Bulletin of the Chemical Society of Japan p. 2141 - 2144 (1992)
Update date:2022-08-04
Topics:
Yoshino, Norio
Kitamura, Mitsuharu
Seto, Tsuyoshi
Shibata, Yasuhiro
Abe, Masahiko
Ogino, Keizo
The compounds, 4-(nonafluorobutyl)aniline, 4-(tridecafluorohexyl)aniline, and 4-(heptadecafluorooctyl)aniline were prepared by the reaction of corresponding perfluoroalkyl iodide with 4-iodoaniline in the presence of copper bronze.Six azobenzene derivatives (4-(4-fluorophenylazo)phenol, F(C6H4)N=N(C6H4)OH (1) (C6H4=p-phenylene), 4-(trifluoromethylphenylazo)phenol, CF3(C6H4)N=N(C6H4)OH (2), 4-(4-heptafluoropropylphenylazo)phenol, C3F7(C6H4)N=N(C6H4)OH (3), 4-(4-nonafluorobutylphenylazo)phenol, C4F9(C6H4)N=N(C6H4)OH (4), 4-(4-tridecafluorohexylphenylazo)phenol, C6F13(C6H4)N=N(C6H4)OH (5), and 4-(4-heptadecafluorooctylphenylazo)phenol, C8F17(C6H4)N=N(C6H4)OH (6)) were prepared by the usual diazo coupling reactions using 4-(perfluoroalkyl)aniline and phenol.The monomolecular film formations of the azobenzene derivatives at the air/water interface were investigated by surface pressure measurements to be dependent on the fluoroalkyl chain length (n).The compounds 5 (n=6) and 6 (n=8) formed stable monomolecular films at the air/water interface.
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