Synthesis, characterization, aggregation-induced enhanced emission and solvatochromic behavior of dimethyl 4 '-(diphenylamino)biphenyl-3,5-dicarboxylate: experimental and theoretical studies

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dc.contributor.authorKaraman, Merve
dc.contributor.authorDemir, Nuriye
dc.contributor.authorBilgili, Hakan
dc.contributor.authorYakali, Gul
dc.contributor.authorGokpek, Yenal
dc.contributor.authorDemic, Serafettin
dc.contributor.authorCan, Mustafa
dc.date.accessioned2020-12-01T11:58:55Z
dc.date.available2020-12-01T11:58:55Z
dc.date.issued2020
dc.departmentEge Üniversitesien_US
dc.description.abstractA novel triarylamine derivative dimethyl-4 '-(diphenylamino)biphenyl-3,5-dicarboxylate was synthesized and characterized using spectroscopic and single crystal X-ray diffraction analysis. in addition, theoretical studies, thermogravimetric analysis, cyclic voltammetry and solvent effect studies were also investigated. As a result of solvatochromism, the molecule shows an emission depending on the solvent polarity. Increased polarity caused a red shift of the emission wavelength by 149 nm. in addition, we investigated the intramolecular charge transfer (ICT) and aggregation emission properties with respect to the packing structure of crystalline aggregates. the molecule demonstrates aggregation-induced enhanced emission (AIEE) when the water proportion is greater than 40% in an acetone/water mixture. the maximum emission intensity of the molecule was 2 times higher in an 80% water/acetone mixture. As evidenced by the crystallographic results, the phenyl ring of the compound causes steric hindrance and this hindrance prevents undesirable face to face pi MIDLINE HORIZONTAL ELLIPSIS pi stacking interactions that would inevitably have an adverse effect on the fluorescence efficiency. the crystal packing of the molecule illustrates J-type stacking, which ensures that the crystal is highly fluorescent with a rigid planar structure. the results of DFT calculations are in good agreement with structural and spectroscopic data and verified the compositions of frontier molecular orbitals in similar compounds.en_US
dc.description.sponsorshipIzmir Katip Celebi University Central Research Laboratory; Ege UniversityEge University; DFT calculations; Dokuz Eylul UniversityDokuz Eylul University [2010.KB.FEN.13]en_US
dc.description.sponsorshipThis work was supported by Izmir Katip Celebi University Central Research Laboratory for the Cyclic Voltammeter measurement and TGA analysis, Ege University for NMR measurement, photophysical studies and DFT calculations and Dokuz Eylul University for the use of the Agilent Xcalibur Eos diffractometer (purchased under University Research Grant No: 2010.KB.FEN.13). the presented numerical results were obtained at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA Resources).en_US
dc.identifier.doi10.1039/d0nj01720e
dc.identifier.endpage11506en_US
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issn1144-0546en_US
dc.identifier.issn1369-9261en_US
dc.identifier.issue27en_US
dc.identifier.scopus2-s2.0-85088298149en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage11498en_US
dc.identifier.urihttps://doi.org/10.1039/d0nj01720e
dc.identifier.urihttps://hdl.handle.net/11454/62144
dc.identifier.volume44en_US
dc.identifier.wosWOS:000548246700009en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherRoyal Soc Chemistryen_US
dc.relation.ispartofNew Journal of Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.titleSynthesis, characterization, aggregation-induced enhanced emission and solvatochromic behavior of dimethyl 4 '-(diphenylamino)biphenyl-3,5-dicarboxylate: experimental and theoretical studiesen_US
dc.typeArticleen_US

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