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Abo-Alhasan et al., J Nanomater Mol Nanotechnol 2014, 3:2http://dx.doi.org/10.4172/2324-8777.1000142

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Journal of Nanomaterials & Molecular Nanotechnology

Rapid Induced Aggregation of Gold Nanoparticles by Diolefinic DyesAhmed A Abo-Alhasan1, Samy A El-Daly1,2, Morad M El-Hendawy3,5, Shahar H El-Khalfy1 and El-Zeiny M Ebeid1,4*

AbstractAggregation kinetics of gold nanoparticles (Au NPs) interaction in the presence of some diolefinic dyes, namely 1,4-bis (β-pyridyl-2-vinyl) benzene (P2VB), 1,4 bis(2-methylstyryl) benzene (MSB) and 2,5 distyrylpyrazine (DSP), were studied in methanol using steady state UV-Vis spectrophotometry and stopped-flow spectrophotometry. All three dyes induced the aggregation of Au NPs, but with different rates. The rate of interaction of P2VB and MSB with Au NPs were in time-scale of milliseconds, 6 ms-1 and 3.25 ms-1, respectively, while the interaction between DSP and Au NPs occurred in time-scale of minutes. The rates of interaction between Au NPs and these dyes go in the order of P2VB > MSB » DSP. The density functional theory (CAM-B3LYP) predicted that the dye with higher group charge on the terminal moieties possess higher affinity toward the aggregation as it strengthen its electrostatic interactions with the citrate-capped Au NPs.

KeywordsGold nanoparticles; Dye – induced aggregation; Fast kinetic measurements; Diolefinic dyes; DFT

*Corresponding authors: Dr. El-Zeiny M. Ebeid, Chemistry Department, Faculty of Science, Tanta University, Tanta, Egypt, Tel: +2-0403318302; E-mail: drzeiny@yahoo.com

Received: January 22, 2013 Accepted: March 11, 2014 Published: March 15, 2014

moderate interparticle interaction, a -typical significant red-shift and some broadening of the SPR band occurs. For aggregates with strong interparticle in-teraction, new bands appear due to electronic coupling between particles [9].

A series of gold nanoparticle-based colorimetric sensors were investigated involving the formation of interparticle bridging structures composed of analytes and special functional ligands [10]. When analytes were added to a solution, they interact with the functional ligands that adsorbed on the surface of Au NPs, resulting in the assembly of the Au NPs. This led to changing the solution color from red to blue (or purple) even at nanomolar (nM) concentrations of Au NPs [11]. The color changes due to the association of nanoparticles providing the basis for the development of highly selective and sensitive methodology for the sensing of different DNA types [2,12-18], and for the detection of protein–protein interaction [19].

One of the most important applications of functionalized Au NPs aggregates is its ability to detect heavy metal ions [20-25], anions [26-39], and small organic molecules [40-47]. Geddes et al. were demonstrated a competitive colorimetric glucose assay using assemblies of concanavalin A and dextran-functionalized Au NPs [40,41]. Molecularly imprinted polymers with embedded Au NPs were acted as a colorimetric sensor for adrenaline [42]. Au NPs surface functionalized with water-soluble copolymers [poly(N-n-isopropylacrylamide-co-acryloyldiethyletriamine)] were used for the detection of glutathione [43] . Recently, cysteamine-modified AuNPs were employed for the colorimetric detection of melamine [46] and 2, 4, 6-Trinitrotoluene in real world matrices [47].

Studying the nature of interaction between different organic molecules with Au NPs has significant impact on all the above applications, where organic molecules are capable of binding to gold nanoparticles and/or inducing nanoparticle aggregation. H. M. Zakaria et al. investigated the interaction of Au NPs with small molecules and amino acids at variable pH by means of Zeta potential and UV-Vis spectrophotometry [48]. They demonstrated the ability of thiol, amine, and carboxylic acid functional groups to bind to the surface of Au NPs, and how these binding affect colloidal stability. The mechanisms of aggregation of Au NPs, including surface charge reduction and bridging linkers were also reported.

In the present communication, we report the structural effect of some diolefinic dyes on inducing aggregation of gold nanoparticles (Figure 1). This would in turn have some important applications as chemical and/or biological sensors. To achieve this goal, stopped-flow spectrophotometry and stead state spectrophotometry were employed in conjugation with quantum chemical calculations.

Experimental DetailsMaterials

MSB was obtained from Fluka and used as received. However, P2VB was prepared according to the general procedure reported by Hasegawa et al. [49]. P2VB was obtained by refluxing a mixture of 0.38 mole of terphthaldehyde, 0.117 mole of α-picoline and benzoic anhydride as a dehydrating agent for 8 hours. The precipitated greenish-yellow crystalline product was collected and washed with

IntroductionGold nanoparticles (Au NPs) received considerable attentions

in different areas such as chemical and biological sensing, medical diagnostics and therapeutics and biological imaging, as these small particles exhibit strong surface plasmon resonance (SPR) absorption band [1,2]. Surface plasmon resonance of nanoparticles arises from the coupling of conduction electrons of Au NPs with incident electromagnetic waves [3]. The extinction coefficients of the Au NPs are normally very high (108 to 1010 M-1 cm-1) [4]. The SPR band depends on the shape, size and the surrounding medium of the particles [1-8]. The position and the absorbance of SPR band are sensitive to the interparticle distance. Au NPs exhibit distinctive colors according to their surface plasmon resonance. The fascinating optical properties of Au NP make it an ideal color-indicating candidate for signaling molecular recognition events [2]. The spherical Au NPs with interparticle distance higher than the average particle diameter appears red in color. The color is changed to blue when the interparticle distance becomes smaller than the average particle diameter, as result to aggregation [4]. For aggregates with weak or

Citation: Abo-Alhasan AA, El-Daly SA, El-Hendawy MM, El-Khalfy SH, Ebeid EM (2014) Rapid Induced Aggregation of Gold Nanoparticles by Diolefinic Dyes. J Nanomater Mol Nanotechnol 3:2.

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ethanol and ether. The product was recrystallized from xylene. The yield of P2VB was 74.7% and the melting point was 231-232°C. Extensive purification was achieved by recrystallization and column chromatography on silica gel (60-120 mesh) using methylene chloride as eluent. The chromatographed material was then vacuum-sublimed in the dark under vacuum, ca. 10-3 torr, using a rotary pump at 200°C. DSP was prepared using the procedure described by Hasegawa et al. [50]. A solution of 2, 5-dimethylpyrazine (11 mmol) in crude benzaldehyde (10 ml) was refluxed for two days. The colored mixture was poured in 50 ml ethanol and the resulting solid was collected and recrystallized from toluene. The yield was 50 % of DSP as yellow crystals and the melting point was in the range of 218.5-219.7°C, with an all-trans double bond configuration [49,50]. Extensive purification was achieved by column chromatography on silica gel using methylene chloride as eluent. The chromatographed material was then vacuum-sublimed in the dark.

Tetrachlorauric acid (99.9%, HAuCl4.3H2O) was obtained from Sigma-Aldrich. Citrate trisodium salt (95%, C6H5O7Na3.2H2O), hydrochloric and nitric acids were purchased from Fluka. The glassware and magnetic stirring beads were always cleaned prior to use with freshly prepared aqua regia followed by rinsing with double distilled water.

Synthesis of gold nanoparticles (Au NPs)

Approximately 13 nm diameter Au NPs were prepared by the citrate reduction of HAuCl4.3H2O [51,52]. An aqueous solution of HAuCl4.3H2O (1 mM, 100 mL) was brought to a reflux. While stirring 10 mL of a 1% trisodium citrate solution (as nucleating and reducing agent) was added quickly. After the color changed from pale yellow to deep red, the solution was refluxed for an additional 15 min, then left to cool at room temperature. A typical solution of 13 nm diameter gold particles exhibited a characteristic surface plasmon band around 520 nm. The size and monodispersity of the resulting nanoparticles was well documented for this method of synthesis [53]. The mechanism of the successive reduction of [AuCl4]

- ions into metallic Au NPs was reported in the literature [54,55]. Using the electronic absorption spectra of the Au NPs (2.01 nM), one can calculate the extinction coefficient, ε (λ), at λmax = 520 nm as follow:

ε(λ) = (A/C), ℓ = 1 cm; ε(λ) = 0.3302 / (2.01 × 10-9) = 1.6 × 108 M-1cm-1.

This value is comparable with that previously reported in literature [56].

Instruments

The electronic absorption spectra were recorded using Shimadzu UV-3101 PC spectrophotometer. The fast kinetic measurements were recorded on a Hi-Tech stopped-flow spectrophotometer (Model SF-3L, Salisbury, UK). The spectrophotometer was interfaced with a computer to collect data as changes in signal absorbance / or volt vs time. The dye solution was transferred into one syringe and the other syringe was filled with the colloidal nanoparticles solution. The delivery tubes are constructed of Teflon with an internal diameter of 1.6 mm. Each tube is approximately 40 cm long. Equal volumes of each solution were injected automatically to the examination cell. Thus, the concentration of both injected solutions in the cell is assumed to be the half of the initial concentration in the syringe.

Results and Discussion This section demonstrates the experimental and computational

results of the effect of addition diolefinic dyes to the Au NPs to induce the aggregation. Figure 2 shows the TEM image of the prepared Au NPs. It confirms that the nanoscale dimension of the particles with average diameter of about 13 nm. The electronic absorption spectra of the prepared Au NPs with different concentrations (1.14, 2.15 and 4.37 nM) in methanol were recorded to check up their stability as shown in Figure 3. No changes were observed in the absorption maximum or the spectral profile, which in turn confirm the stability of nanoparticles.

The absorption spectra 1×10-5 M P2VB was measured at different time intervals after addition of 4.37 nM Au NPs, cf. Figure 4. There is a dual decrease of the band maxima of P2VB and Au NPs with an

N

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1,4-bis((E)-2-(pyridin-2-yl)vinyl)benzene P2VB

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1,4-bis((E)-2-methylstyryl)benzene

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Figure 1: The molecular structure of the investigated dyes with full and abbreviated names.

Figure 2: TEM micrograph of gold nanoparticles.

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Figure 3: Absorption spectra of 1.14, 2.15 and 4.37 nM Au NPs in methanol.

Citation: Abo-Alhasan AA, El-Daly SA, El-Hendawy MM, El-Khalfy SH, Ebeid EM (2014) Rapid Induced Aggregation of Gold Nanoparticles by Diolefinic Dyes. J Nanomater Mol Nanotechnol 3:2.

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a b

Figure 8: Photographs of (a) 4.37 nM Au NPs. in methanol and (b) 4.37 nM Au NPs after 2 minutes of addition of 1×10-5 M MSB in methanol.

appearance to a new band appearing at 690 nm which is well known for Au NPs aggregates [4,57-59]. The new band decreased with time due to the gradual destruction of colloidal system. Consequently, this led to precipitation of metallic aggregated Au NPs [57]. Visually, the color of the solution changed during a time less than one minute from red to violet, however after about 30 minutes; the color became blue as illustrated in Figure 5.

Because the interaction between P2VB and Au NPs was too fast, the measurements were performed using stopped-flow technique. The stopped-flow spectrophotometer was set up to follow the appearance of the newly produced band at 690 nm as shown in Figure 6. It was observed that the interaction between 1×10-5 M P2VB and 10.93 nM gold nanoparticles started after 45.6 seconds passed and ended at 282.45 seconds. The reaction was assumed to be pseudo first order as the molar concentration of P2VB is much greater than that of gold nanoparticles by a factor of about ten thousand times. The reaction rate constant was 0.00597 s-1 ≅ 6 m s-1 with good correlation coefficient (R2 = 0.9779) confirming our assumption.

Figure 7 shows the absorption spectra of 1×10-5 M MSB after addition of 4.37 nM Au NPs were measured at different time intervals as a result of the growing interaction between MSB and Au NPs. A new band appeared around 650 nm accompanied by a decrease in

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AuNPs alone 1 min 15 min 45 min 75 min 120 min 180 min

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Figure 4: Absorption spectra of 1×10-5 M P2VB in methanol at different time intervals of 1,15, 45, 75, 90, 120 and 180 minutes after addition of 4.37 n M Au NPs. The dash dot curve is the absorption spectrum of 4.37 nM Au NPs in methanol.

a b c

Figure 5: Photographs of (a) 4.37 nM Au NPs in methanol, (b) 4.37 nM Au NPs after 1 minute of addition of 1×10-5 M P2VB in methanol and (c) after about 30 minutes of addition of 1×10-5 M P2VB in methanol.

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Figure 6: A stopped-flow trace showing absorbance change versus time (in seconds) as a result of the interaction between 1×10-5 M P2VB and 10.93 nM gold nanoparticles in methanol (The instrument was set up to follow the newly produced band at 690 nm).

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Figure 7: Absorption spectra of 1×10-5 M MSB in methanol at different time intervals of 2, 60 and 90 minutes after addition of 4.37 nM Au NPs. The dash dot curve is the absorption spectrum of 4.37 nM Au NPs in methanol.

Citation: Abo-Alhasan AA, El-Daly SA, El-Hendawy MM, El-Khalfy SH, Ebeid EM (2014) Rapid Induced Aggregation of Gold Nanoparticles by Diolefinic Dyes. J Nanomater Mol Nanotechnol 3:2.

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the band maxima of MSB and gold nanoparticles. The new band is broad and increased slowly with time. This broadening may be attributed the slow rate of interaction. The new band diminished after 12 hours. Visually, the color of the mixture changed from red to violet in a time of about 2 minutes as presented in Figure 8. The stopped-flow instrument was adjusted to follow the appearance of the newly produced band at 690 nm which is characteristics to aggregated Au NPs in all studied cases [57], cf. Figure 9. The effective interactions started at 63.15 seconds and ended at 509.47 seconds. The reaction was assumed to be pseudo first order (where, [MSB] >> [Au NPs]) and the reaction rate constant was 3.25 m s-1 with good correlation factor, R2 = 0.93. This reflects the higher affinity of P2VB toward Au NPs irrespective to MSB.

The absorption spectra of 1×10-5 M DSP after addition of 4.37 nM Au NPs were measured at different time intervals, Figure 10. A new band was observed around 690 nm which is characteristic for Au NPs aggregates [57-59], with an observable consumption of the individual

band maxima of DSP and Au NPs. The new band was broad and increased very slowly with time until diminish after 24 hours. Even after increasing the concentration of the Au NPs from 4.37 nM to 10.93 nM, the interaction with DSP was still too slow to be detected by stopped-flow technique. Figure 11 demonstrates the monitoring of appearance of the newly produced band at 690 nm for ten minutes. Instead, we used the steady-state spectrophotometry to follow the slow change in the absorbance at 690 nm versus time as shown in Figure 12. The interaction between DSP and Au NPs occurred in the minutes rather than the seconds time scale observed in the case of MSB and P2VB indicating that the interaction between DSP and Au NPs was too slow.

Finally, we conclude that the speed of interaction between Au NPs and these dyes goes in the order P2VB >MSB »DSP as a result of the difference in the affinity of their terminal moieties toward the negatively charged citrate- capped Au NPs. This interaction could be described better by the proposed sketch (Figure 13) for the aggregation of citrate- capped gold nanoparticles due to electrostatic interaction with the dye molecules. To confirm this, we performed a quick

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Figure 9: A stopped-flow trace showing absorbance change versus time (in seconds) as a result of the interaction between 1×10-5 M MSB and 10.93 nM gold nanoparticles in methanol (The instrument was set up to follow the newly produced band at 690 nm).

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Figure 10: Absorption spectra of 1×10-5 M DSP in methanol at different time intervals of 2, 120 minutes and 24 hours after addition of 4.37 nM Au NPs.

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Figure 11: A stopped-flow trace showing absorbance change versus time (in seconds) as a result of the interaction between 1×10-5 M DSP in methanol and 10.93 nM Au NPs (The instrument was set up to follow the newly produced band at 690 nm) for ten minutes.

Y = 0.1837 X 0.0152

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Figure 12: Plot of absorbance change at 690 nm versus time (in minutes) for the interaction between 1×10-5 M DSP and 10.93 nM Au NPs in methanol. Data were extracted from absorption spectra in (Figure 10).

Citation: Abo-Alhasan AA, El-Daly SA, El-Hendawy MM, El-Khalfy SH, Ebeid EM (2014) Rapid Induced Aggregation of Gold Nanoparticles by Diolefinic Dyes. J Nanomater Mol Nanotechnol 3:2.

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computational study to check up the affinity of the studied molecules toward Au NPs. The calculations were performed using CAM-B3LYP functional [60] that was implemented in Gaussian 09 [61]. The CAM-B3LYP is the coulomb attenuated version of the B3LYP functional. The computations were done using SMD [63] (Truhlar’s new solvent model, which is dependent on the full electron density of the solute without partitioning into partial charges) solvent models to represent the bulk effect of methanol. The group charges on the two terminals of each molecule are depicted on their optimized skeletons, Figure 14. It is evident that the group charges on both terminals are the same as a result to the centosymmetry of the molecules. This is also confirmed by the zero dipole moments of all molecules. The group charges on the terminals of P2VB, MSB and DSP are 0.22, 0.17 and -0.14 e, respectively. This could explain the order in the affinity of the molecules toward the negatively charged nanoparticles to aggregate and subsequently interpret the estimated rate of interactions.

We conclude that aggregation of nanoparticles can be induced by molecules on their surface and this, in turn, can be used as a means of detecting molecules of interest. This color change is attributed to change of SPR [58,59].

ConclusionsThis work aimed to investigation of the effect of addition of some

diolefinic dyes on the aggregation of gold nanoparticles. It was clear that the all investigated dyes induce aggregations with different rates. This is visually observed by a change in the color of the mixture. The color change is attributed to change of SPR and open the door for practical applications. The aggregation process is pseudo-first order kinetics. The rate of aggregation depends on the group charge of their terminal moieties where the formed aggregate is a result to

the electrostatic interaction between the negatively charged citrate-capped nanoparticles with the relatively positively charged terminals of dyes. The positive group charge on the terminals go in the order P2VB > MSB > DSP. This could explain quite the differentiation in the rate of induced aggregation.

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Citation: Abo-Alhasan AA, El-Daly SA, El-Hendawy MM, El-Khalfy SH, Ebeid EM (2014) Rapid Induced Aggregation of Gold Nanoparticles by Diolefinic Dyes. J Nanomater Mol Nanotechnol 3:2.

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Citation: Abo-Alhasan AA, El-Daly SA, El-Hendawy MM, El-Khalfy SH, Ebeid EM (2014) Rapid Induced Aggregation of Gold Nanoparticles by Diolefinic Dyes. J Nanomater Mol Nanotechnol 3:2.

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Author Affiliation Top 1Chemistry Department, Faculty of Science, Tanta University, Tanta, Egypt2Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia3Chemistry Department, Faculty of Science, Kafrelsheikh University, Kafrelsheikh, Egypt4Misr University for Science and Technology (MUST), 6th of October City, Egypt5Higher Institute for Engineering and Technology, Kafrelsheikh, Egypt

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