Push-pull-substituted oligo(2,5-thienyleneethynylene)s

Synthesis

Volumn , Issue 6, 2006, Pages 1009-1015

  Mühling, Bastian ^a   Theisinger, Sonja ^a   Meier, Herbert ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Alkynes; Conjugation; Coupling; Heterocycles; Sulfur

Indexed keywords

OLIGOMERS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALKYNES; CONJUGATION; COUPLING; HETEROCYCLES;

OLEFINS;

2 BUTYLTHIO 5 ETHYNYLTHIOPHENE; GLYCERYL TRINITRATE; OLIGO(2,5 THIENYLENEETHYNYLENE DERIVATIVE); OLIGOMER; POLY(2,5 THIENYLENEETHYNYLENE DERIVATIVE); THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SONOGASHIRA REACTION; SYNTHESIS;

EID: 33645332084     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926348     Document Type: Article

References (31)

1. (a) Meier, H. Angew. Chem. Int. Ed. 2005, 44, 2482;
2. Angew. Chem. 2005, 117, 2536; and references cited therein.
3. (b) Martin, R. E.; Diederich, F. Angew. Chem. Int. Ed. 1999, 38, 1350;
4. Angew. Chem. 1999, 111, 1440.
5. (c) Electronic Materials: The Oligomer Approach; Müllen, K.; Wegner, G., Eds.; Wiley-VCH: Weinheim, 1998.
6. Ringenbach, C.; De Nicola, A.; Ziessel, R. J. Org. Chem. 2003, 68, 4708.
7. De Nicola, A.; Ringenbach, C.; Ziessel, R. Tetrahedron Lett. 2003, 44, 183.
8. Obara, Y.; Takimiya, K.; Aso, Y.; Otsubo, T. Tetrahedron Lett. 2001, 42, 6877.
9. Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906.
10. Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376.
11. Fujitsuka, M.; Makinoshima, T.; Ito, O.; Obara, Y.; Aso, T.; Otsubo, T. J. Phys. Chem. B 2003, 107, 739.
12. Li, J.; Liao, L.; Pang, Y. Tetrahedron Lett. 2002, 43, 391.
13. Pearson, D. L.; Jones, L. II; Schumm, J. S.; Tour, J. M. Synth. Met. 1997, 84, 303.
14. Samuel, I. D. W.; Ledoux, I.; Delporte, C.; Pearson, D. L.; Tour, J. M. Chem. Mater. 1996, 8, 819.
15. Geisler, T.; Petersen, J. C.; Bjoernholm, T.; Fischer, E.; Larsen, J.; Dehn, C.; Brédas, J.-L.; Tormos, G. V.; Nugara, P. N.; Lakshikantham, M. V.; Cava, M. P. Synth. Met. 1993, 53, 271.
16. Pearson, D. L.; Schumm, J. S.; Tour, J. M. Macromolecules 1994, 27, 2348.
17. Tormos, G. V.; Nugara, P. N.; Lakshikantham, M. V.; Cava, M. P. Synth. Met. 1993, 53, 271.
18. Carpita, A.; Lessi, A.; Rossi, R. Synthesis 1984, 571.
19. Bunz, U. H. F. Chem. Rev. 2000, 100, 1605; and references cited therein.
20. (a) Higgins, R. W.; Garrett, R. J. Org. Chem. 1961, 27, 2168.
21. (b) Jones, E.; Moodie, I. M. Tetrahedron 1965, 21, 2413.
22. (c) Gronowitz, S. Arkiv Kemi 1958, 13, 269;
23. Chem. Abstr. 1959, 53, 15056e.
24. HMQC and HMBC contour plots for 14a are depicted in: Hesse, M.; Meier, H.; Zeeh, B. Spektroskopische Methoden in der organischen Chemie, 7th ed.; Thieme: Stuttgart, 2005, 193.
25. Meier, H.; Gerold, J.; Kolshorn, H.; Mühling, B. Chem. Eur. J. 2004, 10, 360.
26. Meier, H.; Mühling, B.; Kolshorn, H. Eur. J. Org. Chem. 2004, 1033.
27. Mühling, B. Ph.D. Dissertation; University of Mainz: Germany, 2004.
28. Meier, H.; Stalmach, U.; Kolshorn, H. Acta Polym. 1997, 48, 379.
29. Ickenroth, D.; Weissmann, S.; Rumpf, N.; Meier, H. Eur. J. Org. Chem. 2002, 2808.
30. Raber, D. J. J. Am. Chem. Soc. 1971, 93, 4821.
31. Meier, H.; Mühling, B.; Oehlhof, A.; Theisinger, S.; Kirsten, E. Eur. J. Org. Chem. 2006, 405.