RSS-Feed abonnieren
DOI: 10.1055/s-2003-44996
Synthesis and Properties of Monosubstituted Ethynylcorannulenes
Publikationsverlauf
Publikationsdatum:
17. Dezember 2003 (online)
![](https://www.thieme-connect.de/media/synlett/200401/lookinside/thumbnails/10.1055-s-2003-44996-1.jpg)
Abstract
The solution-phase synthesis of corannulene has been modified and it is now possible to prepare multi gram quantities of corannulene more efficiently, with considerably less toxic reagents. Cross-coupling of bromocorannulene with TMS-acetylene and phenylacetylene affords novel ethynyl-containing corannulene derivatives. Deprotection of TMS-ethynyl corannulene affords the naked alkyne, which can be cross-coupled with pentafluoroiodobenzene and bromocorannulene to afford the appropriate alkyne derivatives. The photophysical properties of this new and novel family of alkyne-containing corannulene derivatives has been evaluated and all of the new derivatives exhibit low to moderate quantum efficiencies.
Key words
fullerene - corannulene - alkynes - PAH - cross-coupling
-
3a
Siegel JS.Seiders TJ. Chem. Br. 1995, 313 -
3b
Rabideau PW.Sygula A. In Advances in Theoretically Interesting Molecules Vol. 3:Thummel RP. Jai Press Inc.; Conneticut: 1995. p.1-36 -
3c
Rabideau PW.Sygula A. Acc. Chem. Res. 1996, 29: 235 -
3d
Scott LT. Pure Appl. Chem. 1996, 68: 291 - 4
Barth WE.Lawton RG. J. Am. Chem. Soc. 1966, 88: 380 -
5a
Sieders TJ.Elliott EL.Grube G.Siegel JS. J. Am. Chem. Soc. 1999, 121: 7804 -
5b
Scott LT. Pure Appl. Chem. 1996, 68: 291 -
5c
Cheng P.-C. PhD Dissertation University; Boston: 1996. p.212 -
6a
Grube GH.Elliott EL.Steffens RJ.Jones CS.Baldridge KK.Siegel JS. Org. Lett. 2003, 5: 713 -
6b
Metal-Catalyzed Cross-Coupling Reactions
Diederich FN.Stang PJ. Wiley-VCH; : . -
6c
Tsuji J. Palladium Reagents and Catalysts, Innovations in Organic Synthesis Wiley; New York: 1995. -
7a
Eberhard MR.Wang Z.Jensen CM. Chem. Commun. 2002, 818 -
7b
Morales-Morales D.Grause C.Kasaok K.Redon R.Cramer RE.Jensen CM. Inorg. Chim. Acta. 2000, 300-302: 958 -
8a
Sonagashira K.Toda Y.Hagihara N. Tetrahedron Lett. 1975, 4467 -
8b For a recent highlight see:
Tykwinski RR. Angew. Chem. Int. Ed. 2003, 42: 1566 -
9a
Anastasia L.Negishi E. Org. Lett. 2001, 3: 3111 -
9b
Yang C.Nolan SP. Organometallics 2002, 21: 1020 -
9c
Plenio H.Hermann J.Sehring A. Chem.-Eur. J. 2000, 6: 1820 -
9d
Alami M.Crousse B.Ferri FJ. Organomet. Chem. 2001, 624: 114 -
9e
Batey RA.Shen M.Lough A. J. Org. Lett. 2002, 4: 1411 -
10a
Scott LT.Hashemi MM.Meyer DT.Warren HB. J. Am. Chem. Soc. 1991, 113: 7082 -
10b
Scott LT.Hashemi MM.Bratcher MS. J. Am. Chem. Soc. 1992, 114: 1920 -
10c
Scott LT.Cheng P.-C.Hashemi MM.Bratcher MS.Meyer DT.Warren HB. J. Am. Chem. Soc. 1997, 119: 10963 - 11
Sygula A.Rabideau PW. J. Am. Chem. Soc. 1999, 121: 7800 -
12a
Williams JK.Cockcroft JK.Fitch AN. Angew. Chem., Int. Ed. Engl. 1992, 104: 1666 -
12b
Williams JK.Cockcroft JK.Fitch AN. Angew. Chem., Int. Ed. Engl. 1992, 31: 1655 -
12c
Cozzi F.Siegel JS. Pure Appl. Chem. 1995, 67: 683 -
12d
Ponzini F.Zagha R.Hardcastle K.Siegel JS. Angew. Chem. Int. Ed. 2000, 39: 2323 -
12e
Nishinaga T.Nodera N.Miyata Y.Komatsu K. J. Org. Chem. 2002, 67: 6091 -
13a
Coates GW.Dunn AR.Henling LM.Dougherty DA.Grubbs RH. Angew. Chem., Int. Ed. Engl. 1997, 36: 248 -
13b
Coates GW.Dunn AR.Henling LM.Ziller JW.Lobkovsky EB.Grubbs RH. J. Am. Chem. Soc. 1998, 120: 3641 -
13c
Weck M.Dunn AR.Matsumoto K.Coates GW.Lobkovsky EB.Grubbs RH. Angew. Chem. Int. Ed. 1999, 38: 2741 -
14a
Steed JM.Dixon TA.Klemperer W. J. Chem. Phys. 1979, 70: 4940 -
14b
Claessens M.Palombini L.Stein M.-L.Reisse J. New. J. Chem. 1982, 6: 595 -
14c
Almlöf J.Faegri K. J. Chem. Phys. 1983, 79: 2284 -
14d
Laidig KE. Chem. Phys. Lett. 1991, 185: 483 - 15
Desiraju GR. Angew. Chem., Int. Ed. Engl. 1995, 34: 2311 -
16a
Verdieck JF.Jankowski WA. Mol. Lumin. Int. Conf. 1969, 829 -
16b
Argentine SM.Francis AH.Chen C.-C.Lieber CM.Siegel JS. J. Phys. Chem. 1994, 98: 7350 - 17
Rabideau PW.Abdourazak AH.Sygula R.Warner IM. J. Fluoresc. 1997, 7: 231 - 18
Demas JN.Crosby GA. J. Phys Chem. 1971, 75: 991 -
19a
Hamai S.Hirayama F. J. Phys. Chem. 1983, 87: 83 -
19b
Meech SR.Phillips D. J. Photochem. 1983, 23: 193 - 20
Borchardt A.Hardcastle K.Gantzel P.Siegel JS. Tetrahedron Lett. 1993, 34: 273
References
Department of Chemistry, University of Oregon, Eugene, OR 97403-1253.
2For correspondence use Zürich address.