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Dinaphthobenzo[1,2:4,5]dicyclobutadiene: Antiaromatic and Orthogonally Tunable Electronics and Packing
Ist Teil von
Angewandte Chemie (International ed.), 2019-02, Vol.58 (7), p.2034-2039
Auflage
International ed. in English
Ort / Verlag
Germany: Wiley Subscription Services, Inc
Erscheinungsjahr
2019
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
Polycyclic conjugated hydrocarbons containing antiaromatic four‐membered cyclobutadienoids (CDB) are of great fundamental and technical interest. However, their challenging synthesis has hampered the exploration and understanding of such systems. Reported herein is 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. The design also features strong antiaromaticity of the 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.
Introducing strong antiaromaticity: Reported here is a modular and efficient synthesis of a series of dinaphthobenzo[1,2:4,5]dicyclobutadienes with strong antiaromaticity, orthogonally tunable electronics and molecular packing, and high charge mobility. These features allow the application of the structures in organic electronics. CANAL=catalytic arene‐(oxa)norbornene annulation.