Indacenodipyrene containing small molecules and ladder polymers

A series of s-indaceno[1,2,3-cd:5,6,7-c'd']dipyrene-containing small molecules 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 1.68–2.03 ​eV. Organic field effect transistors were prepared with derivatives giving hole mobilities up to 2.5 X 10⁻⁵ cm²V⁻¹s⁻¹.