Process for the manufacture of polyacetylene films from modified electrically conductive polyacetylene

Abstract

Abstract A process for the production of polyacetylene films from modified, electrically conductive polyacetylene, in which a polyacetylene film (I) is reacted with an organic, inorganic or organometallic compound which is suitable for addition onto C=C double bonds and contains either positively polarised halogen atoms or negatively polarised hydrogen atoms in the molecule or is an olefin which is capable of electrophilic 1,4-dipolar addition reactions, and (II) conventional complexing agents are subsequently added. The compound for the reaction (I) may be: ROX where X = F, Cl, Br or I, and R = H, C1-C6-(perhalo)alkyl, (perhalo)aryl, -SO3<(-)> or -ClO3, ROOX where X = F or Cl, and R = -SF5, -CF3 or -C2F5, RNHF where R = C1-C6-(perhalo)alkyl, -SF5, -C(O)OR<1> (where R<1> = C1-C6-(perhalo)alkyl or (perhalo)aryl, RNF2 where R = H, -NF2, C1-C6-(perhalo)alkyl, (perhalo)cycloalkyl, (perhalo)aryl, -SF5, R<1>-SO2-, R<1>-C(O)- or R<1>OC(O)- [where R<1> = C1-C6-(perhalo)alkyl, (perhalo)cycloalkyl or (perhalo)aryl], R2NF where R = C1-C6-(perhalo)alkyl, (perhalo)cycloalkyl, (perhalo)aryl, R<1>-C(O)- [where R<1> = C1-C6-(perhalo)alkyl, (perhalo)cycloalkyl or (perhalo)aryl], -SF5, or -SO2X [where X = F or Cl], N3F, NO2F, NO3F etc. NCl3, NBr3, NI3.x NH3 [where x = 1-3], R-NHX where X = Cl, Br, or I and R = H, C1-C6-alkyl, cycloalkyl, R<1>SO2-, R<1>C(O)-, R<1>OC(O)- [where R<1> = C1-C6-(perhalo)alkyl, (perhalo)cycloalkyl or (perhalo)aryl] or R<3>R<2>P(O)- [where R<3> and R<2> are identical or different and R<3>=R<2>=C1-C6-alkyl, cycloalkyl, aryl, alkoxy or aryloxy], R-NX2 where X = Cl, Br or I and R is one of the abovementioned groups or -SF5, -SO2F or -SO2Cl, R2NX where X = Cl, Br or I and R is one of the abovementioned groups or -SF5, -SO2F, -SO2Cl, (CH3)3Si- or succinidyl, NOCl, NOBr, NOI, N3Br or N3I, ClF, Cl2, Br2, BrCl, BrCl3, BrF3, ICl3 or F2, N2O4 or N2O5, HMR<1>R<2> where R<1> and R<2> are identical or different and are H, C1-C6-alkyl, cycloalkyl, aryl, alkoxy or aryloxy and M = B, Al, Ga, P, As, Sb or Bi, HP(O)R<1>R<2> where R<1> and R<2> are identical or different and are H, OH, C1-C6-alkyl, cycloalkyl, aryl, alkoxy or aryloxy, Bis(cyclopentadienyl)MRH where R = H, C1-C6-alkyl, Cl or Br, and M = Ti, Zr or Hf, Q<1>Q<2>C=CQ<1>Q<2> where Q<1> and Q<2> are identical or different and are H, F, Cl, -CN, -COOR [where R = H, C1-C6-perhaloalkyl, perhalocycloalkyl or perhaloaryl] or cyclically linked Q<1>-Q<2> = -C(O)-O-C(O)-. The complexing agent employed for the reaction (II) may be: an oxidising Lewis acid, for example AsF5, SbF5, SbCl5, VF5 or XeF6, or a non-oxidising Lewis acid plus an oxidising agent, for example PF5 + NOF, AlCl3 + Cl2 or an oxidising protonic acid, for example HClO4, H2SO4 or HNO3, or a non-oxidising acid which is included by anodic oxidation, for example H3PO4, or CF3SO3H, or a salt which is included by anodic oxidation for example NaPF6 or NaBF4, or a highly electropositive metal, for example Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba or a lanthanide, or a tertiary ammonium ion which is included by cathodic reduction.

Inventors

• 👤 Herbert Dr. Naarmann
• 👤 Volker Dr. Muench
• 👤 Klaus Dr. Penzien
• 👤 Dieter Dr. Naegele

Bibliographic Details