Synthesis and physical properties of polyfluoro-acridines bearing perfluoroalkyl chains

Journal of Fluorine Chemistry

Volumn 129, Issue 4, 2008, Pages 294-300

  Papagni, Antonio ^a   Campiglio, Paolo ^a   Campione, Marcello ^a   Del Buttero, Paola ^b   Mani, Antonio ^a   Miozzo, Luciano ^a   Tonelli, Enrico ^a  

^a UNIVERSITY OF MILANO BICOCCA   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

Perfluoro alkyl chain; Phase contrast AFM; Surface segregation; Tetrafluoro acridine

Indexed keywords

EID: 40649087310     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.01.005     Document Type: Article

References (16)

1. Facchetti A., Deng Y., Wang A., Koide Y., Sirringhaus H., Marks T.J., and Friend R.H. Angew. Chem. Int. Ed. 112 (2000) 4721-4725
2. Facchetti A., Mushrush M., Katz H.E., and Marks T.J. Adv. Mater. 15 (2003) 33-38
3. Ebbens S.J., and Badyal J.P.S. Langmuir 17 (2001) 4050-4055
4. Schaub T.K., Kellogg G.J., and Mayes A.M. Macromolecules 29 (1996) 3982-3990
5. Iyengar D.R., Perutz S.M., Dai C., Ober C.K., and Kramer E.J. Macromolecules 29 (1996) 1229-1234
6. Würthner F. Angew. Chem. Int. Ed. 40 (2001) 1037-1039
7. Papagni A., Del Buttero P., Moret M., Sassella A., Miozzo L., and Ridolfi G. Chem. Mater. 15 (2003) 5010-5018
8. Giovanella U., Botta C., Papagni A., Tubino R., and Miozzo L. Appl. Phys. Lett. 87 (2005) 171910(1-3)
9. While 2-methoxy-aniline gives the expected tetrafluoro-acridine with a fairy good yield, both 2-bromo-aniline and 2 thiomethoxy-aniline did not give the desired tetrafluoro-acridine, even when reacted under forcing condition (200 °C). These findings can be explained in terms of sterical hindrance, indeed the V.d.W radii of Br and S are significantly higher (1.85 Å for Br and 1.80 Å for S vs. 1.52 Å for O).
10. M.J. Robson, Eur. Pat. Appl., EP 271240, A2 19880615 (1988).
11. Gerasimova T.N., Gelumbovskaya L.L., and Fokin E.P. Izvestiya Sibirskogo Otdeleniya Akademii Nauk SSSR, Seriya Khimicheskikh Nauk 2 (1973) 96-100
12. Orlova N.A., Burov D.M., Gerasimova T.N., and Fokin E.P. Izvestiya Sibirskogo Otdeleniya Akademii Nauk SSSR, Seriya Khimicheskikh Nauk 2 (1984) 115-118
13. Orlova N.A., Burov D.M., Gerasimova T.N., and Fokin E.P. Izvestiya Sibirskogo Otdeleniya Akademii Nauk SSSR, Seriya Khimicheskikh Nauk 1 (1984) 115-118
14. Miozzo L., Papagni A., Casalbore-Miceli G., Del Buttero P., Girotti C., Moret M., and Trabattoni S. Chem. Mater. 16 (2004) 5124-5132
15. Bäuerle P., Würthner F., and Heid S. Angew. Chem. Int. Ed. 29 (1990) 419-420
16. Maganov S.N., Elings V., and Whangbo M.-H. Surf. Sci. 375 (1997) L385-L391