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Synthesis 2010(7): 1123-1140
DOI: 10.1055/s-0029-1218667
DOI: 10.1055/s-0029-1218667
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Hexa-peri-hexobenzocoronenes Carrying Linear or Branched Perfluoroalkylated Side Chains
Further Information
Received
23 November 2009
Publication Date:
05 February 2010 (online)
Publication History
Publication Date:
05 February 2010 (online)
Abstract
Substituted disc-shaped perfluoroalkylated hexa-peri-hexabenzocoronenes (HBC), known to self-assemble into conducting ordered architectures, were synthesized and characterized. A systematic variation of the linear or branched perfluoroalkylated side chains was performed in order to screen the influence of the lateral chain on their one-dimensional self-aggregation.
Key words
HBC - perfluoroalkylated substitutions - cross-coupling - cyclodehydrogenation - tandem Sonogashira
- 1
Whitesides GM.Mathias JP.Seto CT. Science 1991, 254: 1312 -
2a
Cubberley MS.Iverson BL. J. Am. Chem. Soc. 2001, 123: 7560 -
2b
Claessens CG.Stoddart JF. J. Phys. Org. Chem. 1997, 10: 254 -
3a
Dewa T.Endo K.Aoyama Y. J. Am. Chem. Soc. 1998, 120: 8933 -
3b
Prins LJ.Reinhoudt DN.Timmerman P. Angew. Chem. Int. Ed. 2001, 40: 2382 -
3c
Gearba RI.Lehmann M.Levin J.Ivanov DA.Koch MHJ.Barbera J.Debije MG.Piris J.Geerts YH. Adv. Mater. 2003, 15: 1614 - 4
Kolotuchin SV.Zimmerman SC. J. Am. Chem. Soc. 1998, 120: 9092 - 5
Gorman C. Adv. Mater. 1998, 10: 295 -
6a
Chandrasekhar S.Sadashiva BK.Suresh KA. Pramana 1977, 471 -
6b
Tschierske C. J. Mater. Chem. 2001, 11: 2647 -
7a
Förster S.Plantenberg T. Angew. Chem. Int. Ed. 2002, 41: 688 -
7b
Förster S.Antonietti M. Adv. Mater. 1998, 10: 195 -
8a
Brunsveld L.Folmer BJB.Meijer EW.Sijbesma RP. Chem. Rev. 2001, 101: 4071 -
8b
Zeng F.Zimmerman SC. Chem. Rev. 1997, 97: 1681 -
9a
Cui Y.Lee SJ.Lin W. J. Am. Chem. Soc. 2003, 125: 6014 -
9b
Kaes C.Hosseini MW.Rickard CEF.Skelton BW.White AH. Angew. Chem. Int. Ed. 1998, 37: 920 -
9c
Hennigar TL.MacQuarrie DC.Losier P.Rogers RD.Zaworotko MJ. Angew. Chem. Int. Ed. 1997, 36: 972 -
10a
Dötz F.Brand JD.Ito S.Gherghel L.Müllen K. J. Am. Chem. Soc. 2000, 122: 7707 -
10b
Kumar S. Liq. Cryst. 2005, 32: 1089 -
10c
Hara T.Furukawa K.Nakamura T.Yamamoto Y.Kosaka A.Jin W.Fukushima T.Aida T. J. Phys. Soc. Jpn. 2008, 77: 034710 -
11a
van de Craats AM.Warman JM. Adv. Mater. 2001, 13: 130 -
11b
van de Craats AM.Warman JM.Fechtenkötter A.Brand JD.Harbison MA.Müllen K. Adv. Mater. 1999, 11: 1469 -
12a
Aebischer OF.Aebischer A.Tondo P.Alameddine B.Dadras M.Güdel H.-U.Jenny TA. Chem. Commun. 2007, 4221 -
12b
Aebischer OF.Aebischer A.Donnio B.Alameddine B.Dadras M.Güdel H.-U.Guillon D.Jenny TA. J. Mater. Chem. 2007, 17: 1262 -
12c
Aebischer OF.Alameddine B.Jenny TA. Chimia 2008, 62: 967 - 13
Kovacic P.Jones MB. Chem. Rev. 1987, 87: 357 - 14
Alameddine B.Aebischer OF.Amrein W.Donnio B.Deschenaux R.Guillon D.Savary C.Scanu D.Scheidegger O.Jenny TA. Chem. Mater. 2005, 17: 4798 -
15a
Fechtenkötter A.Tchebotareva N.Watson M.Müllen K. Tetrahedron 2001, 57: 3769 -
15b
Pisula W.Kastler M.Wasserfallen D.Pakula T.Müllen K. J. Am. Chem. Soc. 2004, 126: 8074 -
15c
Wu J.Watson MD.Zhang L.Wang Z.Müllen K. J. Am. Chem. Soc. 2004, 126: 177 -
16a
Vollhardt KP. Angew. Chem., Int. Ed. Engl. 1984, 23: 539 -
16b
Vollhardt KP. Acc. Chem. Res. 1977, 10: 1 -
16c
Funk RL.Vollhardt KP. J. Am. Chem. Soc. 1980, 102: 5253 - 17
Feng X.Wu J.Enkelmann V.Müllen K. Org. Lett. 2006, 8: 1145 - 18
Mio MJ.Kopel LC.Braun JB.Gadzikwa RL.Hull KL.Brisbois RG.Markworth CJ.Grieco PA. Org. Lett. 2002, 4: 3199 - 19
Soós T.Bennett BL.Rutherford D.Barthel-Rosa LP.Gladysz JA. Organometallics 2001, 20: 3079 -
20a
Gambaretto G.Conte L.Fornasieri G.Zarantonello C.Tonei D.Sassi A.Bertani R. J. Fluorine Chem. 2003, 121: 57 -
20b
Améduri B.Boutevin B.Nouiri M.Talbi M. J. Fluorine Chem. 1995, 74: 191 -
20c
Johansson G.Percec V.Ungar U.Zhou JP. Macromolecules 1996, 29: 646 -
21a
Darses S.Pucheault M.Genêt J.-P. Eur. J. Org. Chem. 2001, 1121 -
21b
Darses S.Michaud G.Genêt J.-P. Eur. J. Org. Chem. 1999, 1875 - 22
Yang SH.Li CS.Cheng CH. J. Org. Chem. 1987, 52: 691 -
23a
Mazerolles P.Boussaguet P.Huc V. Org. Synth. 1999, 76: 221 -
23b
Tamura M.Kochi J. J. Am. Chem. Soc. 1971, 93: 1485 -
24a
Quiclet-Sire B.Zard SZ. J. Am. Chem. Soc. 1996, 118: 9190 -
24b
Boivin J.Quiclet-Sire B.Ramos L.Zard SZ. Chem. Commun. 1997, 353 - 25
Li Y.Hesse M. Helv. Chim. Acta 2003, 86: 310 - 26
Toshiyuki T,Katsutake T,Atsuhiro H,Satoko F, andToshiyuki K. inventors; JP 2006131553. - 27
Aebischer OF.Tondo P.Alameddine B.Jenny TA. Synthesis 2006, 2981 -
28a
G uittard F.Geribaldi S. J. Fluorine Chem. 2001, 107: 363 -
28b
Visjager J.Tervoort TA.Smith P. Polymer 1999, 40: 4533 -
28c
Turberg MP.Brady JE. J. Am. Chem. Soc. 1988, 110: 7797 -
29a
Fechtenkötter A.Tchebotareva N.Watson M.Müllen K. Tetrahedron 2001, 57: 3769 -
29b
Hayashi T.Konishi M.Kobori Y.Kumada M.Higuchi T.Hirotsu K. J. Am. Chem. Soc. 1984, 106: 158 -
30a
Viciu MS.Kissling RM.Stevens ED.Nolan SP. Org. Lett. 2002, 4: 2229 -
30b
Lebel H.Janes MK.Charette AB.Nolan SP. J. Am. Chem. Soc. 2004, 126: 5046 -
30c
Huang J.Nolan SP. J. Am. Chem. Soc. 1999, 121: 9889 - 31
Pardo J.Cobas A.Guitián E.Castello L. Org. Lett. 2001, 3: 3711 - 32
Muñoz D. Master’s Thesis University of Fribourg; Switzerland: 2007. - 33
Maruoka K.Sano H.Shinoda K. J. Am. Chem. Soc. 1986, 108: 6036 - 34
Kastler M.Pisula W.Wasserfallen D.Pakula R.Müllen K. J. Am. Chem. Soc. 2005, 127: 4286 - 35
Pangborn MB.Giardello MA.Grubbs RH.Rosen RK.Timmers FJ. Organometallics 1996, 15: 1518