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New phenothiazine derivatives (NAS-1, NAS-2) show unique light-responsive properties. Bent NAS-2 crystals exhibit mechanochromism and excimer emission due to facilitated pi-pi stacking, unlike planar NAS and NAS-1.

Keywords:
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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Phenothiazine derivatives are crucial in various applications.
  • Understanding structure-property relationships in organic molecules is vital.
  • Steric strain can significantly influence molecular conformation and photophysical behavior.

Purpose of the Study:

  • To design and synthesize novel phenothiazine derivatives, NAS-1 and NAS-2, as constitutional isomers.
  • To investigate the impact of steric strain on molecular structure and photophysical properties in solution and solid states.
  • To explore the phenomenon of photoinduced structural planarization (PISP) and emission mechanochromism.

Main Methods:

  • Synthesis of 7-phenyl-7H-benzo[c]phenothiazine (NAS-1) and 12-phenyl-12H-benzo[a]phenothiazine (NAS-2).
  • Spectroscopic analysis (UV-Vis absorption, fluorescence emission) in solution.
  • Crystallography to determine solid-state structures.
  • Photophysical measurements, including photoinduced structural planarization (PISP) studies.
  • Emission mechanochromism experiments and two-photon-coupled depth-dependent emission analysis.

Main Results:

  • NAS-1 and NAS-2 were successfully synthesized as constitutional isomers with differing steric strains.
  • In solution, the strained NAS-2 exhibited a bent structure and underwent photoinduced structural planarization (PISP).
  • In the crystal state, bent NAS-2 displayed prominent excimer emission and emission mechanochromism, unlike planar NAS and NAS-1.
  • The bent core of NAS-2 facilitates pi-pi stacking of naphthalene moieties, leading to mechanochromism.
  • Depth-dependent emission revealed spectral differences between the surface and kernel of NAS-2 crystals.

Conclusions:

  • Constitutional isomerism in phenothiazine derivatives leads to distinct structural and photophysical properties.
  • Bent molecular structures can promote intermolecular interactions like pi-pi stacking in the solid state, enabling phenomena like emission mechanochromism.
  • NAS-2 represents a novel material exhibiting both photoinduced structural planarization and emission mechanochromism.
  • The observed depth-dependent emission in NAS-2 crystals suggests a generalizable approach for studying mechanochromic materials.