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

Acta Crystallogr B Struct Sci Cryst Eng Mater. 2016 Oct 1;72(Pt 5):684-692. doi: 10.1107/S2052520616009343. Epub 2016 Sep 16.

Abstract

The synthesis, characterization, structural analysis and fluorescence properties of two rhodamine 6G derivatives are described, namely a propargylamine derivative, 3',6'-bis(ethylamino)-2',7'-dimethyl-2-(methylcyanide)spiro[isoindole-1,9'-xanthen]-3(2H)-one (I), and a γ-aminobutyric acid (GABA) derivative, 3',6'-bis(ethylamino)-2',7'-dimethyl-3-oxospiro[isoindole-1,9'-xanthen]-2(3H)-yl)butyricacid (II). Both structures are compared with four similar ones from the Cambridge Structural Database (CSD), and the interactions involved in the stabilization are analyzed using the atoms in molecules (AIM) theory. Finally, a single-crystal in-situ reaction study is presented, carried out by fluorescence methods, which enabled the `opening' of the spirolactam ring in the solid phase.

Keywords: atoms in molecules theory; fluorescence; photocrystallography; rhodamine 6G derivatives; weak interactions.

MeSH terms

  • Chemistry Techniques, Synthetic
  • Crystallography, X-Ray
  • Fluorescence
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Models, Molecular*
  • Molecular Structure
  • Rhodamines / chemistry*

Substances

  • Fluorescent Dyes
  • Rhodamines
  • rhodamine 6G