Cyclo-oligomerization of Quinones. IV. The Action of Strong Acids on 2,3-Dialkyl-p-benzoquinones.

DFT and QTAIM study of the tetra-tert-butyltetraoxa[8]circulene regioisomers structure

“…The symmetric tetraoxa [8]circulenes [1][2][3][4][5][6][7] attract the research interest as a promising electroluminescent material for organic light-emitting diodes (OLEDs) [8][9][10][11]. The first reliable structure description of the simplest symmetric tetraoxa [8]circulene (Fig.…”

Tetra‐tert‐butyltetraoxa[8]circulene and Its Unusual Aggregation Behaviour

“…[10,[12][13] Octaalkyl-substituted tetraoxa [8]circulenes can be prepared from 2,3-dialkyl-1,4-benzoquinones or 1,4-naphthoquinones upon treatment with strong mineral or Lewis acids. [10][11] Here, we show for the first time that a mono-substituted 1,4-benzoquinone may be tetramerised to give a tetraoxa [8]circulene in good yield. This was achieved by treating tert-butyl-1,4-benzoquinone with BF 3 ·OEt 2 in boiling dichloromethane (CH 2 Cl 2 ) to yield tetra-tert-butyltetraoxa [8]circulene (1) in multigram quantities as a mixture of regioisomers with respect to the tert-butyl groups (Scheme 2).…”

Substituted Tetraoxa[8]circulenes - New Members of the Liquid Crystal Family

“…[12,13] Their isolation was facilitated by an extremely low solubility. It was thus an open the compounds shows LC behavior, and the tetraoxa [8]circulenes are thus new candidates for discotic mesogens.…”

“…[11] However, the corresponding oxygen analogue has been known for a number of years, [12] although an investigation of the properties of the tetraoxa [8]circulenes has so far been hampered by the extremely low solubility of the few derivatives known. [13] Figure 1. [8]Circulene and Tetraoxa [8]circulene…”