[en] The self-assembly of functional polythiophenes was studied by a bottom-up approach 'from molecule to polymer'. The synthesis and the X-ray structure of 2,5-dibromo-3-styryl and 3-2',3',4',5',6'-pentafluorostyryl-thiophenes revealed a supramolecular arrangement controlled by p-p interactions between the aromatic rings. A [2 + 2] photocyclization reaction in the solid state of (E)-1-2',5'-dibromo-3'-thienyl-2-pentafluorophenylethene triggers the formation of a rare cycloadduct comprising thiophene rings. The X-ray analysis confirmed its rctt stereochemistry. The synthesis of P3HT-b-P3ST and P3HT-b-P3STF block oligomers was achieved by a GRIM method in good yields. An indirect proof of well-defined nanostructured organization was provided by the partial photocyclization of pendant styryl moieties under UV irradiation.
Disciplines :
Chemistry Physics
Author, co-author :
Clement, Sebastien
Meyer, Franck
De Winter, Julien ; Université de Mons > Faculté des Sciences > Synthèse et spectrométrie de masse organiques
Coulembier, Olivier ; Université de Mons > Faculté des Sciences > Matériaux Polymères et Composites
Vande Velde, Christophe M. L.
Zeller, Matthias
Gerbaux, Pascal ; Université de Mons > Faculté des Sciences > Synthèse et spectrométrie de masse organiques
Balandier, Jean-Yves
Sergeyev, Sergey
Lazzaroni, Roberto ; Université de Mons > Faculté des Sciences > Service de Chimie des matériaux nouveaux
Geerts, Yves
Dubois, Philippe ; Université de Mons > Faculté des Sciences > Matériaux Polymères et Composites
Language :
English
Title :
Synthesis and Supramolecular Organization of Regioregular Polythiophene Block Oligomers
Publication date :
05 March 2010
Journal title :
Journal of Organic Chemistry
ISSN :
0022-3263
Publisher :
American Chemical Society, United States - District of Columbia
Volume :
75
Issue :
5
Pages :
1561-1568
Peer reviewed :
Peer Reviewed verified by ORBi
Research unit :
S816 - Matériaux Polymères et Composites S817 - Chimie des matériaux nouveaux S836 - Synthèse et spectrométrie de masse organiques
Research institute :
R400 - Institut de Recherche en Science et Ingénierie des Matériaux
a) Garcia, R.; Martinez, R. V.; Martinez, J. Chem. Soc. Rev. 2006, 35, 29-38.
b) Gratton, S. E. A.; Williams, S. S.; Napier, M. E.; Pohlhaus, P. D.; Zhou, Z.; Wiles, K. B.; Maynor, B. W.; Shen, C.; Olafsen, T.; Samulski, E. T.; DeSimone, J. M. Acc. Chem. Res. 2008, 41, 1685-1695.
c) Lim, Y.-B.; Lee, M. Angew. Chem., Int. Ed. 2009, 48, 2-6.
Lu, W.; Lieber, C. M. Nat. Mater. 2007, 6, 841-850.
a) McCullough, R. D.; Ewbank, P. C. Handbook of Conducting Polymers; Marcel Dekker: New York, 1997.
b) Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, 1999.
c) Osaka, I.; McCullough, R. D. Acc. Chem. Res. 2008, 41, 1202-1214.
b) McCulloch, I.; .Heeney, M.; Bailey, C.; Genevicius, K.; MacDonald, I.; Shkunov, M.; Sparrowe, D.; Tierney, S.; Wagner, R.; Zhang, W.; Chabinyc, M. L.; Kline, R. J.; McGehee, M. D.; Toney, M. F. Nat. Mater. 2006, 5, 328-333.
c) Yuen, J. D.; Dhoot, A. S.; Namdas, E. B.; Coates, N. E.; Heeney, M.; McCulloch, I.; Moses, D.; Heeger, A. J. J. Am. Chem. Soc, 2007, 129, 14367-14371.
d) Hamadani, B. H.; Gundlach. D. J.; McCulloch, I.; Heeney, M. Appl. Phys. Lett. 2007, 91, 243512.
e) Ohkita, H.; Cook, S.; Astuti, Y.; Duffy, W.; Tierney, S.; Zhang, W.; Heeney, M.; McCulloch, I.; Nelson, J.; Bradley, D. D. C.; Durrant, J. R. J. Am. Chem. Soc. 2008, 130, 3030-3042.
Wagner, P.; Ballantyne, A. M.; Jolley, K. W.; Officer, D. L. Tetrahedron 2006, 62, 2190-2199.
Nagarathinam, M.; Peedikakkal, A. M. P.; Vittal, J. J. Chem. Commun. 2008, 5277-5288.
Schmidt, G. M. J. Pure Appl. Chem, 1971, 27, 647-678.
Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433-481.
Vedernikov, A. I.; Kuzmina, L. G.; Tsazonov, S. K.; Lobova, N. A.; Loginov, P. S.; Churakov, A. V.; Strelenko, Y. A.; Howard, J. A. K.; Alfimov, M. V.; Gromov, S. P. Russ. Chem. Bull., Int. Ed. 2007, 56, 1860-1883.
Coates, G. W.; Dunn, A. R.; Henling, L. M.; Ziller, J. W.; Lobkovsky, E. B.; Grubbs, R. H. J. Am. Chem, Soc. 1998, 120, 3641-3649.
Nättinen, K. I.; Rissanen, K. Cryst. Growth Des. 2003, 3, 339-353.
Amato, M. E.; Musumarra, G.; Scarlata, G.; Lamba, D.; Spagna, R. J. Crystallogr. Spedrosc. Res. 1989, 19, 791-808.
Fernandez, G. E.; Perez, M.; Sanchez, L.; Martin, N. Angew. Chem., Int. Ed. 2008, 47, 1094-1097.
a) Yokozawa, T.; Adacli, I.; Miyakoshi, R.; Yokoyama, A. Hieh Perform. Polym. 2007, 19, 684-699.
b) Ohshimizu, K.; Ueda, M. Macromolecules 2008, 41, 5289-5294.
c) Zhang, Y.; Keisuke, T.; Kouske, H.; Kazuhito, H. J. Am. Chem. Soc. 2008, 130, 7812-7813.