Theoretical Study of 1,8-Diaminonaphthalene Polymerization

The polymerization of 1,8-diaminonaphthalene (1,8-DAN) was studied by a theoretical approach based on Hartree-Fock calculations. Investigation of relative stability of most possible dimers, trimers and tetramers yields very useful data concerning the regioselectivity of the coupling reaction as well as the final structures of the polymeric chains. The mechanism is more likely to occur via a radical-radical pathway and leads to mixture of compounds through ortho-C-C and para-C-N linkages.