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.
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