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<p>Nine donor–π–acceptor (D-π-A) 3-benzo-1,3-benzazaphosphole <i>P-</i>oxide (BAPO) derivatives (<b>1–9</b>) are systematically designed and evaluated using density functional theory (DFT) and time-dependent DFT (TD-DFT) for organic photovoltaic and optoelectronic applications. Substituent effects including C = N substitution, halogenation (–F, –Cl, –Br, –CF<sub>3</sub>), and heteroacene fusion are examined on frontier molecular orbitals, energy gaps, absorption and emission spectra, dipole moments, reorganization energies, and charge-transfer characteristics. Multiparameter analysis identifies compounds <b>7–9</b> as the most promising candidates. Specifically, these derivatives exhibit reduced energy gaps, pronounced bathochromic absorption shifts, high oscillator strengths (<i>f</i>), and enhanced intramolecular charge-transfer character. They also display favorable hole reorganization energies (<i>λ</i><sub>h</sub> = 0.225–0.354&#xa0;eV) and frontier orbital alignments compatible with typical fullerene acceptors, indicating efficient charge transport and separation. The results establish clear structure–property relationships within the BAPO platform and provide predictive design principles for phosphorus-based optoelectronic materials, with particular promise for organic light-emitting and bulk heterojunction solar cell applications.</p>

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Computational design of 3-benzo-1,3-benzazaphosphole P-oxide derivatives: structure–property insights for organic optoelectronic applications

  • 期刊论文

  • 发表日期：

    2026年5月20日

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  • Malik Muhammad Shoaib,
  • Fatima Iftikhar,
  • Khurshid Ayub,
  • Tariq Mahmood,
  • Basit Niaz

摘要

Nine donor–π–acceptor (D-π-A) 3-benzo-1,3-benzazaphosphole P-oxide (BAPO) derivatives (1–9) are systematically designed and evaluated using density functional theory (DFT) and time-dependent DFT (TD-DFT) for organic photovoltaic and optoelectronic applications. Substituent effects including C = N substitution, halogenation (–F, –Cl, –Br, –CF3), and heteroacene fusion are examined on frontier molecular orbitals, energy gaps, absorption and emission spectra, dipole moments, reorganization energies, and charge-transfer characteristics. Multiparameter analysis identifies compounds 7–9 as the most promising candidates. Specifically, these derivatives exhibit reduced energy gaps, pronounced bathochromic absorption shifts, high oscillator strengths (f), and enhanced intramolecular charge-transfer character. They also display favorable hole reorganization energies (λh = 0.225–0.354 eV) and frontier orbital alignments compatible with typical fullerene acceptors, indicating efficient charge transport and separation. The results establish clear structure–property relationships within the BAPO platform and provide predictive design principles for phosphorus-based optoelectronic materials, with particular promise for organic light-emitting and bulk heterojunction solar cell applications.