Abstract
Chemical reduction behavior of the indenyl-fused corannulene bowl, monoindenocorannulene (1), was investigated using two alkali metals with different binding abilities, namely Na and Rb. The sodium-induced reaction in THF in the presence of 18-crown-6 ether afforded a solvent-separated ion product, [Na+(18-crown-6)(THF)2]2[12−]·THF (2·THF), which enabled structural evaluation of the “naked” dianion. The controlled addition of the secondary ligand in rubidium-induced reduction reactions allowed modulation of metal coordination and solid-state packing of the doubly-reduced indenocorannulene. Two products with different topologies and metal ion binding, [Rb+(18-crown-6)]2[12−]·THF (3·THF) and [Rb+(18-crown-6)][Rb+(18-crown-6)0.5][12−]·4THF (4·4THF), were isolated and characterized crystallographically. A direct comparison of 1 and 12− using DFT calculation methods provided insights into consequences of two-fold reduction. The significant change in aromaticity was revealed by NICS calculations, while ACID plots showed a good agreement between the negative charge distribution patterns and the observed metal ion binding sites.
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