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Polymacrocycles Derived via Ugi Multi-Component Reactions.

Patrick-Kurt Dannecker1, Ansgar Sehlinger1, Michael A R Meier1

  • 1Karlsruhe Institute of Technology, Straße am Forum 7, 76131, Karlsruhe, Germany.

Macromolecular Rapid Communications
|November 21, 2018
PubMed
Summary
This summary is machine-generated.

Researchers demonstrate polymacrocycle synthesis by combining Ugi-4CR macrocyclization with polymerization. This novel approach creates polymers with potential applications in coordination chemistry, such as sensors and catalysts.

Keywords:
ADMETmulticomponent reactionspolycyclesstep-growth polymerizationsthiol-enes

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • The Ugi-4CR reaction is established for macrocycle synthesis.
  • Ugi-4CR has also been utilized for polymerizations, creating a new trend.
  • Polymacrocycles, combining both concepts, represent an underexplored area.

Purpose of the Study:

  • To demonstrate the synthesis of polymacrocycles.
  • To develop a straightforward, two-step procedure for polymacrocycle design.
  • To simplify the Ugi macrocyclization setup through systematic screening.

Main Methods:

  • Utilized the Ugi-4CR reaction with 10-undecenoic acid, a diamine, a diisocyanide, and an aldehyde to form functionalized macrocycles.
  • Employed acyclic diene metathesis (ADMET) polymerization for macrocycle chain extension.
  • Applied thiol-ene polymerization as an alternative method for polymacrocycle generation.

Main Results:

  • Successfully synthesized diversely substituted macrocycles with terminal double bonds via Ugi-4CR.
  • Generated polymacrocycles through ADMET or thiol-ene polymerization of these macrocycles.
  • Simplified the Ugi macrocyclization protocol via systematic reaction screening.

Conclusions:

  • The study presents a novel and efficient method for polymacrocycle synthesis.
  • The resulting polymacrocycles possess potential applications in coordination chemistry, including sensors, filters, and phase-transfer catalysts.
  • The findings open new avenues in polymer chemistry and materials design.