Highly fluorescent oligothiophenes through the incorporation of central dithieno[3,2-b:2′,3′-d]pyrrole units

Organic Letters

Volumn 7, Issue 23, 2005, Pages 5253-5256

  Radke, Karla R ^a   Ogawa, Katsu ^a   Rasmussen, Seth C ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28244442163     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052152a     Document Type: Article

References (31)

1. Semiconducting Polymers: Chemistry, Physics and Engineering; Hadziioannou, G., van Hutten, P. F., Eds.; Wiley-VCH: Weinheim, 2000.
2. Roncali, J. Chem. Rev. 1992, 92, 711.
3. Roncali, J. In Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998; Chapter 12.
4. Rasmussen, S. C.; Straw, B. D.; Hutchison, J. E. In Semiconducting Polymers: Applications, Synthesis, and Properties; Hsieh, B. R., Wei, Y.; Galvin, M., Eds.; ACS Symposium Series 735; American Chemical Society: Washington, DC, 1999; Chapter 21.
5. Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, 1999.
6. Zhang, X.; Matzger, A. J. J. Org. Chem. 2003, 68, 9813.
7. Laquindanum, J. G.; Katz, H. E.; Lovinger, A. J. J. Am. Chem. Soc. 1998, 120, 664.
8. Bao, Z. Adv. Mater. 2000, 12, 227.
9. Barbarella, G.; Favaretto, L.; Sotgiu, G.; Zambianchi, M.; Fattori, V.; Cocchi, M.; Cacialli, F.; Gigli, G.; Cingolani, R. Adv. Mater. 1999, 11, 1375.
10. (a) Mitschke U.; Bäuerle, P. J. Chem. Soc., Perkin Trans. 1 2001, 740.
11. (b) Mitschke, U.; Mena Osteritz, E.; Debaerdemaeker, T.; Sokolowski, M.; Bäuerle, P. Chem. Eur. J. 1998, 4, 2211.
12. Noma, N.; Tsuzuki, T.; Shirota, Y. Adv. Mater. 1995, 7, 647.
13. Dediu, V.; Murgia, M.; Matacotta, F. C.; Taliani, C.; Barbanera, S. Solid State Commun. 2002, 122, 181.
14. Cerminara, M.; Meinardi, F.; Borghesi, A.; Sassella, A.; Tubino, R. Thin Solid Films 2005, 474, 230.
15. Ogawa, K.; Rasmussen, S. C. J. Org. Chem. 2003, 68, 2921.
16. Ogawa, K.; Stafford, J. A.; Rothstein, S. D.; Tallman, D. E.; Rasmussen, S. C. Synth. Met. 2005, 152, 137.
17. (a) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
18. (b) Lukevics, E.; Arsenyan, P.; Pudova, O. Heterocycles 2003, 60, 663.
19. Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, 2nd ed.; Pergamon: New York, 2000; pp 320-321.
20. With the exception of the thiazole analogues, which gave lower yields presumably due to the lower reactivity of the bromothiazole reagent.
21. (a) Becker, R. S.; de Melo, J. S.; Macanita, A. L.; Elisei, F. Pure Appl. Chem. 1995, 67, 9.
22. (b) Becker, R. S.; de Melo, J. S.; Macanita, A. L.; Elisei, F. J. Phys. Chem. 1996, 100, 18683.
23. Berlman, I. B. J. Phys. Chem. 1970, 74, 3085.
24. Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, 2nd ed.; Pergamon: New York, 2000; pp 68-71.
25. Takayanagi, M.; Gejo, T.; Hanazaki, I. J. Phys. Chem. 1994, 98, 12893.
26. de Melo, J. S.; Burrows, H. D.; Svensson, M.; Andersson, M. R.; Monkman, A. P. J. Chem. Phys. 2003, 118, 1550.
27. Xu, B.; Holdcroft, S. Macromolecules 1993, 26, 4457.
28. Benincori, T.; Bongiovanni, G.; Botta, C.; Cerullo, G.; Lanzani, G.; Mura, A.; Rossi, L.; Sannicolo, F.; Tubino, R. Phys. Rev. B 1998, 58, 9082.
29. (a) Pasini, M.; Destri, S.; Botta, C.; Porzio, W. Tetrahedron 1999, 55, 14985.
30. (b) Pasini, M.; Destri, S.; Botta, C.; Porzio, W. Synth. Met. 2000, 113, 129.
31. Theander, M.; Inganäs, O.; Mammo, W.; Olinga, T.; Svensson, M.; Andersson, M. R. J. Phys. Chem. B 1999, 103, 771.