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Xuncheng Liu1, Christopher L Anderson2, Yi Liu

  • 1College of Materials and Metallurgy, Guizhou University, Guiyang 550025, P. R. China.

Accounts of Chemical Research
|June 6, 2023
PubMed
Summary

The p-azaquinodimethane (AQM) motif offers a stable alternative to traditional donor-acceptor designs in organic electronics. AQMs enable the development of novel functional materials with tunable properties for applications in transistors and energy storage.

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Area of Science:

  • Organic electronics
  • Materials science
  • Polymer chemistry

Background:

  • The donor-acceptor design principle has dominated organic electronics for 50 years, leading to material exhaustion.
  • Quinoidal conjugated motifs, while promising, suffer from poor stability, limiting their application.
  • The discovery of the stable p-azaquinodimethane (AQM) motif in 2017 opened new avenues.

Purpose of the Study:

  • To explore the synthesis and applications of novel AQM-based materials.
  • To investigate the electronic and optical properties of AQM derivatives and polymers.
  • To demonstrate the versatility of AQMs in organic electronics, including transistors, energy storage, and photothermal applications.

Main Methods:

  • Synthesis of stable dialkoxy AQM small molecules and polymers.

Related Experiment Videos

  • Incorporation of AQMs into conjugated polymers with aromatic subunits.
  • Development of ionic AQMs (iAQMs) via ditriflate derivatives.
  • Exploration of AQM reactivity for dimerization and light-induced polymerization.
  • Synthesis of pyrazino[2,3-b:5,6-b']diindolizine (PDIz) from AQM ditriflates.

    • Main Results:

    • AQM-based polymers exhibit reduced band gaps and high hole mobilities (>5 cm2 V-1 s-1) in organic field-effect transistors (OFETs).
    • Ionic AQMs (iAQMs) yield conjugated polyelectrolytes (CPEs) with near-infrared I (NIR-I) optical band gaps, showing promise for photothermal therapy.
    • Controllable diradicaloid reactivity of AQMs leads to efficient [2.2]paracyclophane formation and ultrahigh molecular weight polymers for dielectric energy storage.
    • PDIz-based polymers show extremely small band gaps (0.7 eV) extending into the near-infrared II (NIR-II) region with strong photothermal effects.

    Conclusions:

    • AQMs provide a versatile platform for designing functional organic electronic materials, overcoming limitations of traditional approaches.
    • Both stable quinoidal and controllable diradicaloid AQM functionalities contribute to advanced material properties.
    • AQM-based materials demonstrate significant potential for next-generation organic electronics, including high-performance transistors, energy storage, and biomedical applications.