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In 2019, chemists reported a molecule that combines radial π-conjugation with a double half-twist: a strained figure-of-eight ribbon made from 12 benzene rings and held around a central 9,9′-bicarbazole. Its π-electron system runs within the overall plane of the ring structure, unlike the familiar arrangement in planar aromatic systems. The enantiomers were stable at room temperature, but the report says they decomposed at elevated temperatures.
What makes this aromatic system radial?
In a common planar aromatic system, the π-orbitals lie parallel to the plane of the ring. In radial conjugation, the π-electron system instead lies within the overall plane of the ring structure, oriented like spokes in a wheel. The 2019 report describes this molecule as the first radially conjugated aromatic system with a double half-twist.
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The description is about the orientation of the π-system, not simply the molecule’s outline. Its architecture is a ribbon of 12 benzene rings, and the rings’ arrangement gives the molecule its distinctive twisted shape.
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A central 9,9′-bicarbazole locks the benzene-ring ribbon into a strained figure-of-eight shape. This unusual structure also makes the molecule chiral: it exists as two mirror-image forms, or enantiomers.
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How was it made, and how were the enantiomers separated?
The report describes a three-step synthesis starting from bicarbazole and a U-shaped 1,4-cyclohexadiene building block. The researchers separated the two enantiomers using supercritical fluid chromatography. The report does not provide enough detail to specify reaction conditions or yields.
Is the molecule stable?
The reported enantiomers were stable at room temperature and decomposed at elevated temperatures. Separately, calculations suggested that the compound was unlikely to racemise—that is, to convert between its two enantiomeric forms. That resistance is a computational prediction, not the same kind of evidence as the reported stability and decomposition observations.
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What could it be used for?
The report presents the molecule as a candidate of interest for materials chemistry. It does not demonstrate a working material or establish a commercial product, so practical applications should be treated as a possibility for further investigation rather than an achieved result.
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