Work

Synthesis of N-doped chiral macrocycles by regioselective palladium-catalyzed arylation

Year: 2025

Type: article

Abstract: A series of nitrogen (N)-doped macrocycles was successfully synthesized through palladium-catalyzed arylation. X-ray crystallographic characterization revealed the formation of isomeric products depending on the substituents on the N atoms. Notably, two intrinsically chiral macrocycles MC1 and MC3 with C 1 symmetry were successfully obtained. These macrocycles exhibit exceptional photophysical properties, particularly remarkable high fluorescence quantum yields (Φ F up to 0.69). Furthermore, enantiomeric resolution of inherent chiral MC1 was achieved using preparative chiral HPLC, enabling detailed investigation of its chiroptical behavior through circular dichroism and circularly polarized luminescence spectroscopy.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.21.149

Authors: Shuhai Qiu, Junzhi Liu

Institutions: University of Hong Kong, State Key Laboratory of Synthetic Chemistry

Language: English

Topic: Supramolecular Chemistry and Complexes

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Natural Science Foundation of China, Chinese Academy of Sciences, University of Hong Kong, Tsinghua University

Awards: G164030836, G2115009338, G4526233296, G8626952308