5.1. The writers of this study couldn’t find a study about determining of 4-NP using

with QCM in literature. Therefore 4-NP determining with using QCM technique could be accomplished

firstly reported in literature with this study.

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