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<p>Two new optical spiro materials, C<sub>17</sub> H<sub>16</sub> F<sub>3</sub> N O<sub>4</sub> (<b>F1</b>) and C<sub>14</sub> H<sub>12</sub> F<sub>3</sub> N O<sub>4</sub> (<b>F2</b>), have been synthesized. Their structures were determined by X-ray diffraction and characterized using FT-IR, UV–vis, and (<sup>1</sup>H and <sup>13</sup>C) NMR spectroscopies. The crystal structure determinations show compound <b>F1</b>, belongs to the triclinic system, space group P <InlineEquation ID="IEq1"> <EquationSource Format="TEX">\(\overline{1 }\)</EquationSource> </InlineEquation>, with a = 6.1216(14) Å, b = 9.536(3) Å, c = 13.957(4) Å, α = 80.044(7)° Å, β = 86.260(8)°, γ = 81.694(7)°, Mr = 355.31, V = 793.4(3) Å<sup>3</sup>, Z = 2, F(000) = 368. Compound J<b>2</b>, is monoclinic system, space group P2<sub>1</sub>/c with a = 14.932(3) Å, b = 5.355(9) Å, c = 17.732(4) Å, β = 92.21(4)°, Mr = 315.25, V = 1417(2) Å<sup>3</sup>, Z = 4, F(000) = 648. The both compounds form three-dimensional network structures via C–H···O and N–H···O intra- and intermolecular hydrogen bonds. The observed bond lengths, bond angles, vibrational frequencies, and UV–vis absorption peaks were in agreement with the data obtained from DFT calculations. Hirshfeld surface analyses of <b>F1</b> and <b>F2</b> highlighted that F···H/H···F and H···H intermolecular interactions were significant contributors. The TG/DTA demonstrated that both compounds possessed strong thermal stability. The energy gaps (ΔE<sub>HOMO-LUMO</sub>) for <b>F1</b> and <b>F2</b> were calculated to be 4.369&#xa0;eV and 4.316&#xa0;eV, respectively. Potential electrophilic and nucleophilic sites were identified through MEP analysis. Additionally, NBO and Mulliken analyses were also studied.</p> Graphical Abstract <p>Two new nonlinear optical spiro materials containing CF3 group have been obtained, C17 H16 F3 N O4 (F1) and C14 H12 F3 N O4 (F2) and their structures were determined by FT-IR, UV–vis, TG analysis, (1H and 13C) NMR spectroscopies, and single crystal crystallography. The vibrational spectra, UV–vis spectra of F1 and F2 were compared to the predicted values using the level of B3LYP/6-31G(d,p). The HOMO–LUMO energies, NBO, MEP, NLO, Milliken charge distribution, TG/DTA and fluorescence behavior were also studied.</p>

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Crystal Structures, TG/DTA Study, Hirshfeld Surface Analysis, Optical and Computational Study of Two New Spiro Compounds Containing (Trifluoromethyl)phenylamino Group

  • 期刊论文

  • 发表日期：

    2025年11月12日

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  • Wulan Zeng,
  • Xia Wang,
  • Bing Lu,
  • Shuxian Zhang,
  • Daiyao Yue

摘要

Two new optical spiro materials, C17 H16 F3 N O4 (F1) and C14 H12 F3 N O4 (F2), have been synthesized. Their structures were determined by X-ray diffraction and characterized using FT-IR, UV–vis, and (1H and 13C) NMR spectroscopies. The crystal structure determinations show compound F1, belongs to the triclinic system, space group P \(\overline{1 }\) , with a = 6.1216(14) Å, b = 9.536(3) Å, c = 13.957(4) Å, α = 80.044(7)° Å, β = 86.260(8)°, γ = 81.694(7)°, Mr = 355.31, V = 793.4(3) Å3, Z = 2, F(000) = 368. Compound J2, is monoclinic system, space group P21/c with a = 14.932(3) Å, b = 5.355(9) Å, c = 17.732(4) Å, β = 92.21(4)°, Mr = 315.25, V = 1417(2) Å3, Z = 4, F(000) = 648. The both compounds form three-dimensional network structures via C–H···O and N–H···O intra- and intermolecular hydrogen bonds. The observed bond lengths, bond angles, vibrational frequencies, and UV–vis absorption peaks were in agreement with the data obtained from DFT calculations. Hirshfeld surface analyses of F1 and F2 highlighted that F···H/H···F and H···H intermolecular interactions were significant contributors. The TG/DTA demonstrated that both compounds possessed strong thermal stability. The energy gaps (ΔEHOMO-LUMO) for F1 and F2 were calculated to be 4.369 eV and 4.316 eV, respectively. Potential electrophilic and nucleophilic sites were identified through MEP analysis. Additionally, NBO and Mulliken analyses were also studied.

Graphical Abstract

Two new nonlinear optical spiro materials containing CF3 group have been obtained, C17 H16 F3 N O4 (F1) and C14 H12 F3 N O4 (F2) and their structures were determined by FT-IR, UV–vis, TG analysis, (1H and 13C) NMR spectroscopies, and single crystal crystallography. The vibrational spectra, UV–vis spectra of F1 and F2 were compared to the predicted values using the level of B3LYP/6-31G(d,p). The HOMO–LUMO energies, NBO, MEP, NLO, Milliken charge distribution, TG/DTA and fluorescence behavior were also studied.