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An easily accessible isospiropyran switch.

Taylor A Neal1, Jennifer F Neal, Allyson B Eippert

  • 1Department of Chemistry & Biochemistry, The Ohio State University, 100 West 18th Avenue, 43210 Columbus, Ohio, USA. badjic.1@osu.edu.

Organic & Biomolecular Chemistry
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Summary
This summary is machine-generated.

A novel isospiropyran switch was synthesized and demonstrated reversible color changes with acid-base stimuli. This switchable compound shows potential for dynamic materials and chemosensors.

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Area of Science:

  • Organic Chemistry
  • Materials Science

Background:

  • Isospiropyrans are known for their photochromic and thermochromic properties.
  • Developing novel switchable compounds with tunable properties is crucial for advanced applications.

Purpose of the Study:

  • To synthesize a novel isospiropyran switch.
  • To investigate its acid-base responsive chromic behavior.
  • To explore its potential applications in dynamic materials and sensing.

Main Methods:

  • Tandem aldol condensation reaction in the presence of SiCl4.
  • X-ray crystallography for structural confirmation.
  • UV-Vis spectroscopy to monitor acid-base induced color changes.
  • Printing on silica plates to observe solid-state behavior.

Main Results:

  • A novel isospiropyran switch was synthesized in 69% yield.
  • The compound exhibited reversible color changes from colorless to red upon protonation with CH3SO3H and deprotonation with Et3N, repeatable over six cycles.
  • When printed on silica, it formed a blue color attributed to hydrogen bonding, which could be temporarily erased and restored.

Conclusions:

  • The synthesized isospiropyran is an easily accessible, chromic, modular, and switchable compound.
  • It demonstrates significant potential for incorporation into dynamic materials, chemosensors, molecular machines, and organic electronic devices.