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<p>A novel 5-cyanomethylpyrano[3,2-c]chromene derivative (<b>CPCC</b>,<b> 3</b>) was successfully synthesized through ring opening and recyclization of 3-(6,8-dimethylchromonyl)acrylonitrile (<b>1</b>) with ethyl cyanoacetate under basic conditions. The structure of the obtained product <b>CPCC</b> was confirmed by elemental and spectroscopic analyses. Density functional theory (DFT) calculations at the B3LYP/6–311 +  + G(d,p) level provided an optimized molecular geometry in good agreement with the experimental data and revealed moderate HOMO–LUMO separation with favorable global reactivity descriptors, indicating enhanced electronic delocalization and chemical stability. Molecular electrostatic potential (MEP) and natural bond orbital (NBO) analyses identified the main reactive sites and confirmed effective intramolecular charge transfer within the molecule. Calculated <sup>1</sup>H/<sup>13</sup>C NMR and vibrational frequencies showed close agreement with the experimental spectra, supporting the proposed structure. Time-Dependent Density Functional Theory (TD-DFT) calculations demonstrated pronounced solvent-dependent optical behavior, with clear solvatochromism and reduced optical band gap in polar media, particularly DMSO, indicating improved exciton dissociation efficiency. Thermodynamic analysis over the 200–500&#xa0;K range confirmed the thermal stability of <b>CPCC</b> in the gas phase, while non-linear optical calculations revealed enhanced polarizability and promising optoelectronic potential. Drug-likeness evaluation further suggested that <b>CPCC</b> may serve as a promising scaffold for future pharmaceutical and optoelectronic applications.</p>

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5-Cyanomethylpyrano[3,2-c]chromene-3-carbonitrile: structural and solvent-dependent -thermodynamic behavior, spectral and electrical studies for optoelectronic applications

  • 期刊论文

  • 发表日期：

    2026年6月1日

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  • Shimaa Abdel Halim,
  • Magdy A. Ibrahim,
  • Al-Shimaa Badran

摘要

A novel 5-cyanomethylpyrano[3,2-c]chromene derivative (CPCC, 3) was successfully synthesized through ring opening and recyclization of 3-(6,8-dimethylchromonyl)acrylonitrile (1) with ethyl cyanoacetate under basic conditions. The structure of the obtained product CPCC was confirmed by elemental and spectroscopic analyses. Density functional theory (DFT) calculations at the B3LYP/6–311 +  + G(d,p) level provided an optimized molecular geometry in good agreement with the experimental data and revealed moderate HOMO–LUMO separation with favorable global reactivity descriptors, indicating enhanced electronic delocalization and chemical stability. Molecular electrostatic potential (MEP) and natural bond orbital (NBO) analyses identified the main reactive sites and confirmed effective intramolecular charge transfer within the molecule. Calculated 1H/13C NMR and vibrational frequencies showed close agreement with the experimental spectra, supporting the proposed structure. Time-Dependent Density Functional Theory (TD-DFT) calculations demonstrated pronounced solvent-dependent optical behavior, with clear solvatochromism and reduced optical band gap in polar media, particularly DMSO, indicating improved exciton dissociation efficiency. Thermodynamic analysis over the 200–500 K range confirmed the thermal stability of CPCC in the gas phase, while non-linear optical calculations revealed enhanced polarizability and promising optoelectronic potential. Drug-likeness evaluation further suggested that CPCC may serve as a promising scaffold for future pharmaceutical and optoelectronic applications.