Indacenodipyrene Containing Small Molecules and Ladder Polymers

A series of s-indaceno[1,2,3-cd:5,6,7-c'd']dipyrene-containing small molecule and ladder polymers were prepared using a palladium catalyzed arylation reaction. Precursor polymers and their resulting ladder polymers with molecular weights up to 13 kDa were prepared. The rigid, planar materials possessed highest occupied molecular orbital (HOMO) energies of -5.39 to -5.23 eV, lowest unoccupied molecular orbitals (LUMO) energies of -2.42 eV to -2.98 eV, and optical gaps of 1.68 to 2.03 eV. Organic field effect transistors were prepared with derivatives giving hole mobilities up to 2.5 X 10-5 cm2V-1s-1.