Methoxy-substituted phenylacrylonitrile bearing an m-CF3 group: crystal structure and solvent-dependent excitonic-thermodynamic behavior

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dc.contributor.authorOzen, Leyla Babali
dc.contributor.authorEkici, Oner
dc.contributor.authorGunduz, Bayram
dc.contributor.authorErsanli, Cem Cuneyt
dc.contributor.authorCin, Gunseli Turgut
dc.contributor.authorOzen, Furkan
dc.date.accessioned2026-04-25T14:19:48Z
dc.date.available2026-04-25T14:19:48Z
dc.date.issued2026
dc.departmentSinop Üniversitesi
dc.description.abstractThe structural, electronic, and optical properties of the D-pi-A chromophore 3-(4-methoxyphenyl)-2-(3-(trifluoromethyl)phenyl)acrylonitrile (MTFMAN) were comprehensively investigated using a multiscale approach combining single crystal X-ray diffraction, UV-Vis spectroscopy, and Density Functional Theory (DFT), including Time-Dependent DFT (TD-DFT) and explicit solvent cluster modeling. X-ray analysis confirmed that the compound crystallizes in a monoclinic system (space group P2(1)/n) with a unit cell volume of 1520.4(4) & Aring;(3), stabilized by dominant non-covalent interactions, specifically pipi stacking and C-HF interactions. Optical measurements demonstrated significant solvatochromism; as solvent polarity increased from acetone to DMSO, the absorption maximum shifted from 339 to 344 nm, and the experimental optical band gap decreased from 3.116 to 3.062 eV. TD-DFT calculations confirmed that the dominant Intramolecular Charge Transfer (ICT) is stabilized by the polar DMSO environment. Explicit solvent cluster modeling validated these effects, by identifying a stable C - H & ctdot;O = S interaction with a stabilization energy of -35.58 kJ/mol. Furthermore, thermodynamic properties (heat capacity, entropy, and enthalpy) were evaluated over a wide temperature range of 100-1000 K, with all data accurately fitting second-order polynomial models (R-2 > 0.999). These quantitative results highlight the tunability and thermal stability of MTFMAN for solution-processed optoelectronic applications.
dc.description.sponsorshipScientific and Technological Research Council of Trkiye [TBIdot;TAK, KBAG-119Z608]; Akdeniz University Scientific Research Projects Unit [AU-BAP, FBA-2020-5403 and FDK 2022-6056]; Sinop University
dc.description.sponsorshipOpen access funding provided by the Scientific and Technological Research Council of Turkiye (TUB & Idot;TAK).
dc.identifier.doi10.1007/s10854-026-16754-7
dc.identifier.issn0957-4522
dc.identifier.issn1573-482X
dc.identifier.issue5
dc.identifier.orcid0000-0001-9658-8344
dc.identifier.scopus2-s2.0-105029777147
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1007/s10854-026-16754-7
dc.identifier.urihttps://hdl.handle.net/11486/8199
dc.identifier.volume37
dc.identifier.wosWOS:001688892900003
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer
dc.relation.ispartofJournal of Materials Science-Materials in Electronics
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20260420
dc.subject#BAŞV!
dc.titleMethoxy-substituted phenylacrylonitrile bearing an m-CF3 group: crystal structure and solvent-dependent excitonic-thermodynamic behavior
dc.typeArticle

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