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Synlett 2004(1): 173-176  
DOI: 10.1055/s-2003-44965
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© Georg Thieme Verlag Stuttgart · New York

Corannulene Polysulfides: Molecular Bowls with Multiple Arms and Flaps

Mihail Bancua, Amarjit K. Raia, Peichao Chenga, Richard D. Gilardib, Lawrence T. Scott*a
a Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467-3860, USA
Fax: +1(617)5526454; e-Mail: lawrence.scott@bc.edu;
b Laboratory for the Structure of Matter, Naval Research Laboratory, Washington, DC 20375, USA
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Publication History

Received 30 August 2003
Publication Date:
04 December 2003 (online)

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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

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Mizyed, S.; Georghiou, P.; Bancu, M.; Scott, L. T. unpublished observations.