Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2012(7): 1126-1130
DOI: 10.1055/s-0031-1289739
DOI: 10.1055/s-0031-1289739
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Dimerization of Monobenzoylated Monopyrrolotetrathiafulvalene
Further Information
Received
9 January 2012
Publication Date:
08 March 2012 (online)
Publication History
Publication Date:
08 March 2012 (online)
Abstract
Introduction of one benzoyl functional group into the 4-position of monopyrrolotetrathiafulvalene (MPTTF) affords MPTTF derivatives incorporating one hydrogen-bonding donor and one acceptor. This results in dimerization of the MPTTF derivatives in solution and in the solid state.
Key words
tetrathiafulvalene - functionalization - benzoylation - dimerization - pyrroles
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Canevet D.Sallé M.Zhang G.Zhang D.Zhub D. Chem. Commun. 2009, 2245 -
1b
Segura JL.Martín N. Angew. Chem. Int. Ed. 2001, 40: 1372 ; Angew. Chem. 2001, 113, 1416 -
1c
Becher J.Jeppesen JO.Nielsen K. Synth. Met. 2003, 133-134: 309 -
1d
Bryce MR. J. Mater. Chem. 2000, 10: 589 -
1e
Schukat G.Fanghänel E. Sulfur Rep. 1996, 18: 1 - 2
Ferraris J.Cowan DO.Walatka VV.Perlstein JH. J. Am. Chem. Soc. 1973, 95: 948 -
3a
Jérome D.Mazaud A.Ribault M.Bechgaard K. J. Phys. Lett. 1980, 41: L95 -
3b
Jérome D. Chem. Rev. 2004, 104: 5565 -
4a
Nielsen KA.Bähring S.Jeppesen JO. Chem. Eur. J. 2011, 17: 11001 -
4b
Park JS.Derf FL.Bejger CM.Lynch VM.Sessler JL.Nielsen KA.Johnsen C.Jeppesen JO. Chem. Eur. J. 2010, 16: 848 -
4c
Nielsen KA.Cho W.-S.Sarova GH.Petersen BM.Bond AD.Becher J.Jensen F.Guldi DM.Sessler JL.Jeppesen JO. Angew. Chem. Int. Ed. 2006, 45: 6848 ; Angew. Chem. 2006, 118, 7002 -
4d
Nielsen KA.Cho W.-S.Lyskawa J.Levillain E.Lynch VM.Sessler JL.Jeppesen JO. J. Am. Chem. Soc. 2006, 128: 2444 -
4e
Nielsen KA.Cho W.-S.Jeppesen JO.Lynch VM.Becher J.Sessler JL. J. Am. Chem. Soc. 2004, 126: 16296 -
5a
Jeppesen JO.Perkins J.Becher J.Stoddart JF. Angew. Chem. Int. Ed. 2001, 40: 1216 ; Angew. Chem. 2001, 113, 1256 -
5b
Jeppesen JO.Nielsen KA.Perkins J.Vignon SA.Di Fabio A.Ballardini R.Gandolfi MT.Venturi M.Balzani V.Becher J.Stoddart JF. Chem. Eur. J. 2003, 9: 2982 -
5c
Nygaard S.Leung KC.-F.Aprahamian I.Ikeda T.Saha S.Laursen BW.Kim S.-Y.Hansen SW.Stein PC.Flood AH.Stoddart JF.Jeppesen JO. J. Am. Chem. Soc. 2007, 129: 960 -
6a
Collier CP.Mattersteig G.Wong EW.Lou Y.Beverly K.Sampaio J.Raymo FM.Stoddart JF.Heath JR. Science 2000, 289: 1172 -
6b
Luo Y.Collier CP.Jeppesen JO.Nielsen KA.Delonno E.Ho G.Perkins J.Tseng H.-R.Yamamoto T.Stoddart JF.Heath JR. ChemPhysChem 2002, 3: 519 -
6c
Flood AH.Stoddart JF.Steuerman DW.Heath JR. Science 2004, 306: 2055 -
6d
Green E.Choi JW.Boukai A.Bunimovich Y.Johnston-Halperin E.Delonno E.Luo Y.Sheriff BA.Xu K.Shin YS.Tseng H.-R.Stoddart JF.Heath JR. Nature 2007, 445: 414 - 7
Jeppesen JO.Takimiya K.Jensen F.Brimert T.Nielsen K.Thorup N.Becher J. J. Org. Chem. 2000, 65: 5794 -
8a
Cho W.-S.Kim HJ.Littler BJ.Miller MA.Lee C.-H.Lindsey JS. J. Org. Chem. 1999, 64: 7890 -
8b
Lee C.-H.Li F.Iwamoto K.Dadok J.Bothner-By AA.Lindsey JS. Tetrahedron 1995, 51: 11645 - 9
Perrin DD.Armarego WLF. Purification of Laboratory Chemicals Pergamon Press; New York: 1988. - 10
Gottlieb HE.Kotlyar V.Nudelman A. J. Org. Chem. 1997, 62: 7512
References
CCDC 861255 (4b) and CCDC 861256 (5a) contain the supplementary crystallographic data for compounds described in this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac.uk].