Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 35314682.
- Also identified by DOI 10.1038/s41467-022-29106-w and PMC identifier 8938435.
- No licence information is recorded for this record.
- Because redistribution is not established, this page shows the abstract only. Follow the links below for the full text.
Abstract
A fully conjugated azacorannulene dimer with a large π-surface (76π system) was successfully synthesized from a fully conjugated bifunctional polycyclic aromatic azomethine ylide. This molecule represents an example of diaza[80]fullerene (C<sub>78</sub>N<sub>2</sub>) fragment molecule bearing two internal nitrogen atoms. X-ray crystallography analysis shows its boat-shaped structure with two terminal azacorannulenes bent in the same direction. The molecular shape leads to unique selective association with a dumbbell-shaped C<sub>60</sub> dimer (C<sub>120</sub>) over C<sub>60</sub> through shape recognition. Owing to its large π-surface and a narrow HOMO-LUMO gap, the azacorannulene dimer exhibits red fluorescence with a quantum yield of up to 31%. The utilization of the fully conjugated bifunctional azomethine ylide is a powerful method for the bottom-up synthesis of large multiazafullerene fragments, providing a step towards the selective total synthesis of multiazafullerenes.