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, C20 H5 (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 -C6 H4 (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
1a Cheng P.-C.
PhD Dissertation
Boston College;
Chestnut Hill, MA:
1996.
1b Cheng P.-C.
Scott LT.
8th International Symposium. on Novel Aromatic Compounds
Abstract number 8:
Braunschweig;
Germany:
1995.
2a Seiders TJ.
Baldridge KK.
Elliott EL.
Grube GH.
Siegel JS.
J. Am. Chem. Soc.
1999,
121:
7439
2b Seiders TJ.
Elliott EL.
Grube GH.
Siegel JS.
J. Am. Chem. Soc.
1999,
121:
7804
2c Grube GH.
Elliott EL.
Steffens RJ.
Jones CS.
Baldridge KK.
Siegel JS.
Org. Lett.
2003,
5:
713
3 Mizyed S.
Georghiou P.
Bancu M.
Cuadra B.
Rai AK.
Cheng P.
Scott LT.
J. Am. Chem. Soc.
2001,
123:
12770
4 Ruoff RS.
Tse DS.
Malhotra R.
Lorents DC.
J. Phys. Chem.
1993,
97:
3379
5 Mizyed, S.; Georghiou, P.; Bancu, M.; Scott, L. T. unpublished observations .
6 Rai AK.
M.S. Thesis
Boston College;
Chestnut Hill, MA:
1997.
7a Cheng P.-C.
Scott LT. In
Abstract of Papers, 208th National Meeting of the American Chemical Society
Abstract number ORGN-087:
Am. Chem. Soc.;
Washington DC:
1994.
7b Xie SY.
Deng SL.
Huang RB.
Yu LJ.
Zheng LS.
Chem. Phys. Lett.
2001,
343:
458 ; and references cited therein
7c Samdal S.
Hedberg L.
Hedberg K.
Richardson AD.
Bancu M.
Scott LT.
J. Phys. Chem.
2003,
107:
411
7d See also ref.
[1a
8 per (1-alkylthio)aromatics, see: Spielberg N.
Luz Z.
Poupko R.
Praefcke K.
Kohne B.
Pickardt J.
Horn K.
Z. Naturf., A: Phys. Sci.
1986,
41:
855
9 60 were taken from a C60 :bis(cyclooctasulfur) clathrate crystal structure: Roth G.
Adelmann P.
Appl. Phys. A
1993,
56:
169
10 Wei CH.
Acta Crystallogr., Sect. B
1971,
27:
1523
11 Lovell JM.
Beddoes RL.
Joule JA.
Tetrahedron
1996,
52:
4745
12 Behrens U.
Calleja RD.
Dotze M.
Franke U.
Gunsser W.
Klar G.
Kudnig J.
Olbrich F.
Martinez ES.
Sanchis MJ.
Zimmer B.
J. Mater. Chem.
1996,
6:
547
13 Friederichs S.
Kudnig J.
Klar G.
Z. Naturforsch., B: Chem. Sci.
1996,
51:
1295
