Department of Chemistry, Indian Institute of Technology Ropar, Rupnagar 140001, Punjab, India.
Department of Chemistry, Presidency University, Kolkata 700073, India.
J Org Chem. 2023 May 5;88(9):5473-5482. doi: 10.1021/acs.joc.2c03103. Epub 2023 Apr 11.
-Acenoacenes are attractive synthetic targets, but their non-benzenoid isomeric counterparts were unnoticed. 1-Ethoxyphenanthro[9,10-]acephenanthrylene was synthesized and converted to azulene-embedded , which is a tribenzo-fused non-alternant isomeric motif of -anthracenoanthracene. Aromaticity and single-crystal analyses suggested a formal azulene core for , which showed a smaller highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gap with a charge-transfer absorption band and brighter fluorescence than (quantum yield (Φ): = 41.8%, = 8.9%). The reduction potentials of and were nearly identical, and the observations were further supported by density functional theory (DFT) calculations.
吖啶并[9,10-]吖菲并[9,10-b]荧蒽是一种具有吸引力的合成目标，但它们的非苯并异构体却未被注意到。1-乙氧基菲并[9,10-]吖菲并[9,10-b]荧蒽已被合成，并转化为嵌入氮杂薁的吖啶并[9,10-b]荧蒽，这是一种三苯并稠合的非交替异构体基序。芳香性和单晶分析表明，对于，存在一个形式上的氮杂薁核心，它显示出较小的最高占据分子轨道（HOMO）-最低未占据分子轨道（LUMO）能隙，具有电荷转移吸收带和比[9,10-b]荧蒽更亮的荧光（量子产率（Φ）：= 41.8%，= 8.9%）。和的还原电位几乎相同，这些观察结果进一步得到了密度泛函理论（DFT）计算的支持。
