Amantadine antiparkinsonian drug adsorption on the AlN and BN nanoclusters: A computational study

JID:PLA AID:126128 /SCO Doctopic: Nanoscience

[m5G; v1.261; Prn:14/11/2019; 13:19] P.1 (1-7)

Physics Letters A ••• (••••) ••••••

Contents lists available at ScienceDirect

Physics Letters A www.elsevier.com/locate/pla

Amantadine antiparkinsonian drug adsorption on the AlN and BN nanoclusters: A computational study Xianghong Sun a , Xiaona Wan a , Guichen Li b , Jing Yu c,∗ , Vahid Vahabi d,∗ a

Elderly Ward, Section Two, Qingdao Mental Health Center, Qingdao, Shandong, 266034, China Clinical Psychology Division, Qingdao Mental Health, Qingdao, Shandong, 266034, China c Emergency Department, Qingdao Municipal Hospital, Qingdao, Shandong, 266011, China d Young Researchers and Elite club, Central Tehran Branch, Islamic Azad University, Tehran, Iran b

a r t i c l e

i n f o

Article history: Received 6 August 2019 Received in revised form 30 October 2019 Accepted 4 November 2019 Available online xxxx Communicated by R. Wu Keywords: Sensor Nanocage Density functional Adsorption

a b s t r a c t To find a sensor for Amantadine (AM) antiparkinsonian drug, we studied its interaction with Al12 N12 and B12 N12 nanoclusters by density functional theory calculations. The AM molecule attaches via its –NH2 group to the Al or B atoms of Al12 N12 or B12 N12 with Gibbs free energy change about −31.5 or −26.1 kcal/mol. Increasing the AM concentration, the interaction becomes weaker due to steric effects. The AM adsorbs on the Al12 N12 and B12 N12 with two different mechanisms, including electrostatic and charge transfer, respectively. The AM significantly reduces the Al12 N12 work function from 4.50 to 3.66 eV, increasing the electron field emission. Thus, the AlN cluster may be a work function type sensor. Upon the AM adsorption on the BN cage, the HOMO level is largely destabilized, reducing the Eg from 6.84 to 5.01 eV which largely increases the electrical conductivity. This indicates that the BN cluster may be a potential electronic sensor. © 2019 Elsevier B.V. All rights reserved.

1. Introduction Amantadine (1-amino-adamantine, AM) clinically applied for influenza infection, Parkinson’s disease, or hepatitis treatment [1]. Occasionally hallucinations, nightmares, anxiety, jitteriness are the major amantadine side effects [2]. The AM drug is mostly used in the bird flu treatment and swine transmissible gastroenteritis. It has been indicated that the AM drug has harmful effects on animals [3]. The U. S. Food and Drug Administration has prohibited the AM use for poultry breeding and livestock [3]. Recently, a consumer panic caused by an outbreak of “fast-growing chicken” emerged. Also, the normal or therapeutic AM concentration in blood is 60–310 mg ml−1 and a higher concentration is harmful and toxic [4]. Thus, it is vital to design an effective, rapid, and simple AM sensor for its detection in blood, foods and other biological specimens. Now, the methods for AM detection include fluorescence, high-performance liquid, Micellar electrokinetic and gas chromatographies, and, spectrophotometric and potentiometric methods [5–7]. Besides these complicated and expensive methods, it has been shown that the sensors based on the nanomaterials

*

Corresponding authors. E-mail addresses: [email protected] (J. Yu), [email protected] (V. Vahabi). https://doi.org/10.1016/j.physleta.2019.126128 0375-9601/© 2019 Elsevier B.V. All rights reserved.

may sense different chemicals at low levels due to the high surface/volume ratio [8–17]. Different nanoclusters, nanosheets, and nanotubes are prevalent resources for chemical sensors [14–23]. For example, using density functional theory (DFT) calculations, the adsorption of 9,10-anthraquinone (AQ) and its derivatives, i.e., benzofuro[5,6-b]furan-4,8-dione (BFFD), benzo[1,2-b: 4,5-b ]dithipphene4,8-dione (BDTD) and pyrido[3,4-g]isoquinoline-5,10-dione (PID), on monolayer graphene and hexagonal boron nitride (h-BN) is had been investigated [24]. The binding energies range from 1.06 to 1.31eV, showing a strong physisorption. The calculated binding energies of the four organic molecules are in the order: BFFD < BDTD < AQ < BDTD < PID < BDTD < BFFD < PID on both graphene and BN nanosheets. Also, in another study, the adsorption of phenanthraquinone (PQ), pyromellitic dianhydride (PMDA) and their derivatives, i.e., benzo[1,2-b:4,3-b ]difuran-4,5-dione (BDFD), benzo[1,2-b:4,3-b ]dithiophene-4,5-quinone (BDTQ), 3,8-phenanthroline-5,6-dione (PAD), pyromellitic dithioanhydride (PMDT), pyromellitic diimide (PMDI) and 1,4,5,8-anthracenetetrone (ATO) on graphene has been studied by means of DFT calculations [25]. A sequence of the calculated binding energies from weak to strong is found to be BDFD < BDTQ < PMDA ≤ PMDI < PMDT < PQ < PAD < ATO. Recently, a great attention has been devoted to the inorganic aluminum nitride (AlN) and boron nitride (BN) nanostructures, in-

JID:PLA

AID:126128 /SCO Doctopic: Nanoscience

[m5G; v1.261; Prn:14/11/2019; 13:19] P.2 (1-7)

X. Sun et al. / Physics Letters A ••• (••••) ••••••

2

Fig. 1. The optimized structures of (a) A112 N12 nanocluster, (b) B12 N12 nanocluster, and (c) AM molecule. Table 1 Adsorption energy (Ead , kcal/mol) for AM adsorption on the AlN nanocluster (Fig. 2). Energy of Fermi level (EF ), work function (), HOMO, and LUMO, and HOMO-LUMO energy gap (Eg ) in eV. The Eg indicates the change of Eg after the adsorption process. The  indicates the change of  after the adsorption process. Q is NBO charge on the AM molecule in the complex state. Structure

Ead

EHOMO

EF

ELUMO

Eg

%Eg



%

AIN cage H.1 N.1

–

−6.48 −6.25 −5.60

−4.50 −4.39 −3.66

−2.52 −2.54 −1.72

3.96 3.71 3.88

–

4.50 4.39 3.66

–

−0.8 −38.4

cluding nanosheets, nanochains, nanocones, nanoclusters and nanotubes because of their unusual mechanical and electronic properties, and exceptional thermal and chemical stabilities [26–34]. The AlN and BN nanostructures have attracted the attention of the gas sensor researcher [35–41]. Some (XY)n nanoclusters (X=B, Al, . . . and Y=N, P, . . .) have been previously explored, demonstrating that fullerene-like nanocluster X12 Y12 is the most stable structure [42,43]. Wu et al. [44] have investigated the structure and energy of (AlN)n nanoclusters (n = 2–41), presenting that the Al12 N12 is thermodynamically the most stable nanocluster. It has been revealed that the Al12 N12 nanocage can sense NO gas at the presence of CO molecules [45]. Wang et al. [46] predicted that the Al12 N12 nanocluster might be an ideal compound for H2 storage under ambient conditions. Oku et al. have synthesized the B12 N12 nanocluster, and this cluster has been used for recognition of NO2 , tetrachlorodibenzodioxine, NO, CO, etc. [47–49]. Here, we will investigate the adsorption behavior and the electronic response of the X12 N12 (X=Al or B) nanoclusters toward AM, using density functional theory (DFT) calculations to find a proper chemical sensor. 2. Computational methods GAMESS program was used to perform all of the calculations [50]. Energy calculations, optimization of structures, frontier molecular orbitals (FMO), natural bond orbitals (NBO), electronic, and density of states (DOS) analyses were performed by applying B3LYP functional and 6-31G(d) basis set. We applied the dispersion term of Grimme “D” to predict the weak interaction appropriately. It should be noted that the zero-point energy (ZPE) was neglected here because Gholizadeha et al. [51] have validated that ZPE significantly affects the activation energies, but for adsorption energy calculation, it can be neglected. The review of the literature indicates that B3LYP is an adequate functional for calculating electronic and structural properties of different nanomaterials [52–57]. The adsorption energy of AM (Ead ) is calculated as follows:

Ead = E (complex) − E (cluster) − E (AM) + EBSSE

(1)

where E (cluster) is the energy of an AlN or a BN nanocluster. E (complex) is the energy of an AlN or BN nanocluster with an AM molecule adsorbed on its outward. EBSSE is the basis set superposition error energy calculated by the counterpoise approach [58].

−6.3 −2.0

−2.4 −18.7

μ

Q –

1.14 7.70

−0.01 0.12

The HOMO-LUMO energy gap (Eg ) of nanographenes and its complexes is considered as:

Eg = ELUMO − EHOMO

(2)

where EHOMO and ELUMO are the energies of HOMO and LUMO, respectively. We applied the GaussSum program to draw the DOS schemes [59]. We have calculated vibrational frequencies to show that all of the structures are in a local minimum, and also to obtain the thermodynamic data. 3. Results and discussion The X12 N12 nanoclusters (Fig. 1) consist from 8 hexagonal and 6 tetragonal rings with 36 X-N bonds. These bonds are two kinds including B64 and B66 bonds with equilibrium bond length of 1.85 and 1.79 for AlN cage, and 1.48, and 1.43 Å for BN cage, respectively. The B66 bonds are shared between two six-membered rings and B64 bonds are shared by a four- and a six-membered ring. The B64 bonds are shorter than B66 bonds due to the larger strain in the tetragonal rings in comparison to the hexagons. The results in Table 1, show that the energies of HOMO and LUMO levels of AlN nanocluster are about −6.48 and −2.52 eV, respectively. Therefore, its Eg is about 3.95 eV. For BN cage, the energies of HOMO and LUMO levels are about −7.70 and −0.86 eV, respectively, and its Eg is about 6.84 eV. As shown in Fig. 1, the AM molecule has two different heads which can attack the clusters, including H atoms and –NH2 group. Therefore, we optimized the AM/XN complexes with different initial structures and obtained two local minima for each nanocluster, as displayed in Fig. 2. The results of adsorption energies in Tables 1 and 2 show that the most stable complex is that in which the AM molecule adsorbs on the X atom of XN cage via its N atom of –NH2 group named AlN-N or BN-N (Fig. 2) for AlN or BN cage. To understand this phenomenon, Fig. 3 shows the HOMO and LUMO profiles of AM molecule, revealing that the HOMO level mainly localized on the –NH2 group and the LUMO on the remained structure. Thus, the –NH2 group can firmly attach to the electron deficient X atom with a charge transfer of about 0.12 and 0.16 e from AM molecule to AlN and BN nanocages, respectively. In the AlN-N complex, the interaction distances N. . .Al is about 2.03 Å and the predicted adsorption energy about −38.4 kcal/mol. These values N. . .B distance and adsorption energy in the case of BN cage is about 1.64 Å and −31.3 kcal/mol, respectively. The

JID:PLA AID:126128 /SCO Doctopic: Nanoscience

[m5G; v1.261; Prn:14/11/2019; 13:19] P.3 (1-7)

X. Sun et al. / Physics Letters A ••• (••••) ••••••

3

Table 2 Adsorption energy (Ead , kcal/mol) for AM adsorption on the BN nanocluster (Fig. 2). Energy of Fermi level (EF ), work function (), HOMO, and LUMO, and HOMO-LUMO energy gap (Eg ) in eV. The Eg indicates the change of Eg after the adsorption process. The  indicates the change of  after the adsorption process. Q is NBO charge on the AM molecule in the complex state. Structure

Ead

EHOMO

EF

ELUMO

Eg

%Eg



%

BN H.2 N.2

–

−7.70 −6.12 −6.78

−4.28 −3.36 −3.94

−0.86 −0.05 −1.11

6.84 6.63 5.01

–

4.28 3.36 3.94

–

−0.5 −31.3

−3.1 −26.7

−21.4 −7.9

μ

Q –

1.29 9.01

−0.02 0.16

Fig. 3. The HOMO and LUMO profiles of AM molecule.

Fig. 2. Optimized structures of different AM/AlN or AM/BN nanocluster complexes. The distances are in Å.

change of Gibbs free energy (G) is calculated to be about −31.5 and −26.1 kcal/mol at 1 atm and 298 K for AlN-N and BN-N complexes, respectively. The more positive values of G compared to the adsorption energies indicate that upon the AM adsorption, the entropy reduces. After the AM adsorption on the AlN-N complex, the Al atom is projected out, and the B64 and B66 bonds are elongated to 1.83 and 1.90 Å, respectively. In the BN-N complex, these bonds are predicted to be about 1.51 and 1.57 Å, respectively, indicating a strong interaction. Our results indicate that the adsorption of AM molecule on the AlN cage is stronger than that on the BN

cage and the AlN-N complex is more stable than the BN-N one by about 5.4 kcal/mol. Here, we will discuss in detail the reason for this phenomenon. NBO analysis indicates that upon the AM adsorption, the hybridization of adsorbing X atoms tends to change from sp2 to sp3 accompanied by a structural deformation so that the X atom projects out of the plane. In the pristine AlN and BN cages, the value of N-X-N angles of tetragonal ring is about 94.1◦ and 98.2◦ , respectively, indicating more curvature in the construction of Al12 N12 . This matter and larger Al-N bonds in the Al12 N12 (compared to the B-N ones) make the structure of AlN nanocage more flexible and the Al atoms more favorable site for AM molecule adsorption. Also, it is well known that the energy difference between the electrophile agent LUMO and the nucleophile agent HOMO is a critical factor in the HOMO/LUMO interactions. Our predicted HOMO energy for AM is about −6.11 eV, and the results of Tables 1 and 2 indicate that the LUMO level of AlN cage is lower than that of BN cage by about 1.16 eV. This suggests that the HOMO/LUMO interaction between AM and AlN nanocage will be stronger. The second stable AM/XN complex is that in which the AM molecule attacks the three X-N bonds of the XN clusters via its three H atoms, as shown in Fig. 2. We found that the AM molecule is adsorbed on the B64 bonds instead of B66 bonds because the tetragonal ring has more strain energy compared to the hexagonal ring. The adsorption energies for complexes AlN-H and BN-H (Fig. 2) are calculated to be about −0.8 and −0.5 kcal/mol, and a charge about −0.01 and −0.02 e is transferred from cluster to the AM molecule, respectively. To explore the concentration effect on the adsorption of AM molecule, we additionally considered the adsorption of 2, 3, and 4 AM molecules on the Al12 N12 (Fig. 4). To this purpose, we studied the adsorption of AM molecule from its NH2 -head as it was exposed to produce the most stable complex AlN-N. Our calculated adsorption energies per molecule are about −37.1, −30.3, and −21.3 kcal/mol for 2, 3 and 4 AM molecules adsorbed on the cluster, respectively. This indicates the adsorption energy decreases with the increase in the number of adsorbed AM molecules, which may be due to the steric hindrance.

JID:PLA

AID:126128 /SCO Doctopic: Nanoscience

4

[m5G; v1.261; Prn:14/11/2019; 13:19] P.4 (1-7)

X. Sun et al. / Physics Letters A ••• (••••) ••••••

Fig. 4. Optimized structures of 2, 3 and 4 AM adsorbed on the AlN nanocluster.

3.1. Electronic properties For investigating the sensitivity of the electronic properties of AlN and BN nanocages to the AM molecule, we used two parameters, including Eg and work function (). It has been shown repeatedly that the Eg can be a good indicator for determining the sensitivity of nanomaterials to chemicals. The reason for this matter is the existence of a relationship between the Eg and the conduction electron population as follows [60]:

N = A T3/2 exp(−Eg /2kT)

(3) 3 3/ 2

where k is the Boltzmann’s constant, and A (electrons/m K ) is a constant. Many papers have shown that the results of using this formula are confirmed by the results of laboratory work [60–62]. Eq. (3) states that a reduction in the Eg rises the population of conduction electrons exponentially. This causes an increase in electrical conductivity, connecting to the presence of the chemical in the environment. We also investigated the effect of the AM adsorption on the Fermi level and  of the nanoclusters, which are the key factors in the -type sensors. The -type detectors apply a Kelvin oscillator instrument to calculate the values of work function after and before attaching a chemical [63]. If the adsorption of a molecule changes the  of a sensor, it affects the gate voltage, generating an electrical signal, helping the chemical recognition [64]. The work function is assumed to be the amount of energy which is necessary to dig an electron from the Fermi level.

 = Vel(+∞) − EF

(4)

where EF is Fermi level energy, and Vel (+∞) is the electron electrostatic potential energy far from the material surface, expected to be zero, and. Supposing Vel(+∞) = 0, can write  = −EF . The Fermi level energy can be calculated as follows:

EF = EHOMO + (ELUMO − EHOMO )/2

(5)

Fig. 5. The HOMO and LUMO profiles of the most stable complex of AM molecule adsorbed on the AlN nanocluster.

The Fermi level change; thus, the variation of work function  in a sensor can change the field emission amount the classical Richardson Dushman equation [65]:

j = AT2 exp(−/kT)

(6)

where j the electron current densities from the surface of a material, A is called the Richardson constant (A/m2 ), and T is the temperature (K). Table 1 shows that when an AM molecule is adsorbed on the Al12 N12 via most stable or second most stable complexes, the HOMO and LUMO levels are significantly affected but the Eg is

JID:PLA AID:126128 /SCO Doctopic: Nanoscience

[m5G; v1.261; Prn:14/11/2019; 13:19] P.5 (1-7)

X. Sun et al. / Physics Letters A ••• (••••) ••••••

5

Fig. 6. Partial density of state plot for the most stable complex of AM molecule adsorbed on the BN nanocluster.

slightly changed. Thus, the Al12 N12 cannot be an electronic sensor based on the Eg for AM molecule. Also, our calculated Eg values for 2, 3, and 4 AM-adsorbed AlN clusters are about 3.70, 3.68, and 3.67 eV, respectively, indicating that by increasing the concentration of AM the Eg is not changed sensibly. But in the most stable AlNN complex, the work function of the AlN nanocluster is decreased mainly from 4.50 to 3.66 eV. This is due to the larger destabilization of HOMO level compared to the LUMO level of the AlN cluster. Our FMO analysis shows that the HOMO level in the complex Al-N is entirely shifted on the AM molecule (Fig. 5) in consistence with the large HOMO energy change. We can conclude that the field emission amount will increase based on the Eq. (6) upon the AM adsorption on the AlN nanocluster, and thus, it may be a proper work function based sensor for AM detection. Table 2 displays that when an AM molecule is adsorbed on the B12 N12 via most stable or second most stable complexes, the HOMO and LUMO levels are significantly affected. In the most stable complex BN-N, after AM adsorption, the HOMO level is largely destabilized, and the LUMO is slightly stabilized. These changes in the FMO levels significantly reduces the Eg of the BN nanocage from 6.84 to 5.01 eV. This reduction in the Eg largely increases the electrical conductivity of the BN nanocluster, which indicates that the cluster may be a potential electronic sensor for the AM detection. Partial DOS plot (Fig. 6) demonstrates that after the adsorption of AM molecule, a new state is created within the Eg of BN nanocage at −6.87 eV, which significantly decreases the Eg . The new state is originated from AM molecule, as shown in the partial DOS plot. The FMO analysis shows that the HOMO level in the complex BN-N is shifted entirely on the AM molecule (Fig. 6) in consistence with the large HOMO energy change. Unlike the AlN nanocage, in the most stable complex of AM/BN, the Fermi level, and thus, the work function is slightly changed, indicating that the BN nanocage cannot be a work function based sensor for AM molecule. The strength of interaction and recovery time are crucial matters for sensor development. Based on the following equation, by increasing the G of a reaction, the longer recovery time is expected [23]:

τ = υ0−1 exp(−G/kT)

(7)

where k is the Boltzmann’s constant (∼ 2.0 × 10−3 kcal/mol.K), T is the temperature, and υ0 is the attempt frequency. For the strong interactions in the case of AlN and BN nanoclusters, our calculated G is about −27.5 and −20.3 kcal/mol, and thus, the recovery time of AM molecule from the surface is predicted to be about

137 and 0.11 s at 350 K and the vacuum ultraviolet light (υ ∼ 1018 s−1 ), respectively. The results show that these clusters benefit from a short recovery time. As a summary, we showed that the AlN nanocluster may act as a work function type sensor for AM molecule, but the BN cluster is an electronic sensor. To understand this phenomenon, we performed a Morokuma analysis on the most stable AlN-N and BN-N complexes. The results indicate that about 67% of the interaction in the AlN-N complex is electrostatic type, but this interaction is about 18% in the BN-N complex, and the interaction in this complex is mainly charged transfer type. A large charge transfer of about 0.16 e (Table 2) confirms the results of Morokuma analysis. Therefore, the different mechanisms of the interaction differently affect the Eg and work function. 4. Conclusions We have studied the AM adsorption on the AlN and BN nanocages by using DFT calculations to find a chemical sensor. The AM drug clinically applied for influenza infection, Parkinson’s disease, or hepatitis treatment. Occasionally hallucinations, nightmares, anxiety, jitteriness are the major amantadine side effects. Thus, it is vital to design an effective, rapid, and simple AM sensor for its detection in blood, foods and other biological specimens. We showed that the AM molecule prefers to attach the clusters via its N atom with adsorption energy of −38.1 and −31.5 kcal/mol for AlN and BN nanocages, respectively. By increasing the number of AM molecules, the adsorption energy per molecule becomes less negative because of steric hindrance. Two different mechanisms are predicted for AM interaction with AlN and BN nanocages including electrostatic and covalent, respectively. Our results indicate that the AlN nanocluster may be promising work function type sensor for AM molecule but the BN cluster is a potential electronic sensor. By AM adsorption on the AlN nanocluster, its work function significantly reduces from 4.50 to 3.66 eV, increasing the electron field emission current from the nanocluster surface. Upon the AM adsorption on the BN cage, the HOMO level is largely destabilized causing the Eg of the BN nanocage to reduce from 6.84 to 5.01 eV. This reduction in the Eg largely increases the electrical conductivity of the BN nanocluster which helps to detect AM molecules. Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

JID:PLA

AID:126128 /SCO Doctopic: Nanoscience

6

[m5G; v1.261; Prn:14/11/2019; 13:19] P.6 (1-7)

X. Sun et al. / Physics Letters A ••• (••••) ••••••

References [1] W. Davies, R. Grunert, R. Haff, J. McGahen, E. Neumayer, M. Paulshock, J. Watts, T. Wood, E. Hermann, C. Hoffmann, Antiviral activity of 1-adamantanamine (amantadine), Science 144 (1964) 862–863. [2] R.F. Suckow, Separation methods for tricyclic antiviral drugs, J. Chromatogr., B, Biomed. Sci. Appl. 764 (2001) 313–325. [3] L. Xu, S. Peng, L. Liu, S. Song, H. Kuang, C. Xu, Development of sensitive and fast immunoassays for amantadine detection, Food Agric. Immunol. 27 (2016) 678–688. [4] P.M. Bélanger, O. Grech-Bélanger, Gas—liquid chromatographic determination of plasma and urinary levels of amantadine in man, J. Chromatogr., B, Biomed. Sci. Appl. 228 (1982) 327–332. [5] Y. Yun, M. Pan, G. Fang, Y. Yang, T. Guo, J. Deng, B. Liu, S. Wang, Molecularly imprinted electrodeposition o-aminothiophenol sensor for selective and sensitive determination of amantadine in animal-derived foods, Sens. Actuators B, Chem. 238 (2017) 32–39. [6] Y. Li, Y. Gao, Y. Li, S. Liu, H. Zhang, X. Su, A novel fluorescence probing strategy based on mono-[6-(2-aminoethylamino)-6-deoxy]-β -cyclodextin functionalized graphene oxide for the detection of amantadine, Sens. Actuators B, Chem. 202 (2014) 323–329. [7] C. Shuangjin, F. Fang, L. Han, M. Ming, New method for high-performance liquid chromatographic determination of amantadine and its analogues in rat plasma, J. Pharm. Biomed. Anal. 44 (2007) 1100–1105. [8] Seyyed Amir Siadati, Karolina Kula, Esmaiel Babanezhad, The possibility of a two-step oxidation of the surface of C20 fullerene by a single molecule of nitric (V) acid, Chem. Rev. Lett. 2 (2019) 2–6. [9] A. Kakanakova-Georgieva, G.K. Gueorguiev, S. Stafström, L. Hultman, E. Janzén, AlGaInN metal-organic-chemical-vapor-deposition gas-phase chemistry in hydrogen and nitrogen diluents: first-principles calculations, Chem. Phys. Lett. 431 (2006) 346–351. [10] Ezzatollah Najafi, Farnaz Behmagham, Niloofar Shaabani, Nasrin Shojaei, Crystal structure and luminescence properties of a new nanostructure lead(II) complex: a precursor for preparation of pure phase nanosized PbO, Chem. Rev. Lett. 2 (2019) 13–20. [11] N. Hellgren, T. Berlind, G.K. Gueorguiev, M.P. Johansson, S. Stafström, L. Hultman, Fullerene-like BCN thin films: a computational and experimental study, Mater. Sci. Eng. B 113 (2004) 242–247. [12] R.B. dos Santos, R. Rivelino, F. de B. Mota, G.K. Gueorguiev, Exploring hydrogenation and fluorination in curved 2D carbon systems: a density functional theory study on corannulene, J. Phys. Chem. A 116 (2012) 9080–9087. [13] Musa Heidari, Nezhad Janjanpour, Mahshad Vakili, Shahla Daneshmehr, Khodadad Jalalierad, Fatemeh Alipour, Study of the ionization potential, electron affinity and HOMO-LUMO gaps in the smal fullerene nanostructures, Chem. Rev. Lett. 1 (2018) 45–48. [14] A.A. Peyghan, S.F. Rastegar, N.L. Hadipour, DFT study of NH3 adsorption on pristine, Ni- and Si-doped graphynes, Phys. Lett. A 378 (2014) 2184–2190. [15] M. Pashangpour, A.A. Peyghan, Adsorption of carbon monoxide on the pristine, B- and Al-doped C 3 N nanosheets, J. Mol. Model. 21 (2015) 116. [16] R. Rivelino, R.B. dos Santos, F. de Brito Mota, G.K. Gueorguiev, Conformational effects on structure, electron states, and Raman scattering properties of linear carbon chains terminated by graphene-like pieces, J. Phys. Chem. C 114 (2010) 16367–16372. [17] F. Parandin, J. Jalilian, J. Jalilian, Tuning of electronic and optical properties in ZnX (X=O, S, Se and Te) monolayer: hybrid functional calculations, Chem. Rev. Lett. 2 (2019) 76–83. [18] L. Chernozatonskii, Carbon nanotube elbow connections and tori, Phys. Lett. A 170 (1992) 37–40. [19] D. Yang, S. Wang, Q. Zhang, P. Sellin, G. Chen, Thermal and electrical transport in multi-walled carbon nanotubes, Phys. Lett. A 329 (2004) 207–213. [20] A.A. Peyghan, H. Soleymanabadi, Adsorption of H2S at Stone–Wales defects of graphene-like BC3: a computational study, Mol. Phys. 112 (2014) 2737–2745. [21] Y. Mei, X. Wu, X. Shao, G. Huang, G. Siu, Formation mechanism of alumina nanotube array, Phys. Lett. A 309 (2003) 109–113. [22] N. Zhevago, V. Glebov, Channeling of fast charged and neutral particles in nanotubes, Phys. Lett. A 250 (1998) 360–368. [23] N.L. Hadipour, A. Ahmadi Peyghan, H. Soleymanabadi, Theoretical study on the Al-doped ZnO nanoclusters for CO chemical sensors, J. Phys. Chem. C 119 (2015) 6398–6404. [24] Y.-X. Yu, A dispersion-corrected DFT study on adsorption of battery active materials anthraquinone and its derivatives on monolayer graphene and h-BN, J. Mater. Chem. A 2 (2014) 8910–8917. [25] Y.-X. Yu, Binding energy and work function of organic electrode materials phenanthraquinone, pyromellitic dianhydride and their derivatives adsorbed on graphene, ACS Appl. Mater. Interfaces 6 (2014) 16267–16275. [26] M. Samadizadeh, S.F. Rastegar, A.A. Peyghan, F− , Cl− , Li+ and Na+ adsorption on AlN nanotube surface: a DFT study, Physica E 69 (2015) 75–80. [27] C. Wang, X. Luo, S. Zhang, Q. Shen, L. Zhang, Effects of nitrogen gas ratio on magnetron sputtering deposited boron nitride films, Vacuum 103 (2014) 68–71.

[28] J. Beheshtian, A.A. Peyghan, Z. Bagheri, M. Kamfiroozi, Interaction of small molecules (NO, H2 , N2 , and CH4 ) with BN nanocluster surface, Struct. Chem. 23 (2012) 1567–1572. [29] Z. Bagheri, A.A. Peyghan, DFT study of NO2 adsorption on the AlN nanocones, Comput. Theor. Chem. 1008 (2013) 20–26. [30] A.V. Moradi, A.A. Peyghan, S. Hashemian, M.T. Baei, Theoretical study of thiazole adsorption on the (6, 0) zigzag single-walled boron nitride nanotube, Bull. Korean Chem. Soc. 33 (2012) 3285–3292. [31] J. Beheshtian, H. Soleymanabadi, A.A. Peyghan, Z. Bagheri, A DFT study on the functionalization of a BN nanosheet with PC-X, (PC=phenyl carbamate, X=OCH3 , CH3 , NH2 , NO2 and CN), Appl. Surf. Sci. 268 (2012) 436–441. [32] M. Tosa, K. Yoshihara, Surface precipitation of boron nitride on the surface of stainless steel/boron nitride film, Vacuum 41 (1990) 1873–1875. [33] J. Beheshtian, A.A. Peyghan, M.B. Tabar, Z. Bagheri, DFT study on the functionalization of a BN nanotube with sulfamide, Appl. Surf. Sci. 266 (2013) 182–187. [34] N. Kostoglou, K. Polychronopoulou, C. Rebholz, Thermal and chemical stability of hexagonal boron nitride (h-BN) nanoplatelets, Vacuum 112 (2015) 42–45. [35] M. Rezaei-Sameti, E. Samadi Jamil, The adsorption of CO molecule on pristine, As, B, BAs doped (4, 4) armchair AlNNTs: a computational study, J. Nanostruct. Chem. 6 (2016) 197–205. [36] J. Beheshtian, A.A. Peyghan, Z. Bagheri, Sensing behavior of Al-rich AlN nanotube toward hydrogen cyanide, J. Mol. Model. 19 (2013) 2197–2203. [37] Z. Goodarzi, M. Maghrebi, A.F. Zavareh, Z.-B. Mokhtari-Hosseini, B. Ebrahimihoseinzadeh, A.H. Zarmi, M. Barshan-tashnizi, Evaluation of nicotine sensor based on copper nanoparticles and carbon nanotubes, J. Nanostruct. Chem. 5 (2015) 237–242. [38] K. Yum, M.-F. Yu, Measurement of wetting properties of individual boron nitride nanotubes with the Wilhelmy method using a nanotube-based force sensor, Nano Lett. 6 (2006) 329–333. [39] E. Salih, M. Mekawy, R.Y.A. Hassan, I.M. El-Sherbiny, Synthesis, characterization and electrochemical-sensor applications of zinc oxide/graphene oxide nanocomposite, J. Nanostruct. Chem. 6 (2016) 137–144. [40] A. Soltani, A. Ahmadi Peyghan, Z. Bagheri, H2 O2 adsorption on the BN and SiC nanotubes: a DFT study, Physica E 48 (2013) 176–180. [41] C. Zhi, Y. Bando, C. Tang, D. Golberg, Boron nitride nanotubes, Mater. Sci. Eng., R Rep. 70 (2010) 92–111. [42] D.L. Strout, Structure and stability of boron nitrides: isomers of B12N12, J. Phys. Chem. A 104 (2000) 3364–3366. [43] R. Wang, D. Zhang, C. Liu, Theoretical prediction of a novel inorganic fullerenelike family of silicon–carbon materials, Chem. Phys. Lett. 411 (2005) 333–338. [44] H.-S. Wu, F.-Q. Zhang, X.-H. Xu, C.-J. Zhang, H. Jiao, Geometric and energetic aspects of aluminum nitride cages, J. Phys. Chem. A 107 (2003) 204–209. [45] J. Beheshtian, A.A. Peyghan, Z. Bagheri, Selective function of Al12 N12 nano-cage towards NO and CO molecules, Comput. Mater. Sci. 62 (2012) 71–74. [46] Q. Wang, Q. Sun, P. Jena, Y. Kawazoe, Potential of AlN nanostructures as hydrogen storage materials, ACS Nano 3 (2009) 621–626. [47] F. Jensen, H. Toftlund, Structure and stability of C24 and B12N12 isomers, Chem. Phys. Lett. 201 (1993) 89–96. [48] H.-S. Wu, X.-Y. Cui, X.-F. Qin, D.L. Strout, H. Jiao, Boron nitride cages from B12 N12 to B36N36: square–hexagon alternants vs boron nitride tubes, J. Mol. Model. 12 (2006) 537–542. [49] L. Mahdavian, Using of B12 N12 nano-cage for detection and reduction of 2, 3, 7, 8-Tetrachlorodibenzodioxine (TCDD), Sens. Lett. 14 (2016) 280–284. [50] M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, K.A. Nguyen, S. Su, T.L. Windus, M. Dupuis, J.A. Montgomery, J. Comput. Chem. 14 (1993) 1347–1363. [51] R. Gholizadeh, Y.-X. Yu, N2O+CO reaction over Si- and Se-doped graphenes: an ab initio DFT study, Appl. Surf. Sci. 357 (2015) 1187–1195. [52] S. Mohammadi, M. Musavi, F. Abdollahzadeh, S. Babadoust, A. Hosseinian, Application of nanocatalysts in C-Te cross-coupling reactions: an overview, Chem. Rev. Lett. 1 (2018) 49–55. [53] J. Beheshtian, A.A. Peyghan, Z. Bagheri, Detection of phosgene by Sc-doped BN nanotubes: a DFT study, Sens. Actuators B, Chem. 171 (2012) 846–852. [54] S.A. Siadati, S. Rezazadeh, Switching behavior of an actuator containing germanium, silicon-decorated and normal C20 fullerene, Chem. Rev. Lett. 1 (2018) 77–81. [55] F. Behmagham, Z. Asadi, Y. Jamal Sadeghi, Synthesis, spectroscopic and computational investigation of bis (3-methoxyphenylthio) ethyl) naphthalene, Chem. Rev. Lett. 1 (2018) 68–76. [56] J. Beheshtian, A. Ahmadi Peyghan, Z. Bagheri, Hydrogen dissociation on dienefunctionalized carbon nanotubes, J. Mol. Model. 19 (2012) 255–261. [57] E. Babanezhad, A. Beheshti, The possibility of selective sensing of the straightchain alcohols (including methanol to n-pentanol) by using the C20 fullerene and C18NB nano cage, Chem. Rev. Lett. 1 (2018) 82–88. [58] S.F. Boys, F. Bernardi, Calculation of small molecular interactions by differences of separate total energies - some procedures with reduced errors, Mol. Phys. 19 (1970) 553–561. [59] N. O’Boyle, A. Tenderholt, K. Langner, Cclib: a library for package-independent computational chemistry algorithms, J. Comput. Chem. 29 (2008) 839–845.

JID:PLA AID:126128 /SCO Doctopic: Nanoscience

[m5G; v1.261; Prn:14/11/2019; 13:19] P.7 (1-7)

X. Sun et al. / Physics Letters A ••• (••••) ••••••

[60] A. Ahmadi Peyghan, N. Hadipour, Z. Bagheri, Effects of Al-doping and doubleantisite defect on the adsorption of HCN on a BC2N nanotube: DFT studies, J. Phys. Chem. C 117 (2013) 2427–2432. [61] M. Eslami, V. Vahabi, A.A. Peyghan, Sensing properties of BN nanotube toward carcinogenic 4-chloroaniline: a computational study, Physica E 76 (2016) 6–11. [62] M. Samadizadeh, A.A. Peyghan, S.F. Rastegar, Sensing behavior of BN nanosheet toward nitrous oxide: a DFT study, Chin. Chem. Lett. 26 (2015) 1042–1045.

7

[63] I. Baikie, S. Mackenzie, P. Estrup, J. Meyer, Noise and the Kelvin method, Rev. Sci. Instrum. 62 (1991) 1326–1332. [64] G. Korotcenkov, Sensing layers in work-function-type gas sensors, in: Handbook of Gas Sensor Materials, Springer, 2013, pp. 377–388. [65] O. Richardson, Electron emission from metals as a function of temperature, Phys. Rev. 23 (1924) 153–157.