Synthesis, Structures and Properties of Bis(naphthocyclobuta)pyrenes

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 pi-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.

Automated summary

The study revealed that different regioisomeric polycyclic conjugated scaffolds exhibit varied local aromaticity and photophysical properties. Tuning the pi-stacking can lead to a p-type organic semiconductor suitable for solution-processed thin film transistors.