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Facile Synthesis of Diversified Biisoquinoline-Containing Polymers by Multicomponent C─H Activation/Annulation

Jiajun Liao1, Dongyang Fan1, Chao Yang1

  • 1Center for AIE Research, Guangdong Provincial Key Laboratory of New Energy Materials Service Safety, College of Materials Science and Engineering, Shenzhen University, Shenzhen, Guangdong, 518060, China.

Angewandte Chemie (International Ed. in English)
|August 12, 2025
PubMed
Summary

This study introduces a novel one-pot polymerization method for creating diverse biisoquinoline-containing polymers (BCPs). These advanced materials exhibit tunable luminescence and can be used to generate high-resolution fluorescent patterns.

Keywords:
Aggregation‐induced emissionBiisoquinoline‐containing polymerChiral polymerC─H activation/annulationNew polymerization reaction

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Biisoquinoline scaffolds are recognized for their unique photophysical properties and axial chirality, making them valuable in various scientific fields.
  • The synthesis of functional biisoquinoline-containing polymers (BCPs) has been significantly hindered by synthetic complexities, limiting their widespread application.
  • The development of optically active BCPs through asymmetric catalytic polymerization remains an unachieved goal.

Purpose of the Study:

  • To develop an efficient and versatile strategy for synthesizing structurally diverse biisoquinoline-containing polymers (BCPs).
  • To achieve the construction of optically active BCPs via asymmetric catalytic polymerization.
  • To explore the properties and applications of the synthesized BCPs, including their luminescent characteristics and potential in photopatterning.

Main Methods:

  • A multicomponent cascade C─H activation/annulation polymerization (CAAP) strategy was employed.
  • Readily available benzil derivatives, internal diynes, and ammonium acetate were used as starting materials.
  • Rhodium catalysts were utilized for both achiral and asymmetric CAAP reactions, conducted in a one-pot, one-step operation under air.

Main Results:

  • A variety of multisubstituted BCPs with high molecular weights (up to 49900 g mol⁻¹) were synthesized in good yields.
  • The resulting BCPs demonstrated excellent solubility, good film-forming capabilities, and tunable luminescent properties.
  • Optically active BCPs and BCP-metal complexes with stable axially chiral configurations were successfully generated using chiral rhodium catalysts.

Conclusions:

  • The developed CAAP strategy provides facile access to diverse BCPs, overcoming previous synthetic limitations.
  • The synthesized BCPs possess desirable properties for applications in materials science, particularly in creating high-resolution fluorescent photopatterns.
  • This work represents the first successful construction of optically active BCPs via asymmetric catalytic polymerization, opening new avenues for chiral materials development.