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<p>Quercetin, a naturally occurring flavonoid, has garnered heightened attention for optoelectronic and light-harvesting applications. Nonetheless, its comparatively substantial HOMO–LUMO energy gap and limited visible-light absorption impede its practical efficacy. This study examined seven O,O-linked heterocycle-functionalized quercetin derivatives featuring pyridine, pyrrole, tetrahydrofuran, pyrazine, pyridazine, furan, and pyrimidine by DFT and TD-DFT calculations. Geometry optimization and electronic structure simulations were conducted at the B3LYP/6-31G(d) level, while the optical response was assessed using B3LYP and CAM-B3LYP in both the gas phase and ethanol. The findings indicate that heterocyclic functionalization lowers the energy gap of pristine quercetin from 3.892&#xa0;eV to 2.682&#xa0;eV for Q-Fur and 2.747&#xa0;eV for Q-Pyrz. The B3LYP optical calculations indicate significant bathochromic changes, with Q-Pyrz reaching 772.19 nm. CAM-B3LYP yields more conservative wavelengths; yet, the redshift trend persists, with Q-Pyrz exhibiting absorption at 551.11&#xa0;nm in the gas phase and 541.55&#xa0;nm in ethanol. These results validate that the enhanced optical response is not only an artifact of the B3LYP functional or gas-phase calculations. Q-Pyrz demonstrates the most significant wavelength extension, although Q-Tet, Q-Pyrl, Q-Pyr, and Q-Pyri have advantageous oscillator strengths, suggesting their viability as quercetin-derived dyes for optoelectronic and light-harvesting applications.</p>

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Improved optoelectronic properties of quercetin-derived dyes via heterocyclic functionalization: a DFT investigation

  • 期刊论文

  • 发表日期：

    2026年7月17日

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  • Alaa M. Khudhair,
  • Mohammed A. Khammat

摘要

Quercetin, a naturally occurring flavonoid, has garnered heightened attention for optoelectronic and light-harvesting applications. Nonetheless, its comparatively substantial HOMO–LUMO energy gap and limited visible-light absorption impede its practical efficacy. This study examined seven O,O-linked heterocycle-functionalized quercetin derivatives featuring pyridine, pyrrole, tetrahydrofuran, pyrazine, pyridazine, furan, and pyrimidine by DFT and TD-DFT calculations. Geometry optimization and electronic structure simulations were conducted at the B3LYP/6-31G(d) level, while the optical response was assessed using B3LYP and CAM-B3LYP in both the gas phase and ethanol. The findings indicate that heterocyclic functionalization lowers the energy gap of pristine quercetin from 3.892 eV to 2.682 eV for Q-Fur and 2.747 eV for Q-Pyrz. The B3LYP optical calculations indicate significant bathochromic changes, with Q-Pyrz reaching 772.19 nm. CAM-B3LYP yields more conservative wavelengths; yet, the redshift trend persists, with Q-Pyrz exhibiting absorption at 551.11 nm in the gas phase and 541.55 nm in ethanol. These results validate that the enhanced optical response is not only an artifact of the B3LYP functional or gas-phase calculations. Q-Pyrz demonstrates the most significant wavelength extension, although Q-Tet, Q-Pyrl, Q-Pyr, and Q-Pyri have advantageous oscillator strengths, suggesting their viability as quercetin-derived dyes for optoelectronic and light-harvesting applications.