Corannulene polysulfides: Molecular bowls with multiple arms and flaps

Nucleophilic aromatic substitution of all the chlorine atoms in 1,3,5,7,9-pentachlorocorannulene and in decachloro-corannulene by sodium alkanethiolates gives 1,3,5,7,9- pentakis(1-alkylthio)corannulenes, C20H5(SR)(5), and decakis(1-alkylthio)corannulenes, C-20(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 Angstrom 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.