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Updated: Apr 29, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Substituent-induced modulation of proaromaticity in benzo-fused fluorenophenalene exhibiting a low-lying LUMO
Sakshi Sahewal1, Suman Sharma1, Dibyendu Mallick2
1Department of Chemistry, Indian Institute of Technology Ropar, Rupnagar 140001, Punjab, India. chmsdas@iitrpr.ac.in.
Abstract:
Fluorenophenalene (FP) is an underexplored proaromatic polycyclic hydrocarbon. Herein, we report the synthesis of benzo-fused FPs bearing aryls (mesityl, C6H2F3 and C6F5) of varying electronic character as apical substituents of the cyclopenta-unit with large HOMO/LUMO coefficients. Benzo-fusion expands the p-quinoidal conjugation length by forming a polyene-like subunit, while electron-deficient aryls improve the electronic communication. As a result, the HOMO-LUMO gap decreases as the core aromaticity increases. Replacing a mesityl pendant with C6H2F3 and C6F5 lowers the LUMO energy, steadily stabilizing it from -3.08 eV to -3.64 eV and -4.20 eV, respectively, highlighting our design efficacy.
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