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Two rhodamine 6G derivative compounds: a structural and fluorescence single-crystal study.

Matias Di Paolo1, Mariano L Bossi1, Ricardo Baggio2

  • 1Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pab. II (1428), Buenos Aires, Argentina.

Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials
|October 5, 2016
PubMed
Summary

Two novel rhodamine 6G derivatives, a propargylamine and a gamma-aminobutyric acid (GABA) derivative, were synthesized and characterized. Their solid-state reactivity was studied using fluorescence, revealing spirolactam ring opening.

Keywords:
atoms in molecules theoryfluorescencephotocrystallographyrhodamine 6G derivativesweak interactions

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Crystallography

Background:

  • Rhodamine 6G derivatives are widely used as fluorescent dyes and probes.
  • Understanding the solid-state behavior of such compounds is crucial for developing new materials and applications.
  • Spirolactam structures in rhodamine dyes can undergo ring-opening reactions, influencing their photophysical properties.

Purpose of the Study:

  • To synthesize and characterize two new rhodamine 6G derivatives: a propargylamine derivative (I) and a gamma-aminobutyric acid (GABA) derivative (II).
  • To perform a comparative structural analysis of these derivatives with similar compounds from the Cambridge Structural Database (CSD).
  • To investigate the solid-state reactivity and fluorescence properties of the synthesized compounds, particularly the spirolactam ring opening.

Main Methods:

  • Synthesis of rhodamine 6G derivatives.
  • Characterization using spectroscopic techniques (e.g., NMR, Mass Spectrometry).
  • Single-crystal X-ray diffraction for structural analysis.
  • Atoms in Molecules (AIM) theory for analyzing intermolecular interactions.
  • In-situ fluorescence spectroscopy for studying solid-state reactions.

Main Results:

  • Successful synthesis and full characterization of two novel rhodamine 6G derivatives.
  • Detailed structural comparison with existing CSD entries, highlighting key differences and similarities.
  • AIM analysis revealed significant intermolecular interactions contributing to structural stabilization.
  • In-situ fluorescence studies demonstrated the 'opening' of the spirolactam ring in the solid phase under specific conditions.

Conclusions:

  • The synthesized rhodamine 6G derivatives exhibit unique structural features and intermolecular interactions.
  • The study provides insights into the solid-state reactivity of spirolactam-containing rhodamine dyes.
  • Fluorescence-based in-situ studies are effective for monitoring solid-phase transformations in crystalline materials.