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Related Experiment Videos

Fast and stable photochromic oxazines.

Massimiliano Tomasulo1, Salvatore Sortino, Andrew J P White

  • 1Center for Supramolecular Science, Department of Chemistry, University of Miami, 1301 Memorial Drive, Florida, 33146-0431, USA.

The Journal of Organic Chemistry
|November 10, 2005
PubMed
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We developed novel photochromic compounds that switch isomers rapidly using light or heat. These compounds exhibit excellent fatigue resistance, enabling potential applications in responsive materials and molecular devices.

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Photochromic compounds are crucial for developing smart materials.
  • Developing compounds with fast switching speeds and high stability is an ongoing challenge.

Purpose of the Study:

  • To design and synthesize novel photochromic compounds with fused indoline and benzooxazine fragments.
  • To investigate the thermal and photochemical properties of these new compounds.
  • To assess their potential for applications in photoresponsive materials.

Main Methods:

  • Synthesis of novel photochromic compounds.
  • Variable-temperature 1H NMR spectroscopy for thermal analysis.
  • Laser excitation studies to determine photochemical properties.

Related Experiment Videos

  • Chemical trapping to detect transient species.
  • Performance evaluation in poly(methyl methacrylate) matrices.

    • Main Results:

    • Synthesized two photochromic compounds with fused indoline and benzooxazine.
    • Demonstrated thermal ring-opening with barriers of 14–19 kcal mol(-1).
    • Achieved photoinduced ring-opening in <6 ns with quantum yields up to 0.1.
    • Generated a 4-nitrophenolate chromophore absorbing at 440 nm.
    • Observed rapid reversion to the original isomer (22 ns lifetime).
    • Exhibited excellent fatigue resistance over thousands of cycles.
    • Showcased efficient performance in polymer matrices with submillisecond thermal re-isomerization.

    Conclusions:

    • The designed compounds exhibit rapid, light-induced, and thermally reversible photochromism.
    • Their fast switching kinetics and high fatigue resistance are promising for advanced applications.
    • These compounds represent a new class of photochromic materials with significant potential.