Synthesis 2003(10): 1521-1525
DOI: 10.1055/s-2003-40526
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Syntheses of Hexabenzocoronene Derivatives

Subir K. Sadhukhan, Christine Viala, André Gourdon*
NanoScience Group, CEMES-CNRS, BP3447, 29 Rue J. Marvig, 31055 Toulouse, France
Fax: +33(562)257999; e-Mail: gourdon@cemes.fr;
Further Information

Publication History

Received 31 March 2003
Publication Date:
08 July 2003 (online)

Abstract

The syntheses of four hexabenzo[bc,ef,hi,kl,no,qr]coronene (HBC) derivatives have been carried out. Double Knoevenagel condensation of the benzil 5 with the ketone 6 gave the 2,3,4,5-tetrakis(4-tert-butylphenyl)cyclopenta-2,4-dien-1-one (7). Diels-Alder addition of 7 with di(4-tert-butylphenyl)acetylene, 4-[(4-tert-butylphenyl)ethynyl]-1,1′-biphenyl (9) or 1-tert-butyl-4-(phenylethynyl)benzene (11) gave the substituted hexaphenylbenzene 8, 10 and 12 which were cyclodehydrogenated to yield 1, 2 and 3, respectively. Similarly, condensation of 5 with dibenzylketone yielded the cyclopentadienone 13 which gave, by cycloaddition with di-(4-tert-butylphenyl)acetylene, the tetrasubstituted hexaphenylbenzene 14 which was cyclodehydrogenated to furnish 4.

    References

  • 2 Moresco F. Meyer G. Rieder KH. Tang H. Gourdon A. Joachim C. Phys. Rev. Lett.  2001,  86:  672 
  • 3 Loppacher C. Guggisberg M. Pfeiffer O. Meyer E. Bammerlin M. Luthi R. Schlittler R. Gimzewski JK. Tang H. Joachim C. Phys. Rev. Lett.  2003,  90: art. no.-066107
  • 4 Qiu XH. Nazin GV. Ho W. Science  2003,  299:  542 
  • 5 Gimzewski JK. Joachim C. Science  1999,  283:  1683 
  • 6 Gourdon A. Eur. J. Org. Chem.  1998,  2797 
  • 7 Langlais VJ. Schlittler RR. Tang H. Gourdon A. Joachim C. Gimzewski JK. Phys. Rev. Lett.  1999,  83:  2809 
  • 8 Rosei F. Schunack M. Jiang P. Gourdon A. Laegsgaard E. Stensgaard I. Joachim C. Besenbacher F. Science  2002,  296:  328 
  • 9 Viala C. Secchi A. Gourdon A. Eur. J. Org. Chem.  2002,  4185 
  • See for instance:
  • 10a Biasutti MA. Rommens J. Vaes A. De Feyter S. De Schryver FD. Herwig P. Müllen K. Bull. Soc. Chim. Belg.  1997,  106:  659 
  • 10b Brand JD. Kubel C. Ito S. Müllen K. Chem. Mat.  2000,  12:  1638 
  • 10c Brown SP. Schnell I. Brand JD. Müllen K. Spiess HW. J. Am. Chem. Soc.  1999,  121:  6712 
  • 10d Brown SP. Schnell I. Brand JD. Müllen K. Spiess HW. PCCP Phys. Chem. Chem. Phys.  2000,  2:  1735 
  • 10e Fechtenkotter A. Saalwachter K. Harbison MA. Müllen K. Spiess HW. Angew. Chem. Int. Ed.  1999,  38:  3039 
  • 10f Fischbach I. Pakula T. Minkin P. Fechtenkotter A. Müllen K. Spiess HW. Saalwachter K. J. Phys. Chem. B  2002,  106:  6408 
  • 11 Gherghel L. Brand JD. Baumgarten M. Müllen K. J. Am. Chem. Soc.  1999,  121:  8104 
  • 12 Herwig PT. Enkelmann V. Schmelz O. Müllen K. Chem.-Eur. J.  2000,  6:  1834 
  • 14a Schunack M. Laegsgaard E. Stensgaard I. Johannsen I. Besenbacher F. Angew. Chem. Int. Ed.  2001,  40:  2623 
  • 14b Schunack M. Petersen L. Kuhnle A. Laegsgaard E. Stensgaard I. Johannsen I. Besenbacher F. Phys. Rev. Lett.  2001,  86:  456 
  • 15a Stabel A. Herwig P. Müllen K. Rabe JP. Angew. Chem., Int. Ed. Engl.  1995,  34:  1609 
  • 16a Possel O. Van Leusen AM. Tetrahedron Lett.  1977,  48:  4229 
  • 16b Van Leusen AM. Lect. Heterocyl. Chem.  1980,  5:  S111 
  • 17 Iyer VS. Wehmeier M. Brand JD. Keegstra MA. Müllen K. Angew. Chem. Int. Ed.  1997,  36:  1604 
  • 18a Mueller-Westerhoff UT. Zhou M. J. Org. Chem.  1994,  59:  4988 
  • 18b Okimoto M. Itoh T. Chiba T. J. Org. Chem.  1996,  61:  4835 
  • 19 John JA. Tour JM. J. Am. Chem. Soc.  1994,  116:  5011 
1

Present address: Chembiotek Research Pvt. Ltd, Block-Bn, Plot-7, Sector-V, Salt Lake Electronic Complex, Calcutta 700 091, India

13

Gimzewski, J. K., unpublished results