Wavefunction-based investigation of a fluorinated organic semiconductor
COMPUTATIONAL AND THEORETICAL CHEMISTRY, vol.1266, no.116066, pp.1-35, 2026 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 1266 Issue: 116066
- Publication Date: 2026
- Doi Number: 10.1016/j.comptc.2026.116066
- Journal Name: COMPUTATIONAL AND THEORETICAL CHEMISTRY
- Journal Indexes: Scopus, Science Citation Index Expanded (SCI-EXPANDED), Chemical Abstracts Core, Chimica, INSPEC
- Page Numbers: pp.1-35
- Akdeniz University Affiliated: Yes
Abstract
2-(4-fluorophenyl) - 3 -(4 -hydroxyphenyl)acrylonitrile (F -HPA), a fluorinated π -conjugated organic semiconductor, was synthesized via a green microwave -assisted demethylation strategy and investigated using combined experimental and theoretical approaches. Density functional theory (DFT) calculations showed good agreement with the crystal structure and revealed a resistance to electronic deformation (𝜂 = 1.89 eV) and marked electrophilic character (𝜔 = 4.03 eV) within conceptual DFT framework. TDOS, PDOS, and OPDOS analyses characterized the fragment -resolved orbital compositions, frontier orbital localization, and ground -state bonding/antibonding overlap characteristics of the molecular framework. Harmonic thermodynamic functions ( 𝐶𝑝 , 𝑚 0 , 𝑆𝑚0 , 𝐻𝑚0 ) evaluated across 100 –1000 K under the statistical rigid -rotor/harmonic -oscillator (RRHO ) framework were systematically parameterized using second -order polynomial regressions ( 𝑅 2 ≥ 0.9994). UV –Vis measurements demonstrated concentration -dependent near -ultraviolet absorption at ~320 nm, while Tauc analysis yielded method - dependent optical band -gap estimates of 3.257 –3.180 eV using the conventional procedure and 3.4168 – 3.3981 eV using the automated linear -region selection approach. These findings provide the combined crystallographic, spectroscopic, and molecular electronic analyses provide a structure –electronic –optical description of F -HPA and establish a basis for further investigation of fluorinated acrylonitrile chromophores in near -ultraviolet optoelectronic systems.