Benzophenanthrothiophenes: Syntheses, Crystal Structures, and Properties

A new class of polycyclic heteroarenes based on benzo­[3,4]­phenanthro­[1,2-b]­benzo­[3,4]­phenanthro­[2,1-d]­thiophene (BPBPT) was prepared from polyaryl thiophenes via regioselective Scholl reactions. The molecular frameworks of these compounds exhibited twisted bridges and near-cofacial packing motifs with oppositely or parallel π-stacked structures depending on the substituents on the periphery. Theoretical calculation of electronic coupling and charge mobility was carried out on the basis of the single-crystal structures. Single crystals of selected benzophenanthrothiophenes were used in p-channel field-effect transistor device fabrication, from which the highest mobility was measured as 2.03 cm2 V–1 s–1 from Flu-BPBPT.