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Picosecond Switchable Azo Dyes.

Jaume Garcia-Amorós1, Benjamin Maerz2, Marta Reig1

  • 1Grup de Materials Orgànics, Institut de Nanociència i Nanotecnologia (IN2UB), Departament de Química Inorgànica i Orgànica, (Secció de Química Orgànica), Universitat de Barcelona, Martí i Franquès 1, 08028, Barcelona, Spain.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 30, 2019
PubMed
Summary

New azo dyes with thiazole/benzothiazole and amino groups switch isomers in subnanoseconds. These light-sensitive molecules demonstrate rapid thermal back reactions, enabling fast, reversible switching under ambient conditions.

Keywords:
ab initio calculationsazo compoundsisomerizationmolecular switchesultrafast spectroscopy

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Materials Science

Background:

  • Azo dyes are known for their light-sensitive properties.
  • Controlling the kinetics of isomerization in molecular systems is crucial for developing advanced materials.
  • Subnanosecond switching speeds are highly desirable for applications in molecular electronics and photonics.

Purpose of the Study:

  • To synthesize and characterize novel azo dyes incorporating electron-withdrawing thiazole/benzothiazole heterocycles and electron-donating amino groups.
  • To investigate the thermal isomerization kinetics of these azo dyes and their corresponding salts.
  • To explore the potential of these molecular platforms for ultrafast, reversible photo-switching applications.

Main Methods:

  • Synthesis of novel azo dye molecules and their corresponding salts.
  • Kinetic studies using time-resolved spectroscopy to determine relaxation times.
  • Theoretical calculations (e.g., DFT) to determine activation energies for isomerization.

Main Results:

  • Azo dyes with thiazole/benzothiazole and amino groups exhibited thermal isomerization kinetics in the milli- and microsecond timescales.
  • The corresponding benzothiazolium and thiazolium salts showed significantly faster thermal back reactions in the picosecond domain.
  • These molecular azo derivatives achieved reversible trans-cis isomerization switching within a subnanosecond timescale under ambient conditions.
  • Theoretical calculations confirmed very low activation energies, consistent with the observed ultrafast kinetics.

Conclusions:

  • Novel azo dye structures enable unprecedented subnanosecond reversible photo-switching at room temperature.
  • The incorporation of specific heterocyclic and amino groups significantly accelerates isomerization kinetics.
  • These findings pave the way for the development of advanced molecular switches and light-responsive materials operating at ultrafast timescales.