The geometric and chemically related structural motifs of tribenzotriquinacene (TBTQ, 1) and triptycene (2) have been merged for the first time on the level of the parent hydrocarbons. A classical cyclodehydration strategy was used to synthesize 1,4-dimethoxytribenzotriquinacene 13 and convert it into the corresponding TBTQ-based para-benzoquinone 4. The Diels–Alder reaction of 4 with anthracene afforded anti- and syn-cycloadducts 22 and 23, respectively, in the ratio of 1:3, which were transformed into dibenzo(triptyceno)triquinacene 5, a new parent polycyclic aromatic hydrocarbon, and derivatives 25–28. The structure of TBTQ-quinone 4 was also extended to give related 1,4-anthraquinone 32. The intriguing geometrical and structural aspects of the merged TBTQ-triptycene motif were examined by X-ray crystal analysis and molecular modeling with the aim to construct tris(triptyceno)triquinacenes, hypothetical analogues that are characterized by a deep molecular cavity.
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|Titolo:||Merging Tribenzotriquinacene and Triptycene|
|Data di pubblicazione:||2016|
|Appare nelle tipologie:||01.01 - Articolo su rivista|