Ma Zikang, Wan Lin, Ji Yude, Wang Weifan, Zhang Gang
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, P. R. China.
Chemistry. 2025 Jun 3;31(31):e202500924. doi: 10.1002/chem.202500924. Epub 2025 Apr 24.
While the classical buckybowls, such as corannulene, and sumanene, have been extensively investigated, research on other molecular bowls containing double neighboring pentagonal rings remains underdeveloped. Here we present the synthesis of nitrogen-doped molecular bowls incorporating adjacent pentagonal motifs with an extended π-conjugated surface. Their molecular curvatures are preserved according to the analyses of bowl-depth, π-orbital axis vector angles, and inversion energy barrier when compared to those of their parent structures. The extended π-conjugation induces the bathochromic shifts of both absorption and emission spectra, the narrowed energy gaps of the frontier molecular orbitals, as well as the enhanced aromatic character in the fused pentagonal rings. Furthermore, the extended aromatic surface enables the binding with fullerene C in solution.
虽然经典的巴基碗，如碗烯和棱晶烷，已经得到了广泛研究，但对其他含有相邻双五元环的分子碗的研究仍不充分。在此，我们报道了一种氮掺杂分子碗的合成方法，该分子碗包含相邻的五元环结构以及扩展的π共轭表面。通过对碗深、π轨道轴矢量角和反转能垒的分析可知，与母体结构相比，它们的分子曲率得以保留。扩展的π共轭导致吸收光谱和发射光谱均发生红移，前沿分子轨道的能隙变窄，以及稠合五元环中的芳香性增强。此外，扩展的芳香表面使得该分子碗能够在溶液中与富勒烯C结合。
