Single-Crystal-to-Single-Crystal (SCSC) Linear Polymerization of a Desymmetrized Anthraphane.

ABSTRACT

In this work we present one of the rare cases of single-crystal-to-single-crystal (SCSC) linear polymerizations, resulting in a novel ladder-type polymer. The polymerization is based on the photoinduced [4+4]-cycloaddition reactions between trifunctional anthracene-based monomers. The careful design of the monomer anthraphane-tri(OMe), results in perfectly stacked anthracene pairs in the crystal structure, with Schmidt's distances d=3.505-3.666 Šand shift s=1.109 Å, allowing a selective linear polymerization in quantitative yields and in a matter of minutes, without compromising the integrity of the single crystals. The obtained polyanthraphane-tri(OMe), reveals moreover a very interesting and unprecedented case of stereoisomerism, which is characteristic for polyanthraphanes.