Inherently Chiral Calix[4]arenes

Up to 96% ee

Efficient construction of calixarenes with multiple C─C axial stereogenic elements via chiral phosphoric acid-catalyzed lower-rim asymmetric functionalization, providing novel chiral scaffolds for optoelectronic materials.

Chang, Yu · Qin, Wenling · Cera, Gianpiero · Yan, Hailong

Angewandte Chemie - International Edition 2025

Specifications

Enantioselectivity

{'zh': '96', 'en': '96'} %

Advantages

Photocatalytic derivatization

The obtained lower-rim functionalized products can undergo photocatalytic transformations to access novel naphthofuran-based architectures, expanding structural diversity.

Stepwise mechanism elucidated

Mechanistic studies reveal a stepwise process with the stereoselectivity-determining step in the first VQMs-mediated cyclization and a chiral transfer in the second step, providing a basis for rational design.

Applications

• Chiral optoelectronic materials：Provide novel chiral scaffolds with chiroptical response for circularly polarized luminescent materials.
• Chiral light-emitting devices：Induce circularly polarized electroluminescence for improved device performance.
• Chiral macrocyclic supramolecules：Serve as inherently chiral macrocyclic platform for molecular recognition and self-assembly.