Cluster formation between an oxadiazole derivative with metal nanoclusters (Ag/Au/Cu), graphene quantum dot sheets, SERS studies and solvent effects

doi:10.21203/rs.3.rs-1517144/v1

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Cluster formation between an oxadiazole derivative with metal nanoclusters (Ag/Au/Cu), graphene quantum dot sheets, SERS studies and solvent effects

https://doi.org/10.21203/rs.3.rs-1517144/v1

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Interaction of an oxadiazole derivative with Ag/Au/Cu and graphene quantum dots with different solvents is reported theoretically. The adsorption energy is maximum for Cu6 cluster and minimum for Ag6 cluster. The asymmetric charge redistribution between DPMO and M₆s produces an improvement in dipole moment values. The decrease in energy gaps of complexes increased conductivity and metal clusters can be used as a drug sensor. The solvation energies are higher negative in solvent media than in the gaseous media, indicating an enhancement in solvent medium’s stability. Wavefunction studies show that there exist significant noncovalent interactions between metal clusters and oxadiazole that facilitates cluster formation. DPMO is found to form stable clusters with graphene which is evident from the enhancement of Raman activity of the system through SERS also enabling it for sensing DPMO in a mixture.

SERS

DFT

metal clusters

oxadiazole

solvent effects

ALIE

One of the most fascinating fields of research is heterocyclic chemistry. Due to their intriguing biological actions, thiazoles, thiadiazoles, indoles and oxadiazoles are among the most important heterocyclic compounds [1]. New infectious diseases have evolved in recent decades, while formerly treated diseases have resurfaced [2]. Despite the urgent need for novel antimicrobial medicines, progress on these agents in slowing [3]. Oxadiazoles have many properties, likeantiviral, antibacterial, anti-neoplastic, antioxidant, antifungal, inhibitors of tyrosinase and cathepsin K [4–10]. Oxadiazole can also significantly contribute to boosting pharmacological activity [11]. Zibotntan, an important anticancer drug and nesapidil as an antihypertensive agent, are one of the commercially available medicines having the oxadiazole molecule [12, 13]. Oxadiazole derivatives are used in a variety of industries, including fluorescent materials, electro-optical devices and high performance materials in the polymer industry [14–17]. Xu et al. reported biological evaluation oxadiazole acetamide moiety as a novel linker [18]. Chortani et al. reported theoretical studies of oxadiazole linked with benzoypyrimidinones [19]. Synthesis and computational studies of three oxadiazoles are reported by Hamdani et al. [20]. Researchers have studied different oxadiazole derivatives as corrosion inhibitors [21]. Some methoxyphenyl compounds are photo sensitizers that are frequently employed in biochemistry, medical therapies, cell and sensor research [22–24]. Oxadiazole was widely employed as a preferred scaffold in drug development [25–27]. It was frequently utilized as bioisoesters for carbonyl containing compound drugs interacting with receptors via hydrogen bonding interactions [28, 29].

Because M₆ is the smallest experimentally created cluster, clusters of six atom of particular have relevance among numerous homo and bimetallic clusters [30, 31]. Several metals shows SERS enhancement [32–40]. SERS of pyridine was reported by Zuo and Jagodzinski utilizing various metals [41]. SERS with gold is used as a sensor for drug monitoring in blood [42]. Mary et al. reported a number of studies of oxadiazole and methoxyphenyl derivatives [43–52].

Cu, Ag and Au, the coinage metals of group XI has rich coordination chemistry as potent reagents [53, 54]. Unlike their silver analogues, derivatives of copper and gold are known as most active complexes in catalysis, allowing for the use of organo-metallic entities in catalysis and materials research [55]. Silver derivatives on the other hand, are the most widely used metal based drugs in a variety of biological applications [56]. Kleinhans et al. reported photo physical effects of T-shaped coinage metal complexes [57]. Coinage metals with a lower oxidation state have been the subject of research into their usage in OLEDs [58]. In the field of coordination chemistry, complexes containing nitrogen donor atoms and coinage metals are commonly encountered protagonists. These compounds are intriguing not only because of their many structural motifs, but also because many investigations on the potential application of these materials have already been completed, demonstrating their versatility [59–61] .A large variety of luminous coinage metal complexes have been reported in the literature [62]. Interaction of 5-(3,4-dimethoxyphenyl)-3-(3-methoxyphenyl)-1,2,4-oxadiazole (DPMO) with M₆ (M = Ag/ Au/ Cu) clusters are predicted in the present work.

The DFT analysis was used to investigate the essence of proposed structures’ structural, chemical, electronic, thermodynamic properties in order to find a viable DPMO drug detector. All M₆ clusters and DPMO were optimized before adsorption process using Gaussian 16 program’s B3LYP functional and SDD basis set [63, 64]. Energy and frequency calculations were used to establish the structural integrity and natural existence of adsorbents. To create energetically appropriate and persistent conjugated nano structures, we examined the adsorption process of DPMO on nano metal clusters. We investigated thermodynamic terms, changes in enthalpy, entropy and Gibbs free energy to find thermal stability of DPMO and DPMO-M₆ systems. We conducted a thorough examination of the energy of the HOMO, LUMO, DOS and NBO to get electronic confirmation of the interaction between M6 and DPMO. All DPMO-M₆ systems were optimized in various solvents and key features such as solubility, adsorption properties, and electronic properties were estimated to better understand the biological influence [65, 66]. Reaction sites of DPMO-M₆s were examined using Multi-wavefunction by analyzing ALIE, electron localized function, and noncovalent interactions [67].

Optimized geometries of M₆s and DPMO

Fig.1 shows the DPMO and M₆s’ structures, FMOS and MEP plot. The electronic properties of DPMO including as HOMO, LUMO and dipole moment were investigated (Table 1). The dipole moment (DM) of DPMO is 4.8758 Debye, indicating that asymmetric charge distribution which is supported by MEP (Fig.1) with reactive sites around primarily on O, N and C atoms. The Fermi level is given as -4.0764 eV, while E_H and E_Lvalues are -6.1875 and -1.9652 eV (table 1). In order to discover a good adsorbent for DPMO, we conducted a comparison analysis and selected three nanoclusters: M₆ (M=Ag/Au/Cu). The bond lengths for Ag/Au/Cu clusters 2.7299, 2.6989 and 2.3781Å respectively which are perfectly consistent with various theoretical conclusions [68]. The M₆s have zero dipole moments, which mean the charges are evenly distributed across the structure. The FMOs energy values were -5.6128/-6.7837/-5.7301 eV and -2.5823/-3.3766/-2.4718 eV respectively for Ag/Au/Cu clusters and the band gaps are, 3.0305/3.4071/3.2683 (table 1) [69].

Table 1 Chemical descriptors (in eV), solvation free energy and dipole moments of DPMO, M₆ clusters and DPMO-M₆ clusters in different solvents

Systems	E_H	E_L	E_g	Hardness	Fermi level	Electro philicity index	Adsorption energy/SFE (kJ/mol)	Dipole moment (Debye)
DPMO	-6.1875	-1.9652	4.2223	2.1112	-4.0764	3.9354	-	4.8758
Ag₆	-5.6128	-2.5823	3.0305	1.5153	-4.0976	5.5403	-	0
Au₆	-6.7837	-3.3766	3.4071	1.7036	-5.0802	7.5745	-	0
Cu₆	-5.7301	-2.4618	3.2683	1.6342	-4.0960	5.1330	-	0
DPMO-Ag₆	-4.8596	-2.6574	2.2022	1.1011	-3.7585	6.4146	-42.75	11.5349
DPMO-Ag₆ (Toluene)	-4.6864	-2.5576	2.1288	1.0644	-3.6220	6.1626	-65.21	11.8295
DPMO-Ag₆(Dichloromethane)	-4.6534	-2.6591	1.9943	0.9972	-3.6563	6.7028	-84.79	12.0078
DPMO-Ag₆ (Methanol)	-4.6623	-2.5532	2.1091	1.0546	-3.6078	6.1710	-91.77	12.0472
DPMO-Ag₆ (water)	-4.6661	-2.5551	2.1110	1.0555	-3.6106	6.1755	-93.47	12.0549
DPMO-Au₆	-5.7271	-2.8923	2.8348	1.4174	-4.3097	6.5520	-60.26	12.7971
DPMO-Au₆ (Toluene)	-5.6953	-2.8016	2.8937	1.4469	-4.2485	6.2372	-81.87	13.4181
DPMO-Au₆(Dichloromethane)	-5.7418	-2.7889	2.9529	1.4765	-4.2654	6.1609	-101.25	13.8383
DPMO-Au₆ (Methanol)	-5.7712	-2.7927	2.9785	1.4893	-4.2820	6.1556	-108.26	13.9609
DPMO-Au₆ (water)	-5.7793	-2.7940	2.9853	1.4927	-4.2867	6.1551	-109.97	13.9888
DPMO-Cu₆	-4.7064	-2.7328	1.9736	0.9868	-3.7196	7.0102	-67.95	11.4988
DPMO-Cu₆ (Toluene)	-4.8180	-2.6950	2.1230	1.0615	-3.7565	6.6469	-88.38	12.3600
DPMO-Cu₆(Dichloromethane)	-4.9380	-2.6969	2.2411	1.1206	-3.8175	6.5023	-106.64	12.9964
DPMO-Cu₆ (Methanol)	-4.9848	-2.7007	2.2841	1.1421	-3.8428	6.4647	-113.24	13.2090
DPMO-Cu₆ (water)	-4.9965	-2.7018	2.2947	1.1474	-3.8492	6.4563	-114.85	13.2605

Adsorption and desorption processes

To begin, we used the DFT level of theory to examine the structural properties, adsorption energy, thermodynamic properties and other features of DPMO with M₆s in order to find the most energetically favorable conjugated configuration. The DPMO interacts with our studied adsorbents via the oxadiazole ring’s O and N atoms. To further understand the adsorption process, we used the following equation to compute the adsorption energies (Eads) of all conjugated configurations, which are reported in table 1 [70]: E_ads= E_M6-DPMO–E_M6-E_DPMO; E_M6-DPMOrefers to energy of the conjugated structure; E_M6 and E_DPMO are the energies of M₆ and DPMO, respectively. The thermodynamic properties of conjugated structures were also examined to ensure their thermal stability. Reaction is endothermic if ΔH>0 or exothermic when ΔH<0 and ΔG tells us whether the DPMO and MCs have a spontaneous interaction (ΔG<0) or not (ΔG>0). The ΔG and ΔH are given as [71, 72]: ΔU = U_M6-DPMO - U_M6 – U_DPMO, where U us the Gibbs free energy (G) and enthalpy (H).

In the adsorption of DPMO-M6 structures, DPMO interacts with M₆s, at distances of 2.2824, 3.1579 (Ag-N/O), 2.1841, 3.0940 (Au-N/O) and 1.9634, 2.9054 (Cu-N/O). The adsorption energies are, highest for Cu6 cluster (-67.95 kJ/mol), lowest for Ag6 cluster (-42.75 kJ/mol) and -60.26 kJ/mol for Au6 cluster. Furthermore, considerable changes in thermodynamic characteristics were observed for different M₆s (table S1). The exothermic, spontaneous and thermodynamically ordered interactions are indicated by the negative values of above. The frequencies of all systems are positive revealing the natural occurrence of the three examined DPMO-M₆ clusters.

Dipole moment and MEP maps

The non-uniform charge distribution over DPMO causes a dipole moment in the molecule. All adsorbents, M₆s, have zero dipole moment due to symmetric charge distribution across entire structure. All conjugated configurations achieved a dipole moment after contact of the DPMO molecule with all M₆s (table 1). The redistribution of charges between DPMO and M₆s causes this improvement in DM. In the case the DM values are 11.5349/12.7971/11.4988 for DPMO-Ag/Au/Cu systems. We found a trend in the amplification of DM due to interaction of M₆s with DPMO as Au > Ag > Cu from the data analysis. This suggests that the DPMO- M₆s charge flow in the case of Au is substantially larger than in the case of other adsorbents, which explains why DPMO and Au₆ have a stronger affinity. By displaying the greater (positively charged) and lower (negatively charged) electrostatic potential areas of a molecule, the MEP map exposes the asymmetric charge distribution. The MEP surface’s red to blue color scheme denotes the electron-rich electrophilic attack zone and the electron-deficient nucleophilic attack region, respectively. The MEP maps of DPMO-M₆ structures (Fig.2) indicate reduced change in charge density of the M₆s and DPMO surfaces, indicating that the DPMO and the investigated adsorbents (Ag/Au/Cu) have had unfavorable interactions. Furthermore, the red and blue colors are dispersed across DPMO-M₆. For DPMO- M₆s, on the other hand, red color (reduced electrostatic potential) occupies nearly DPMO. The DPMO section is red, whereas the metal cluster portion is blue, indicating that charge transformation has occurred from the M₆s to the DPMO.

FMOs

The FMOs, HOMO and LUMO, are utilized to explain the idea of adsorbent-adsorbate interaction. Furthermore, because of the availability of electrons than can be donated, HOMO is linked to ionization potential, whereas LUMO energy is linked to the electron affinity due to the lack of electrons. The energy gap (E_g), which is used to characterize the electrical and optical properties of conjugated systems are another important parameter. For DPMO- M₆s (table 1), HOMO energies changed from -5.6128 (Ag₆) to -4.8596 (DPMO-Ag₆), -6.7837 (Au₆) to -5.7271 (DPMO-Au₆), -5.7301 (Cu₆) to -4.7064 (DPMO-Cu₆) and LUMO changed from -2.5823, -3.3766, -2.4718 (Ag/Au/Cu-6) to -2.6574, -2.8923, -2.7328 (DPMO-Ag6/Au6/Cu6). The HOMO is centered on the adsorbent MC in all of the investigated DPMO-M₆s conjugated complexes, while the LUMO is spread largely over DPMO and M₆s (Fig.2). As a result, between M₆s and DPMO, there is a shift in the HOMO and LUMO levels. For DPMO- M₆s changes in E_g have been found, which is validated by PDOS studies. The decreases in E_g have been perceived as 27.33, 16.80 and 39.61% for DPMO-Ag6, DPMO-Au6 and DPMO-Cu6 structures. The decrease in E_g is linked to the nanostructures increased conductivity [73]. As a result, the decrease in E_g for the interaction of DPMO with can cause electrical noise, indicating that M₆s could be used as a DPMO drug sensor.

We also calculated the PDOS to demonstrate the availability of newly created states in energy band and therefore realize the orbital hybridization. In the energy gap of M₆s following interaction with DPMO, as shown in Fig.S1 many energy state may be seen. This suggests that all of the suggested DPMO-M₆s conjugated nanostructures have experiences orbital hybridization. As a result, the energy gap of all the DPMO- M₆s has reduced, supporting the change in E_g. The E_g and conductivity (σ) is given by σ = AT^3/2 exp (-Eg/2kT) [74]. Accordingly when energy gap shrinks, the conductivity increases exponentially. This means that the reduction in energy band, which is a critical property for sensing drugs M₆s, generates an electrical signal. Hence the sensitivity of M₆s toward DPMO follows the trend: σ(Cu6) > σ(Ag6) > σ(Au6). As a result, Cu₆ might be said to more sensitive to DPMO than the other two adsorbents and a suitable nanomaterial for detecting DPMO.

Quantum molecular descriptors (QMD)

To decode the details on chemical stability and reactivity of DPMO and M₆s, QMD analyses are required. The QM descriptors are: hardness, η = (E_L-E_H)/2 and electrophilicity index ω = μ²/2η [75]. From table 1, we can observe that η of M₆s has been reduced after interaction with DPMO from 1.5153/1.7036/1.6342 (Ag/Au/Cu) to 1.1011/1.4174/0.9868 (DPMO-Ag/Au/Cu). This indicates that chemical reactivity of the M₆s has increases as compared to bare M₆s. DPMO-MC’s softness on the other hand, have increased from their original structures. In summary, DPMO-Cu₆ conjugated structures have been found to have greater variances in hardness and softness, as well as in the electrophilicity index, when compared to Ag₆ and Au₆. As a result, we can deduce that Cu₆ interacts with the MPDO molecule more than other adsorbents.

NBO analysis

Through charge transfer interaction between adsorbate and adsorbents, NBO analysis provides information on bonding and hybridization [76]. It has been estimated the interaction energy between filled and empty NBOs (table S2). We can see that more electronic charge has passed between intra molecular NBOs, suggesting stabilization. The interacting orbitals belonging to oxadiazole ring and neighboring units give maximum energies with highest values for Cu6-DPMO. The Mulliken charges of O1, N5 and N6 of DPMO are -0.257964, -0.146621 and -0.045512 and the corresponding charges in Ag/Au/Cu-DPMO are: -0.233902, -0.112060, -0.164591/-0.215203, -0.102209, -0.238470/-0.223696, -0.122827, -0.240453 (table S3). Due to the interaction of metal cluster and DPMO the charges in oxadiazole ring show large variations. Most of the other charges of DPMO in DPMO-M₆s also show variations due to interaction with metal atoms.

Solvent effects

We optimized the DPMO-M₆s using PCM model and computed SFE, DM, FMOs and E_g among other things, to understand the influence of polar media with different dielectric constants: 2.38 (toluene), 8.93 (dichloromethane), 32.70 (methanol) and 80.40 (water) (table 1) [77]. The SFE of the DPMO-M₆s in solvents follow the same trend as the adsorption energies of DPMO-M₆s with gaseous state with high values for Cu₆-DPMO. This indicates that DPMO-M6 conjugated structures produced slightly higher negative SFE in solvent media than in the gaseous media, indicating an enhancement in solvent medium’s stability (table 1). Furthermore, the DM of DPMO-M₆s in solvents has increased as compared to gaseous media, implying that the reactivity and solubility of the examined DPMO-M₆s has increased. The ΔEg of DPMO-M₆s conjugated structures in solvents was also calculated and discussed in order to nominate an electrical sensor for the DPMO. In Au/Cu-DPMO clusters energy gap increases in all solvents while for Ag6-DPMO there is a decrease in the Eg values. It means Au₆ and Cu₆ clusters are good sensors as supported by its solvation or adsorption energies. This is also evident from the Raman spectra (Fig.S2) in which in the finger print regions maximum enhancements are for Au/Cu-DPMO clusters due to SERS effects [78, 79].

Average localized ionization energy (ALIE) assay

The ALIE explains the structure and stability of molecules by the nature of electrons. Oxadiazole formed complex with Ag, Au, and Cu metal sheets. The metal sheets like Ag, Au, and Cu have color from blue to red of scale value from 0.00 to 2.00, and complex size ranges from 9.27 to -7.42, from 7.36 to -7.36 from 8.83 to -6.85 Å³, respectively. Fig.3 shows the ALIE of all three metal complexes. The color blue (range 0.00-0.20Å) represents lone-pairs/unreacted electrons within complexes, and sites are all nitrogen (N), oxygen (O), and metals (Ag, Au, and Cu); like red (range 1.80-2.00Å) represents localized/core electrons of complexes, and sites are all heavy atoms like carbon (C), nitrogen (N), oxygen (O), and metals (Ag, Au, and Cu); in the same way bluish-green (range 0.80-1.10 Å) represents the delocalized/mobile electrons, these produce number of resonance structure of those complexes can explain stability, and also create electron rich and poor sites for potentially chemical reactivity like methoxyphenyl-, 1,2-dimethoxyphenyl-, imidazole- group, and few metals close to molecule [80,81].

Electron localized function (ELF) assay

The ELF explains the structure and stability of molecules by the position of electrons. Oxadiazole-metal cluster showed colors from blue to red mention that probability of electron sites 0.00 to 1.00, and complex size ranges from 9.27 to -7.42, from 7.36 to -7.36, and from 8.83 to -6.85 Å^3, respectively. Fig.4 shows the ELF of all three metal complexes. The colored (range 0.80-1.00) noticed that most probability of electrons staying at hydrogen (H) atoms, bonds of C-C, C-N, C-O, and some metals; blue (range 0.00-0.25) noticed that least probability of electrons sites, and also called delocalized/resonance electrons at methoxyphenyl-, 1,2-dimethoxyphenyl-, imidazole- groups with a few metals close to the molecule [82, 83].

Noncovalent interactions (NCI) assay

The NCI explains the stability of complexes by types of hydrogen bonds; these are noncovalent/nonbonded bonds. It is found that there exists significant interaction between the oxadiazole and the clusters. The metal sheets like Ag, Au, and Cu having the color from blue to red scale from -0.05 to 0.05 a.u., are the strength of hydrogen bonds from strong to weak type. Fig.5 shows the NCI of complexes. The formation of strong hydrogen bond from metals Ag, Au, and Cu to hydrogen’s in methoxyphenyl-, 1,2-dimethoxyphenyl-, imidazole- groups, and descending order of them is Cu > Ag > Au; like, weak hydrogen/van der Waals hydrogen bonds formation from metals Ag, Au, and Cu to hydrogen’s in methoxyphenyl-, from O and N atoms to methoxyphenyl-, 1,2-dimethoxyphenyl- groups and from O in methoxy to hydrogen’s in methoxyphenyl-, 1,2-dimethoxyphenyl- groups, and descending order of them is Cu > Au > Ag; alike, the red color notice that hydrogen-hydrogen repulsions, bulky groups repulsions, and aromatic rings repulsions, these interactions between oxadiazole- and methoxyphenyl-, oxadiazole- and 1,2-dimethoxyphenyl-, oxygen and carbon in 1,2-dimethoxyphenyl-, oxygen in methoxy and phenyl- and all metals, and descending order of them is Au > Cu > Ag [84,85].

Prediction of bio-activity through TD-DFT calculations

TD-DFT is always essential for effective molecular modeling. Electronic transition between molecular orbital is a time dependent phenomena [86]. UV absorption spectra and oscillator strength (f) of drug molecule attached with small Ag, Au, and Cu clusters were calculated with TD-DFT method at B3LYP/SDD level of theory to obtain electronic transition states. Our calculated data’s for Ag cluster attached drug molecule shows there are six electronic transitions in the UV region as shown in electronic supplementary Fig.S3 with blue vertical lines and the one with highest oscillator strength “0.029” at 7000cm^-1 which corresponds to the movement of electron from H to L state (where H present HOMO and L present LUMO). This may be attributed to MLCT (metal to ligand charge transfer) .i.e. the charge is transferring from Ag cluster to drug molecule [87] and it is also support our charge transfer mechanism. The other transition are corresponds to H-1 to L, H-2 to L, H-1 to L, H-1 to L, and H to L. Similarly for Au cluster attached with drug molecule exhibit only one electronic transition state with oscillator strength 0.0032 at 15000 cm^-1 (Fig.S3). In this transition the main contribution comes when electron move from HOMO to LUMO state and it is also ascribed as ligand to metal charge transfer. Similar, Cu clusters with drug molecule exhibit six electronic transitions in the UV region with highest oscillator strength 0.068 at 7500 cm^-1 which again due to the jump of electron from the HOMO to LUMO site. The importance of the result obtains from Ag; Cu cluster with drug decides the use of this system in bacterial culturing. Optical density measurements use a wavelength of 600-620 nm to estimate the cell concentration and to track growth pattern [88].

Interaction of Drug and metal cluster + drug over graphene QD sheet

We know graphene is a single-atom thick, two-dimensional sheet of hexagonally arranged carbon atoms. Graphene has free surface π electrons and are capable of forming π–π interactions for loading drug as well as covalent modifications [89, 90]. On the other hand, it is well known that biological activity describes the beneficial or adverse effects of a drug on living matter [91]. If anyhow the biological activity of drug molecule can be increased it will be beneficial for us. To enhance this biological activity, we studied the vibrational Raman properties of present drug molecule over the graphene quantum dots (G-QD). Here we used graphene as a substrate rather than metal surface. The interaction of π electrons (2p orbital) of carbon on graphene with the 2p orbital of oxygen or nitrogen as well as Ag, Au, and Cu increases the signal strength of Raman frequency.

As we can see the Fig.S4, the intensity of Raman activity for drug molecule over graphene QD is 2390au at the frequency 1652.88 cm^-1 while the individual drug molecule has the intensity1889au at the frequency 1659.05 cm^-1. We have also analyzed the Raman activity with metal clusters and found there is a very little bit difference at the frequency level. It can be seen that the Raman activity intensity for Ag₆, Au₆, and Cu₆ attached with drug molecule over graphene QD are 2420au, 2391au, 2253au at the frequency level 1652.88 cm^-1, 1652.5 cm^-1, and 1653.18 cm^-1 respectively. The Raman vibrational data’s for Ag, Au, and Cu clusters with drug molecule over graphene quantum dots shows enhancement of Raman signals. It is very interesting that this combination can be used as a detection of this drug molecule in a biological sample.

The cluster formation of DPMO with different metals was reported with the help of chemical descriptors, solvation effects and wavefunction analysis. Changes in thermodynamic characteristics observed for different M₆s are exothermic, spontaneous and thermodynamically ordered interactions. DPMO-Cu₆ have been found to have greater variances in chemical descriptors when compared to Ag₆ and Au₆ and hence Cu₆ interacts with the MPDO molecule more than other adsorbents. The increase energy gap in Au/Cu-DPMO clusters in all solvents with respect the gaseous state means Au and Cu clusters are good sensors. The cluster formation is stabilized by various noncovalent interactions and it led to favorable change sin electron delocalization in the system .Drug is found to interact with graphene quantum dots also. The enhancement of Raman activity using both clusters indicate it suitability for the development of sensors based on the clusters.

Acknowledgments

The authors express their gratitude to Princess Nourah bint Abdulrahman University Researchers Supporting Project number (PNURSP2022R13), Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia

Author contribution

Jamelah S.Al-Otaibi: Software, Supervision, manuscript preparation and data analysis

Y.Sheena Mary: Supervision, manuscript preparation, conceiving the problem and data analysis

Y.Shyma Mary: Manuscript preparation, conceiving the problem and data analysis and correction

Ravi Trivedi: Software, Supervision, manuscript preparation and data analysis

Brahmananda Chakrabory: Software, Supervision, manuscript preparation and data analysis

Renjith Thomas: Software, Supervision, manuscript preparation and data analysis

Data availability: The supplementary information files include additional materials

Code availability: No new codes have been created. Existing codes were utilized and quoted correctly

Conflict of interest The authors declare no competing interests

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Cluster formation between an oxadiazole derivative with metal nanoclusters (Ag/Au/Cu), graphene quantum dot sheets, SERS studies and solvent effects

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