Corannulene Polysulfides: Molecular Bowls with Multiple Arms and Flaps

Abstract

Nucleophilic aromatic substitution of all the chlorine ­atoms in 1,3,5,7,9-pentachlorocorannulene and in decachloro­corannulene by sodium alkanethiolates gives 1,3,5,7,9-pentakis(1-alkylthio)corannulenes, C₂₀H₅(SR)₅, and decakis(1-alkylthio)cor­annulenes, C₂₀(SR)₁₀, respectively, with arms of varying lengths attached around the perimeter (R = n-propyl, n-hexyl, and n-dodecyl). The corresponding reaction of decachlorocorannulene with ortho-C₆H₄(SNa)₂ gives pentakis(1,4-benzodithiino)corannulene, a molecular bowl with 6 Å flaps on all five sides. Such compounds represent attractive candidates for the formation of discotic liquid crystals and/or supramolecular complexes with fullerenes and other convex guests.

Key words

nucleophilic aromatic substitutions - sulfur - arenes - polycycles - supramolecular chemistry

References

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  See also ref. [1a]

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5

Mizyed, S.; Georghiou, P.; Bancu, M.; Scott, L. T. unpublished observations.