Related Experiment Video
Updated: Aug 18, 2025

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Surprising Solid-State ESIPT Emission from Apparently Ordinary Salicyliden Glycinates Schiff Bases
Mateusz M Tomczyk1, Łukasz Przypis1,2, Tomohiro Shiraki3,4
1Faculty of Chemistry, Silesian University of Technology, M. Strzody 9, 44-100 Gliwice, Poland.
Abstract:
Excited-State Intramolecular Photon Transfer (ESIPT) is known for the geometry-related phenolic and imine groups. The Schiff bases formed upon condensation of salicyl aldehyde and glycine led to the formation of ESIPT models. A series of alkali metal salicyliden glycinates were analyzed by X-ray diffraction of their monocrystals and spectroscopy measurements. The X-ray analysis revealed varied hydration levels between the salts. They adapted trans geometry on the imine groups and mostly anticlinal conformation with the neighboring atoms, which is different from the other structurally-related compounds in literature. Fluorescence of these compounds was found for the crystalline forms only. Protonation of the imine nitrogen atom and further proton distribution was consistent with the ESIPT theory, which also explained the observed fluorescence with the highest Stokes shift of 10,181 cm-1 and 10.1% of fluorescence quantum yield for the sodium salt.
Related Concept Videos
Preparation and Reactions of Sulfides
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Amines to Sulfonamides: The Hinsberg Test
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
Acid Halides to Esters: Alcoholysis
Atomic Emission Spectroscopy: Interference
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

