Dinaphthobenzo[1,2:4,5]dicyclobutadiene with Strong Antiaromaticity and Orthogonally Tunable Electronics and Packing.
Angewandte Chemie (International ed. in English)
Polycyclic conjugated hydrocarbons containing antiaromatic four-membered cyclobutadienoids are of great fundamental and technical interest. However, their challenging synthesis has hampered the exploration and understanding of such systems. We report herein a modular and efficient synthesis of novel CBD-containing acene analogues, dinaphthobenzo[1,2:4,5]dicyclobutadiene (DNBDCs) with orthogonally tunable electronic properties and molecular packing. Our design also features strong antiaromaticity of CBD units, as revealed by nucleus-independent chemical shift and anisotropy of the induced current density calculations as well as X-ray crystallography. Tuning the size of silyl substituents resulted in the most favorable "brick-layer" packing for triisobutylsilyl-DNBDC and a charge mobility of up to 0.52 cm2 V-1 s-1 in field-effect transistors.
View details for PubMedID 30565363