Abstract
The 2,4,5-Triphenyl Imidazole (TPI) C21H16N2 samples were deposited as thin film by means of the physical vapor deposition (PVD) on glass and silicon substrates. As well as, three solutions with different concentrations using dimethyl sulfoxide (DMSO) solvent. The physical properties of all samples were investigated using different techniques. The thin film’s morphology was examined using atomic force microscopy (AFM) of the sample on silicon substrates, revealing a highly rough surface. The optical characteristics of both the thin film on glass substrate, the solutions, and the powder were studied through transmittance and absorbance measurements, which helped determine a value of the band gap of 3.45 eV. Photoluminescence and thermal photoluminescence spectroscopy showed the high emission of the material in its different aspects. Theoretical simulations of the HOMO–LUMO gap and electronic absorption spectra were obtained using the density functional theory (DFT) approach.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Ahmed, S.A., James, O.O., Ahmed, R.S., Salau, S.: Theoretical investigations of the optoelectronic properties of some 2, 4, 5-triphenyl imidazole based dyes for probable use as dye-sensitized solar cells. J. Chem. Soc. Niger. (2022). https://doi.org/10.46602/jcsn.v47i4.784
Anoua, R., Touhtouh, S., Rkhis, M., El Jouad, M., Hajjaji, A., Belhora, F., Bakasse, M., Sahraoui, B., Płóciennik, P., Zawadzka, A.: Optical and electronic properties of the natural alizarin dye: theoretical and experimental investigations for DSSCs application. Opt. Mater. 127, 112113 (2022). https://doi.org/10.1016/j.optmat.2022.112113
Asath, R.M., Premkumar, R., Mathavan, T., Benial, A.M.: Structural, spectroscopic and molecular docking studies on 2-Amino-3-Chloro-5-trifluoromethyl pyridine: a potential bioactive agent. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 175, 51–60 (2017). https://doi.org/10.1016/j.saa.2016.11.037
Bai, Wu., Zhizhi, Hu., Yunhua, Lu., Xiao, G., Zhao, H., Zhu, J., Liu, Z.: Solubility, thermal and photoluminescence properties of triphenyl imidazole-containing polyimides. RSC Adv. 11(38), 23802–23814 (2021). https://doi.org/10.1039/d1ra02765d
Casanova, D.: The role of the π linker in donor-π-acceptor organic dyes for high-performance sensitized solar cells. ChemPhysChem 12(16), 2979–2988 (2011). https://doi.org/10.1002/cphc.201100520
Chattaraj, P.K., Sarkar, U., Roy, D.R.: Electrophilicity index. Chem. Rev. 106(6), 2065–2091 (2006). https://doi.org/10.1021/cr040109f
Choi, H., Chung, I.S., Hong, K., Park, C.E., Kim, S.Y.: Soluble polyimides from unsymmetrical diamine containing benzimidazole ring and trifluoromethyl pendent group. Polymer 49(11), 2644–2649 (2008). https://doi.org/10.1016/j.polymer.2008.04.019
Davis, E.A., Mott, N.F.: Conduction in non-crystalline systems V. Conductivity, optical absorption and photoconductivity in amorphous semiconductors. Philos. Mag. J. Theor. Exp. Appl. Phys. 22(179), 903–922 (1970). https://doi.org/10.1080/14786437008221061
de Mello, J.C., Wittmann, H.F., Friend, R.H.: An improved experimental determination of external photoluminescence quantum efficiency. Adv. Mater. 9(3), 230–232 (1997)
Deng, X., Wen, X., Zheng, J., Young, T., Lau, C.F.J., Kim, J., Green, M., Huang, S., Ho-Baillie, A.: Dynamic study of the light soaking effect on perovskite solar cells by in-situ photoluminescence microscopy. Nano Energy 46, 356–364 (2018). https://doi.org/10.1016/j.nanoen.2018.02.024
Fei, Z., Kocher, N., Mohrschladt, C.J., Ihmels, H., Stalke, D.: Single crystals of the disubstituted anthracene 9,10-(Ph2P=S)2C14H8 selectively and reversibly detect toluene by solid-state fluorescence emission. Angew. Chem. Int. Ed. 42(7), 783–787 (2003). https://doi.org/10.1002/anie.200390207
Fitri, A., Benjelloun, A.T., Benzakour, M., McHarfi, M., Hamidi, M., Bouachrine, M.: Theoretical investigation of new thiazolothiazole-based D-π-A organic dyes for efficient dye-sensitized solar cell. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 124, 646–654 (2014). https://doi.org/10.1016/j.saa.2014.01.052
Frau, J., Muñoz, F., Glossma-Mitnik, D.: A molecular electron density theory study of the chemical reactivity of cis- and trans-resveratrol. Molecules 21(12), 1–13 (2016). https://doi.org/10.3390/molecules21121650
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A.: Gaussian 09 Citation. Gaussian Inc., Wallingford (2013)
Gondek, E., Kityk, I.V., Danel, A., Wisla, A., Pokladko, M., Sanetra, J., Sahraoui, B.: Electroluminescence of several pyrazoloquinoline and quinoksaline derivatives. Mater. Lett. 60(27), 3301–3306 (2006). https://doi.org/10.1016/j.matlet.2006.03.051
Hara, K., Kurashige, M., Ito, S., Shinpo, A., Suga, S., Sayama, K., Arakawa, H.: Novel polyene dyes for highly efficient dye-sensitized solar cells. Chem. Commun. 2, 252–253 (2003). https://doi.org/10.1039/b210384b
Hassanien, A.S., Akl, A.A.: Effect of Se addition on optical and electrical properties of chalcogenide CdSSe thin films. Superlattices Microstruct. 89, 153–169 (2016). https://doi.org/10.1016/j.spmi.2015.10.044
He, F., Tian, L., Tian, X., Hai, Xu., Wang, Y., Xie, W., Hanif, M., Xia, J., Shen, F., Yang, B., Li, F., Ma, Y., Yang, Y., Shen, J.: diphenylamine-substituted cruciform oligo(phenylene vinylene)s: enhanced one- and two-photon excited fluorescence in the solid state. Adv. Func. Mater. 17(9), 1551–1557 (2007). https://doi.org/10.1002/adfm.200600518
Kasai, H., Kamatani, H., Okada, S., Oikawa, H.: Size-dependent colors and luminescences of organic microcrystals. Jpn. J. Appl. Phys. 35, L221-223 (1996)
Korpi, A.G., Ţǎlu, S., Bramowicz, M., Arman, A., Kulesza, S., Pszczolkowski, B., Jurečka, S., Mardani, M., Luna, C., Balashabadi, P., Rezaee, S., Gopikishan, S.: Minkowski functional characterization and fractal analysis of surfaces of titanium nitride films. Mater. Res. Express 6(8), 086463 (2019). https://doi.org/10.1088/2053-1591/ab26be
Kumar, R., Asad Ali, S., Mahur, A.K., Virk, H.S., Singh, F., Khan, S.A., Avasthi, D.K., Prasad, R.: Study of optical band gap and carbonaceous clusters in swift heavy ion irradiated polymers with UV-vis spectroscopy. Nucl. Instrum. Methods Phys. Res. Sect. B 266(8), 1788–1792 (2008). https://doi.org/10.1016/j.nimb.2008.01.010
Laouid, A., Belghiti, A.A., Wisniewski, K., Abdelowahed, H., Sahraoui, B., Zawadzka, A.: Generation of red light with intense photoluminescence assisted by forster resonance energy transfer from Znq2 and DCM thin films. Environ. Sci. Pollut. Res. 30, 0123456789 (2022). https://doi.org/10.1007/s11356-022-23217-z
Lougdali, M., El Kouari, Y., Anoua, R., Zazoui, M., El Oudghiri-idrissi, I., Abboud, Y., Zawadzka, A., Sahraoui, B.: Materials today: proceedings study of photophysical properties of Cdq 2 thin film. Mater. Today Proceed. 66, 202–204 (2022a). https://doi.org/10.1016/j.matpr.2022.04.485
Lougdali, M., Elkouari, Y., Zazoui, M., Abboud, Y., Zawadzka, A., Migalska-Zalas, A., Waszkowska, K., Sahraoui, B.: Photoluminescence and nonlinear optical properties of nickel bis-(8-hydroxyquinoline) thin film. Mater. Chem. Phys. 284(March), 126031 (2022b). https://doi.org/10.1016/j.matchemphys.2022.126031
Lougdali, M., El kouari, Y., Zazoui, M., Anoua, R., Abboud, Y., Zawadzka, A., Migalska-Zalas, A., Waszkowska, K., Sahraoui, B.: Experimental and computational analysis of the linear and nonlinear optical properties of magnesium bis-(8-hydroxyquinoline) thin film. J. Alloys Compd. 921, 165947 (2022c). https://doi.org/10.1016/j.jallcom.2022.165947
Obotowo, I.N., Obot, I.B., Ekpe, U.J.: Organic sensitizers for dye-sensitized solar cell (DSSC): properties from computation, progress and future perspectives. J. Mol. Struct. 1122, 80–87 (2016). https://doi.org/10.1016/j.molstruc.2016.05.080
Rakhshi, M., Mohsennia, M., Rasa, H., Sameti, M.R.: First-principle study of ammonia molecules adsorption on boron nitride nanotubes in presence and absence of static electric field and ion field. Vacuum 155, 456–464 (2018). https://doi.org/10.1016/j.vacuum.2018.06.047
Shankar, R., Senthilkumar, K., Kolandaivel, P.: Calculation of ionization potential and chemical hardness: a comparative study of different methods. Int. J. Quant. Chem. 109, 764–771 (2009). https://doi.org/10.1002/qua
Sofiani, Z., Khannyra, S., Boucetta, A., ElJouad, M., Bouchouit, K., Serrar, H., Boukhris, S., Souizi, A., Migalska-Zalas, A.: Nonlinear optical properties of new synthesized conjugated organic molecules based on pyrimidine and oxazepine. Opt. Quant. Electron. 48(5), 1–12 (2016). https://doi.org/10.1007/s11082-016-0549-3
Tamaki, Y., Asahi, T., Masuhara, H.: Nanoparticle formation of vanadyl phthalocyanine by laser ablation of its crystalline powder in a poor solvent. J. Phys. Chem. A 106(10), 2135–2139 (2002). https://doi.org/10.1021/jp012518a
Tian, Z., Chen, Yu., Yang, W., Yao, J., Zhu, L., Shuai, Z.: Low-dimensional aggregates from stilbazolium-like dyes. Angew. Chem. 116(31), 4152–4155 (2004). https://doi.org/10.1002/ange.200454131
Viveka, S., Prabhuswamy, M., Dinesha, D., Lokanath, N.K., Nagaraja, G.K.: Synthesis, crystal structure, and characterization of new 2,4,5-triphenyl imidazole: 4,5-diphenyl-2-(3,4,5-trimethoxyphenyl)-1 h-imidazole. Mol. Cryst. Liq. Cryst. 588(1), 83–94 (2014). https://doi.org/10.1080/15421406.2013.821933
Xiao, D., Xi, Lu., Yang, W., Hongbing, Fu., Shuai, Z., Fang, Y., Yao, J.: Size-tunable emission from. J. Am. Chem. Soc. 125(21), 6740–6745 (2003)
Xie, Z., Yang, B., Cheng, G., Liu, L., He, F., Shen, F., Ma, Y.: Supramolecular interactions induced fluorescence in crystal : anomalous emission of 2, 5-diphenyl-1, 4-distyrylbenzene with all cis double bonds key laboratory for supramolecular structure and materials of Ministry of Education, Jilin University. Chem. Mater. 17(9), 1287–1289 (2005)
Yan, D., Patel, B., Delori, A., Jones, W., Duan, X.: The formation of hydrogen-bond facilitated salts with tunable optical properties: an experimental and theoretical study of 2,4,5-triphenylimidazole. Cryst. Growth Des. 13(1), 333–340 (2013). https://doi.org/10.1021/cg3014927
Zawadzka, A., Płóciennik, P., Strzelecki, J., Łukasiak, Z., Sahraoui, B.: Photophysical properties of Alq3 thin films. Opt. Mater. 36(1), 91–97 (2013). https://doi.org/10.1016/j.optmat.2013.05.001
Zawadzka, A., Waszkowska, K., Karakas, A., Płóciennik, P., Korcala, A., Wisniewski, K., Karakaya, M., Sahraoui, B.: Diagnostic and control of linear and nonlinear optical effects in selected self-assembled metallophthalocyanine chlorides nanostructures. Dyes Pigm. 157, 151–162 (2018). https://doi.org/10.1016/j.dyepig.2018.04.048
Zhao, Y.S., Yang, W., Xiao, D., Sheng, X., Yang, X., Shuai, Z., Luo, Yi., Yao, J.: Single crystalline submicrotubes from small organic molecules. Chem. Mater. 17(25), 6430–6435 (2005). https://doi.org/10.1021/cm051949t
Zhao, Y.S., Xiao, D., Yang, W., Peng, A., Yao, J.: 2,4,5-triphenylimidazole nanowires with fluorescence narrowing spectra prepared through the adsorbent-assisted physical vapor deposition method. Chem. Mater. 18(9), 2302–2306 (2006). https://doi.org/10.1021/cm060102+
Acknowledgements
The thin films and solutions used in this paper were obtained and characterized in the Interdisciplinary Centre for Modern Technologies facilities, NCU, Torun, Poland.
Funding
The authors have not disclosed any funding.
Author information
Authors and Affiliations
Contributions
IE O-I: formal analysis, experimental investigation, theoretical calculations, data curation, writing—original draft, corresponding author. ZS: Writing—review & editing, conception, visualization & supervision. AL: formal analysis, conceptualization. AT: molecular synthesis, resources. AT: theoretical calculations. YE K: visualization, resources. AZ: review & editing, conception, resources, visualization & supervision. All authors reviewed the manuscript.
Corresponding author
Ethics declarations
Conflict of interest
The authors have not disclosed any competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
El Ouedghiri-Idrissi, I., Sofiani, Z., Laouid, A. et al. Experimental and theoretical study on the optical and morphological properties of highly photoluminescent material 2,4,5-triphenyl imidazole. Opt Quant Electron 56, 491 (2024). https://doi.org/10.1007/s11082-023-06186-6
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s11082-023-06186-6