{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,7]],"date-time":"2026-01-07T07:36:57Z","timestamp":1767771417764,"version":"build-2065373602"},"reference-count":56,"publisher":"MDPI AG","issue":"15","license":[{"start":{"date-parts":[[2023,7,31]],"date-time":"2023-07-31T00:00:00Z","timestamp":1690761600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001321","name":"National Research Foundation\u2019s NRF Thuthuka","doi-asserted-by":"publisher","award":["138397","129744"],"award-info":[{"award-number":["138397","129744"]}],"id":[{"id":"10.13039\/501100001321","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Mintek Science Vote Work Package AM27","award":["138397","129744"],"award-info":[{"award-number":["138397","129744"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>We present here the design, synthesis, and photophysical properties of two novel fluorescent zinc (II) complexes, ZnCl2(ImL1)2 and ZnCl2(ImL2)2, containing 4-(1-octyl-1H-imidazol-4-yl)-N,N-diphenyl-[1,1-biphenyl]-4-yl)-4-amine ImL1 and 9-(4-(1-octyl-1H-imidazol-4-yl)-[1,1-biphenyl]-4-yl)-9H-carbazole ImL2 ligands. The newly synthesized free ligands and their zinc (II) complexes were characterized using several spectroscopic techniques; their structures were identified by single-crystal X-ray diffraction; and their photophysical properties have been studied in the context of their chemical structure. The ZnCl2(ImL1)2 and ZnCl2(ImL2)2 complexes showed good thermal stability at 341 \u00b0C and 365 \u00b0C, respectively. Photophysical properties, including UV-Vis absorption spectra in ethanol solution and photoluminescence (PL) in both solid state and ethanol solution, were determined. UV-Vis adsorption data indicated that both free ligands had similar UV-Vis absorption properties, while their Zn (II) complexes had distinctive absorption characteristics. The fluorescence spectra show that both ligands and their corresponding Zn (II) complexes emit violet to cyan luminescence in the solid state at room temperature, while in ethanol solution at the same temperature, they exhibit efficient photoluminescence properties in the UV-A emission spectral region. Because of these photophysical properties, the synthesized ligands and their cognate Zn (II) complexes can be used as scaffolds for the potential development of optoelectronic materials.<\/jats:p>","DOI":"10.3390\/ijms241512260","type":"journal-article","created":{"date-parts":[[2023,7,31]],"date-time":"2023-07-31T10:08:14Z","timestamp":1690798094000},"page":"12260","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Novel Fluorescent Tetrahedral Zinc (II) Complexes Derived from 4-Phenyl-1-octyl-1H-imidazole Fused with Aryl-9H-Carbazole and Triarylamine Donor Units: Synthesis, Crystal Structures, and Photophysical Properties"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6353-4374","authenticated-orcid":false,"given":"Thompho Jason","family":"Rashamuse","sequence":"first","affiliation":[{"name":"Nanotechnology Innovation Centre, Health Platform, Advanced Materials Division, Mintek, Private Bag X3015, Randburg 2125, South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elena Mabel","family":"Coyanis","sequence":"additional","affiliation":[{"name":"Nanotechnology Innovation Centre, Health Platform, Advanced Materials Division, Mintek, Private Bag X3015, Randburg 2125, South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rudolph","family":"Erasmus","sequence":"additional","affiliation":[{"name":"Materials for Energy Research Group, Material Physics Research Institute, School of Physics, University of the Witwatersrand, Private Bag 3, Wits, Johannesburg 2050, South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nomampondo Penelope","family":"Magwa","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of South Africa, Private Bag X6, Florida, Roodepoort 1710, South Africa"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,7,31]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"90","DOI":"10.1016\/j.synthmet.2018.11.017","article-title":"A review on low-molar-mass carbazole-based derivatives for organic light-emitting diodes","volume":"247","author":"Krucaite","year":"2019","journal-title":"Synth. Met."},{"key":"ref_2","first-page":"3033","article-title":"Synthesis and photophysical properties of multi-functional bisimidazolyl phenol zinc (II) complex: Application in OLED, anti-Counterfeiting, and latent fingerprint detection","volume":"6","author":"Kempegowda","year":"2021","journal-title":"Chem. Sel."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Kim, J., Koh, C.W., Uddin, M.A., Ryu, K.Y., Jang, S.R., Woo, H.Y., Lim, B., and Kim, K. (2020). Improving the photostability of small-molecule-based organic photovoltaics by providing a charge percolation pathway of crystalline conjugated polymer. Polymers, 12.","DOI":"10.3390\/polym12112598"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3821","DOI":"10.1002\/adma.201305999","article-title":"Molecular materials for organic photovoltaics: Small is beautiful","volume":"26","author":"Roncali","year":"2014","journal-title":"Adv. Mater."},{"key":"ref_5","first-page":"788","article-title":"Recent advances in organic light-emitting diodes: Toward smart lighting and displays","volume":"4","author":"Zou","year":"2020","journal-title":"Chem. Front."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"20032","DOI":"10.1039\/C5DT02768C","article-title":"Influence of para substituents in controlling photophysical behavior and different non-covalent weak interactions in zinc complexes of a phenol-based \u201cend-off\u201d compartmental ligand","volume":"44","author":"Chakraborty","year":"2015","journal-title":"Dalton Trans."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3366","DOI":"10.1021\/acs.cgd.6b00347","article-title":"(E)-N-(pyridine-2-ylmethylene)arylamine as an assembling ligand for Zn (II)\/Cd (II) Complexes: Aryl substitution and anion effects on the dimensionality and luminescence properties of the supramolecular metal-organic frameworks","volume":"16","author":"Dong","year":"2016","journal-title":"Growth Des."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"17474","DOI":"10.1039\/C5RA23049G","article-title":"Cost-effective solar concentrators based on the red fluorescent Zn (II)-salicylaldiminato complex","volume":"6","author":"Minei","year":"2016","journal-title":"RSC Adv."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"119662","DOI":"10.1016\/j.ica.2020.119662","article-title":"Blue fluorescent zinc (II) complexes based on tunable imidazo[1,5-a]pyridines","volume":"509","author":"Volpi","year":"2020","journal-title":"Inorg. Chim. Acta"},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Fudulu, A., Olar, R., Maxim, C., Sc\u0103e\u0163eanu, G.V., Bleotu, C., Matei, L., Chifiriuc, M.C., and Badea, M. (2020). New cobalt (II) complexes with imidazole derivatives: Antimicrobial efficiency against planktonic and adherent microbes and in vitro cytotoxicity features. Molecules, 26.","DOI":"10.3390\/molecules26010055"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"9777","DOI":"10.1038\/s41598-019-46224-6","article-title":"Selective cytotoxicity and antifungal properties of copper (II) and cobalt (II) complexes with imidazole-4-acetate anion or 1-allylimidazole","volume":"9","author":"Ciepluch","year":"2019","journal-title":"Sci. Rep."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4427","DOI":"10.1039\/C9CC00437H","article-title":"A bio-inspired imidazole-functionalised copper cage complex","volume":"55","author":"Bete","year":"2019","journal-title":"Chem. Commun."},{"key":"ref_13","first-page":"39","article-title":"Structure regulation of nickel (II) complexes with imidazole-tripodal ligand by altering the counteranions and the reaction conditions","volume":"38","author":"An","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1080\/15980316.2020.1802357","article-title":"Imidazole derivatives for efficient organic light-emitting diodes","volume":"21","author":"Ye","year":"2020","journal-title":"Inf. Disp."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Bezvikonnyi, O., Bernard, R.S., Andruleviciene, V., Volyniuk, D., Keruckiee, R., Vaiciulaityte, K., Labanauskas, L., and Grazulevicius, J.V. (2022). Derivatives of imidazole and carbazole as bifunctional materials for organic light-emitting diodes. Materials, 15.","DOI":"10.2139\/ssrn.4110014"},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Yu, P., and Xiao, X. (2021). Non-doped deep-blue OLEDs based on carbazole-\u03c0-imidazole derivative. Materials, 14.","DOI":"10.3390\/ma14092349"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"16173","DOI":"10.1039\/D2TC03601K","article-title":"Recent progress in imidazole based efficient near ultraviolet\/blue hybridized local charge transfer (HLCT) characteristic fluorophores for organic light-emitting diodes","volume":"10","author":"Tagare","year":"2022","journal-title":"Mater. Chem. C"},{"key":"ref_18","first-page":"545","article-title":"Highly Efficient Blue Organic Light-Emitting Diode Based on a Pyrene[4,5-d]Imidazole-Pyrene Molecule","volume":"3","author":"Liu","year":"2021","journal-title":"CCS Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1800258","DOI":"10.1002\/adom.201800258","article-title":"Organic light-emitting diodes based on imidazole semiconductors","volume":"6","author":"Chen","year":"2018","journal-title":"Opt. Mater."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"e02580","DOI":"10.1016\/j.heliyon.2019.e02580","article-title":"Synthesis, crystal structures, and electrochemical properties of ferrocenyl imidazole derivatives","volume":"5","author":"Labulo","year":"2019","journal-title":"Heliyon"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1007\/s00289-017-2015-1","article-title":"Synthesis, photophysical, and electrochemical properties of polyimides of tetraaryl imidazole","volume":"75","author":"Hariharan","year":"2018","journal-title":"Polym. Bull."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"23802","DOI":"10.1039\/D1RA02765D","article-title":"Solubility, thermal, and photoluminescence properties of triphenyl imidazole-containing polyimides","volume":"11","author":"Bai","year":"2021","journal-title":"RSC Adv."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"262","DOI":"10.1016\/j.dyepig.2010.07.005","article-title":"Luminescent properties of some imidazole and oxazole based heterocycles: Synthesis, structure, and substituent effects","volume":"88","author":"Eseola","year":"2011","journal-title":"Dyes Pigments"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Rashamuse, T.J., Mohlala, R.L., Coyanis, E.M., and Magwa, N.P. (2023). A review: Blue fluorescent Zinc (II) complexes for OLEDs\u2014A last five-year recap. Molecules, 28.","DOI":"10.3390\/molecules28135272"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"4921","DOI":"10.1021\/cr900134a","article-title":"Application of metal coordination chemistry to explore and manipulate cell biology","volume":"109","author":"Haas","year":"2009","journal-title":"Chem. Rev."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"7589","DOI":"10.1021\/acs.chemrev.5b00074","article-title":"Light-Emitting self-assembled materials based on d8 and d10 transition metal complexes","volume":"115","author":"Yam","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"11850","DOI":"10.1021\/acs.jpcc.9b02171","article-title":"A novel zinc complex with an ethylenediamine Schiff base for high-luminance blue fluorescent OLED applications","volume":"123","author":"Gusev","year":"2019","journal-title":"Phys. Chem. C"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"113222","DOI":"10.1016\/j.optmat.2022.113222","article-title":"Blue fluorescent zinc (II) complexes bearing Schiff base ligand for solution-processed organic light-emitting diodes with CIEy \u2264 0.09","volume":"134","author":"Solanki","year":"2022","journal-title":"Opt. Mater."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"3436","DOI":"10.1021\/acsaelm.1c00402","article-title":"Schiff base zinc (II) complexes as promising emitters for blue organic light-emitting diodes","volume":"3","author":"Gusev","year":"2021","journal-title":"ACS Appl. Electron. Mater."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"6629","DOI":"10.1002\/adma.201402415","article-title":"Carbazole-based hole-transport materials for efficient solid-state dye-sensitized solar cells and perovskite solar cells","volume":"26","author":"Xu","year":"2014","journal-title":"Adv. Mater."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"12856","DOI":"10.1007\/s10854-020-04021-2","article-title":"Carbazole-based material: Synthesis, characterization, and application as hole transporting material in perovskite solar cells","volume":"32","author":"Magaldi","year":"2021","journal-title":"J. Mater. Sci. Mater. Electron."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"150","DOI":"10.1038\/s41598-017-00271-z","article-title":"Methoxydiphenylamine-substituted fluorene derivatives as hole transporting materials: Role of molecular interaction on device photovoltaic performance","volume":"7","author":"Tiazkis","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1704351","DOI":"10.1002\/adfm.201704351","article-title":"Diphenylamine-substituted carbazole-based hole transporting materials for perovskite solar cells: Influence of isomeric derivatives","volume":"28","author":"Magomedov","year":"2018","journal-title":"Funct. Mater."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"14519","DOI":"10.1021\/jp207585j","article-title":"Hole transport in triphenylamine based OLED devices: From theoretical modeling to properties prediction","volume":"115","author":"Cias","year":"2011","journal-title":"Phys. Chem. A"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"536","DOI":"10.1016\/j.solener.2021.04.055","article-title":"Molecular designing of triphenylamine-based hole-transporting materials for perovskite solar cells","volume":"221","author":"Rezaei","year":"2021","journal-title":"Sol. Energy"},{"key":"ref_36","first-page":"7367","article-title":"Imidazole-based sensitizers containing double anchors for dye-sensitized solar cells","volume":"33","author":"Yen","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"17419","DOI":"10.1039\/D1TC05068K","article-title":"The synthesis and application of novel benzodithiophene based reactive mesogens with negative wavelength dispersion birefringence","volume":"9","author":"Allen","year":"2021","journal-title":"Mater. Chem. C"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"2465","DOI":"10.1139\/v76-350","article-title":"The crystal structure of the complex salt imidazole imidazolium Perchlorate","volume":"54","author":"Quick","year":"1979","journal-title":"Can. J. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1524\/zkri.2013.1605","article-title":"Metal-ligand bond lengths and strengths: Are they correlated? A detailed CSD analysis","volume":"228","author":"Nimmermark","year":"2013","journal-title":"Z. Kristallogr."},{"key":"ref_40","first-page":"324","article-title":"High-Field Solid-State 67Zn NMR Spectroscopy of Several Zinc\u2212Amino Acid Complexes","volume":"A114","author":"Power","year":"2010","journal-title":"Phys. Chem."},{"key":"ref_41","first-page":"m471","article-title":"Dichlorobis(1-methylimidazole)zinc(II)","volume":"E60","author":"Musie","year":"2004","journal-title":"Acta Crystallogr."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1269","DOI":"10.1515\/znb-2016-0168","article-title":"Synthesis, crystal structures, and blue emission of zinc (II) halide complexes of 1-alkyl-imidazole and (\u2212)-nicotine","volume":"71","author":"Hobbollahi","year":"2016","journal-title":"Naturforsch. B Chem. Sci."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1007\/s10973-018-7524-0","article-title":"Spectroscopic (IR, Raman, UV-Vis) study and thermal analysis of 3d-metal complexes with 4-imidazolecarboxylic acid","volume":"134","author":"Wilczewska","year":"2018","journal-title":"J. Therm. Anal. Calorim."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"3860","DOI":"10.1021\/ja00350a021","article-title":"Electronic structure of alkylated imidazoles and electronic spectra of tetrakis(imidazole)copper(II) complexes Molecular structure of tetrakis(1,4,5-trimethylimidazole)copper(II) diperchlorate","volume":"105","author":"Bernarducci","year":"1983","journal-title":"J. Am. Chem. Soc."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1016\/j.orgel.2014.11.024","article-title":"Molecular modification on bisphenanthroimidazole derivative for deep-blue organic electroluminescent material with ambipolar property and high performance","volume":"17","author":"Chen","year":"2015","journal-title":"Org. Electron."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1016\/j.jphotochem.2018.07.039","article-title":"A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species","volume":"365","author":"Mangione","year":"2018","journal-title":"Photochem. Photobiol. A Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1016\/S0022-2313(01)00173-9","article-title":"Electron spectroscopy of carbazole and N- and C-substituted carbazoles in homogeneous media and in solid matrix","volume":"93","author":"Bonesi","year":"2001","journal-title":"J. Lumin."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"5184","DOI":"10.1021\/jp1116855","article-title":"Rational design of organic asymmetric donors D1\u2013A\u2013D2 possessing broad absorption regions and suitable frontier molecular orbitals to match typical acceptors toward solar cells","volume":"115","author":"Tang","year":"2011","journal-title":"Phys. Chem. A"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"109778","DOI":"10.1016\/j.dyepig.2021.109778","article-title":"Triphenylamine-styryl-anthracene derivative without thermal fluorescence quenching property for spectrally stable organic\/inorganic hybrid light-emitting diodes with no UV residue","volume":"196","author":"Huang","year":"2021","journal-title":"Dyes Pigments"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"128619","DOI":"10.1016\/j.molstruc.2020.128619","article-title":"Experimental and computational investigation of polymorphism in methyl 3-hydroxy-4-(piperidin-1-ylmethyl)-2-naphthoate","volume":"1219","author":"Sahoo","year":"2020","journal-title":"J. Mol. Struct."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"202","DOI":"10.1016\/j.poly.2018.08.019","article-title":"Synthesis and photophysical properties of Zn(II) Schiff base complexes possessing strong solvent-dependent solid-state fluorescence","volume":"155","author":"Gusev","year":"2018","journal-title":"Polyhedron"},{"key":"ref_52","unstructured":"(2016). Bruker, APEX-3, SAINT+, Version 6.02 (Includes XPREP and SADABS), Bruker AXS Inc."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0021889812029111","article-title":"WinGX and ORTEP for Windows: An update","volume":"45","author":"Farrugia","year":"2012","journal-title":"Appl. Crystallogr."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"SHELXT-integrated space-group and crystal-structure determination","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1107\/S090744490804362X","article-title":"Structure validation in chemical crystallography","volume":"65","author":"Spek","year":"2009","journal-title":"Acta Cryst. D"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"5353","DOI":"10.1039\/D2RA07897J","article-title":"Luminescence and stability of Tb doped CaF2 nanoparticles","volume":"13","author":"Hasabeldaim","year":"2023","journal-title":"RSC Adv."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/15\/12260\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T20:23:21Z","timestamp":1760127801000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/15\/12260"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,7,31]]},"references-count":56,"journal-issue":{"issue":"15","published-online":{"date-parts":[[2023,8]]}},"alternative-id":["ijms241512260"],"URL":"https:\/\/doi.org\/10.3390\/ijms241512260","relation":{},"ISSN":["1422-0067"],"issn-type":[{"type":"electronic","value":"1422-0067"}],"subject":[],"published":{"date-parts":[[2023,7,31]]}}}