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<p>Density functional theory (M06-2X/6-31G(d)) reveals how mono-functionalizing hexaazatriphenylene (HAT) dimers with pinacolborane (Bpin) or cyano (–C≡N) tailors electronic properties for targeted applications. Molecular electrostatic potential mapping identifies Bpin-installed nucleophilic O-sites/mildly electrophilic B-centers and –C≡N polarized terminus. Functionalization dramatically enhances dipole moments (15–25 × increase to 2.96–4.80 Debye). Binding energy confirms HAT-Bpin superior stability (14.82&#xa0;eV vs. 12.64&#xa0;eV for HAT–C≡N), ideal for robust optoelectronics, while –C≡N moderate binding enables reversible chemosensing. Frontier orbital gaps remain &gt; 5.8&#xa0;eV but subtly widen (Bpin: 5.94&#xa0;eV) or narrow (–C≡N: 5.84&#xa0;eV). Reactivity descriptors show Bpin-induced rigidity (higher hardness) versus –C≡N-driven softness and electrophilicity. Density of states projections validate substituent-specific band edge perturbations. This work establishes mono-functionalization as a strategic tool to engineer HAT platforms prioritizing stability (Bpin) or sensing dynamics (–C≡N) for sustainable technologies.</p> Graphical abstract <p></p>

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Electronic landscape remodeling in 2D HAT dimers: How Bpin and cyano mono-functionalization dictate reactivity and stability from first principles

  • 期刊论文

  • 发表日期：

    2025年12月29日

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  • Huda Alqahtani,
  • Islam Gomaa,
  • Ahmed Refaat

摘要

Density functional theory (M06-2X/6-31G(d)) reveals how mono-functionalizing hexaazatriphenylene (HAT) dimers with pinacolborane (Bpin) or cyano (–C≡N) tailors electronic properties for targeted applications. Molecular electrostatic potential mapping identifies Bpin-installed nucleophilic O-sites/mildly electrophilic B-centers and –C≡N polarized terminus. Functionalization dramatically enhances dipole moments (15–25 × increase to 2.96–4.80 Debye). Binding energy confirms HAT-Bpin superior stability (14.82 eV vs. 12.64 eV for HAT–C≡N), ideal for robust optoelectronics, while –C≡N moderate binding enables reversible chemosensing. Frontier orbital gaps remain > 5.8 eV but subtly widen (Bpin: 5.94 eV) or narrow (–C≡N: 5.84 eV). Reactivity descriptors show Bpin-induced rigidity (higher hardness) versus –C≡N-driven softness and electrophilicity. Density of states projections validate substituent-specific band edge perturbations. This work establishes mono-functionalization as a strategic tool to engineer HAT platforms prioritizing stability (Bpin) or sensing dynamics (–C≡N) for sustainable technologies.

Graphical abstract