Synthesis, Structures and Properties of Bis(naphthocyclobuta)pyrenes

Abstract This study explored new polycyclic conjugated scaffolds combining pyrene and cyclobutadienoid rings. Regioisomeric bis(naphthocyclobuta)pyrenes were synthesized and characterized by single‐crystal X‐ray crystallography. It was found that the regioisomeric polycyclic conjugated scaffolds exhibit different local aromaticity and photophysical properties as a result of the different fusion patterns of pyrene and cyclobutadienoid. Tuning the π‐stacking of bisnaphtho[2′,3′:3,4]cyclobuta[1,2‐ e :1′,2′‐ l ]pyrene by changing the length of the alkyl substituents led to a p‐type organic semiconductor for solution‐processed thin film transistors.