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

Abstract

We describe the first example of the synthesis of a tetraoxa[8]circulene with only four substituents by means of BF 3 ·OEt 2 mediated tetramerisation of tert-butyl-1,4-benzoquinone. Two of the four regioisomers of tetra-tert-butyltetraoxa[8]circulene have been isolated and characterised by

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

“…It was found [10] that the tetra-tert-butyltetraoxa [8]circulenes aggregate in solution through a cooperative polymerization mechanism despite an evident functionalisation with bulky tert-butyl substituents. Such fictionalization usually suppress aggregation, which proceeds through a cooperative polymerization mechanism [10].…”

“…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.…”

“…Such fictionalization usually suppress aggregation, which proceeds through a cooperative polymerization mechanism [10]. It is known that substitution with tert-butyl groups gives high solubility for a number of large aromatic molecules in non-polar solvents.…”

“…2), which were previously obtained by mono-tert-butyl-1,4-benzoquinone tetramerization procedure [10].…”

“…Regioisomeric [10] mixture of tetra-tert-butyltetraoxa [8] circulenes (Fig. 2) was purified by standard column chromatography on silica gel using heptane as the mobile phase.…”