Synthesis of a π-extended TTF-perylenediimide donor-acceptor dyad

Tetrahedron Letters

Volumn 49, Issue 20, 2008, Pages 3225-3228

  Gómez, Rafael ^a   Coya, Carmen ^b   Segura, José L ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD REY JUAN CARLOS   (Spain)

Author keywords

Extended tetrathiafulvalene; Electrochemistry; Fluorescence; Perylenediimide; Wittig reaction

Indexed keywords

IMIDE; PERYLENEDIIMIDE; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; FLUORESCENCE; PHOTOCHEMICAL QUENCHING; POTENTIOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 42149108418     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.091     Document Type: Article

References (48)

1. Gómez R., and Segura J.L. Handbook of Organic Electronics and Photonics Vol. 3 (2007), American Scientific
2. For reviews, see:. Segura J.L., Martín N., and Guldi D.M. Chem. Soc. Rev. 34 (2005) 31-47
3. Imahori H., Mori Y., and Matano Y. J. Photochem. Photobiol. C: Photochem. Rev. 4 (2003) 51-83
4. Gorgues A., Hudhomme P., and Sallé M. Chem. Rev. 104 (2004) 5151-5184
5. Zollinger H. Color Chemistry. 3rd ed. (2003), VCH, Weinheim
6. Herbst W., and Hunger K. Industrial Organic Pigments: Production, Properties, Applications. 2nd ed. (1997), Wiley-VCH, Weinheim Recent reviews on PDI chemistry
7. Würthner F. Chem. Commun. (2004) 1564-1579
8. Langhals H. Helv. Chim. Acta 88 (2005) 1309-1343
9. Gómez R., Veldman D., Blanco R., Seoane C., Segura J.L., and Janssen R.A.J. Macromolecules 40 (2007) 2760-2772
10. Blanco R., Gómez R., Segura J.L., Mena-Osteritz E., and Bäuerle P. Org. Lett. 9 (2007) 2171-2174
11. Segura J.L., Gómez R., Blanco R., Reinold E., and Bäuerle P. Chem. Mater. 18 (2006) 2834-2847
12. Segura J.L., Gómez R., Reinold E., and Bäuerle P. Org. Lett. 7 (2005) 2345-2348
13. Gómez R., Segura J.L., and Martín N. Org. Lett. 7 (2005) 717-720
14. Baffreau J., Perrin L., Leroy-Lhez S., and Hudhomme P. Tetrahedron Lett. 46 (2005) 4599-4603
15. Hua J., Meng F., Ding F., Li F., and Tian H. J. Mater. Chem. 14 (2004) 1849-1853
16. Beckers E.H.A., Meskers S.C.J., Schenning A.P.H.J., Chen Z., Würthner F., and Janssen R.A.J. J. Phys. Chem. A 108 (2004) 6933-6937
17. Beckers E.H.A., Chen Z., Meskers S.C.J., Jonkheijm P., Schenning A.P.H.J., Li X.-Q., Osswald P., Würthner F., and Janssen R.A.J. J. Phys. Chem. B 110 (2006) 16967-16978
18. Beckers E.H.A., Meskers S.C.J., Schenning A.P.H.J., Chen Z., Würthner F., Marsal P., Beljonne D., Cornil J., and Janssen R.A.J. J. Am. Chem. Soc. 128 (2006) 649-657
19. Kaletaş B.K., Dobrawa R., Sautter A., Würthner F., Zimine M., De Cola L., and Williams R. J. Phys. Chem. A 108 (2004) 1900-1909
20. You C.-C., Espindola P., Hippius C., Heinze J., and Würthner F. Adv. Funct. Mater. 17 (2007) 3764-3772
21. You C.-C., Saha-Möller C.R., and Würthner F. Chem. Commun. (2004) 2030
22. Cremer J., Mena-Osteritz E., Pschierer N.G., Müllen K., and Bäuerle P. Org. Biomol. Chem. 3 (2005) 985
23. Jiménez A.J., Spanig F., Rodríguez-Morgade M.S., Ohkubo K., Fukuzumi S., Guldi D.M., and Torres T. Org. Lett. 9 (2007) 2481-2484
24. Prodi A., Chiorboli C., Scandola F., Iengo E., Alessio E., Dobrawa R., and Würthner F. J. Am. Chem. Soc. 127 (2005) 1454-1462
25. Van der Boom T., Hayes R.T., Zhao Y., Bushard P.J., Weiss E.A., and Wasielewski M.R. J. Am. Chem. Soc. 124 (2002) 9582-9590
26. Leroy-Lehz S., Baffreau J., Perrin L., Levillain E., Allain M., Blesa M.-J., and Hudhomme P. J. Org. Chem. 70 (2005) 6313-6320
27. Leroy-Lhez S., Perrin L., Baffreau J., and Hudhomme P. C. R. Chemie (2006) 240-246
28. Schmidt-Mencke L., Fechtenkötter A., Müllen K., Moons E., Friend R.H., and MacKenzie J.D. Science 293 (2001) 1119
29. Edvinsson T., Li C., Pschirer N., Schöneboom J., Eickemeyer F., Sens R., Boschloo G., Herrmann A., Müllen K., and Hagfeldt A. J. Phys. Chem. C 111 (2007) 15137-15140
30. You C.-C., Hippius C., Grüne M., and Würthner F. Chem. Eur. J. 12 (2006) 7510-7519
31. Flamigni L., Ventura B., You C.-C., Hippius C., and Würthner F. J. Phys. Chem. C 111 (2007) 622-630
32. Sautter A., Kaletaş B.K., Schmid D.G., Dobrawa R., Zimine M., Jung G., van Stokkum I.H.M., De Cola L., Williams R.M., and Würthner F. J. Am. Chem. Soc. 127 (2005) 6719-6729
33. For reviews on TTF chemistry and applications, see:. Segura J.L., and Martín N. Angew. Chem., Int. Ed. 40 (2001) 1372-1409
34. Bendikov M., Wudl F., and Perepichka D.F. Chem. Rev. 104 (2004) 4891-4946
35. Nielsen M.B., Lomholt C., and Becher J. Chem. Soc. Rev. 29 (2000) 153-164
36. Martín N., Sánchez L., Herranz M.A., Illescas B., and Guldi D.M. Acc. Chem. Res. 40 (2007) 1015-1024
37. Giacalone F., Segura J.L., Martín N., and Guldi D.M. J. Am. Chem. Soc. 126 (2006) 5340-5341
38. Guldi D.M., Giacalone F., de la Torre G., Segura J.L., and Martín N. Chem. Eur. J. 11 (2005) 7199-7210
39. Giacalone F., Segura J.L., Martín N., Raney J., and Guldi D.M. Chem. Eur. J. 11 (2005) 4819-4834
40. Otero M., Herranz M.A., Seoane C., Martín N., Garín J., Orduna J., Alcalá R., and Villacampa B. Tetrahedron 58 (2002) 7463-7475
41. Langhals H., and Saulich S. Chem. Eur. J. 8 (2002) 5630-5643
42. Drefahl G., and Plötner G. Chem. Ber. 94 (1961) 907-914
43. 4: C: 74.55 H, 5.34, N, 2.56. Found: C, 74.72, H, 5.18, N, 2.52.
44. Salbeck J., Kunkely H., Langhals H., Saalfrank R.W., and Daub J. Chimia 43 (1989) 6-9
45. Liu S.-G., Pérez I., Martín N., and Echegoyen L. J. Org. Chem. 65 (2000) 9092-9102
46. Langhals H., Demmig S., and Huber H. Spectrochim. Acta 44A (1998) 1189-1193
47. Value corresponding to the peak of lowest energy featured in the emission spectra.
48. cc (18.1 Å) were estimated by semiempirical PM3 calculations. The radius of the PDI anion (4.7 Å) was estimated from the density of N,N′-dimethylperylene-3,4:9,10-tetracarboxylic diimide determined from the X-ray crystallographic data (Hádicke, E.; Graser, F. Acta Crystallogr., Sect. C 1986, 42, 189-195)