Constructing 1-Ethoxyphenanthro[9,10-e]acephenanthrylene for the Synthesis of a Polyaromatic Hydrocarbon Containing a
Priyank Kumar Sharma1, Akanksha Babbar1, Dibyendu Mallick2
1Department of Chemistry, Indian Institute of Technology Ropar, Rupnagar 140001, Punjab, India.
Abstract:
peri-Acenoacenes are attractive synthetic targets, but their non-benzenoid isomeric counterparts were unnoticed. 1-Ethoxyphenanthro[9,10-e]acephenanthrylene 8 was synthesized and converted to azulene-embedded 9, which is a tribenzo-fused non-alternant isomeric motif of peri-anthracenoanthracene. Aromaticity and single-crystal analyses suggested a formal azulene core for 9, 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 8 (quantum yield (Φ): 9 = 41.8%, 8 = 8.9%). The reduction potentials of 8 and 9 were nearly identical, and the observations were further supported by density functional theory (DFT) calculations.
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