Dinaphthobenzo[1,2:4,5]dicyclobutadiene with Strong Antiaromaticity and Orthogonally Tunable Electronics and Packing

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.

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