An unprecedented cation radical chain Diels-Alder polymerization leading to novel carbazole polymers

The polymerization of 3,6-bis(trans-1'-propenyl)-N-phenylcarbazole in the p resence of tris(4-bromophenyl aminium hexachloroantimonate (1(+.)) leads to soluble, high molecular weight, thermally stable cycloaddition polymers co ntaining carbazole units in the main polymer chain. The reaction appears to proceed via a highly efficient cation radical chain mechanism which circum vents the usual hole transfer step of the propagation cycle. This polymeriz ation represents the first observation of direct cation radical Diels-Alder cycloaddition polymerization. (C) 2001 Elsevier Science Ltd. All rights re served.