RSS-Feed abonnieren
DOI: 10.1055/s-2003-44965
Corannulene Polysulfides: Molecular Bowls with Multiple Arms and Flaps
Publikationsverlauf
Publikationsdatum:
04. Dezember 2003 (online)
![](https://www.thieme-connect.de/media/synlett/200401/lookinside/thumbnails/10.1055-s-2003-44965-1.jpg)
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
-
1a
Cheng P.-C. PhD Dissertation Boston College; Chestnut Hill, MA: 1996. -
1b First reported by:
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 - 6
Rai AK. M.S. Thesis Boston College; Chestnut Hill, MA: 1997. -
7a First reported by:
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 For examples of discotic liquid crystals derived from planar 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 Coordinates for C60 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
References
Mizyed, S.; Georghiou, P.; Bancu, M.; Scott, L. T. unpublished observations.