Ylidenemalononitrile enamine-coated media as fluorescent "turn-on" probes for volatile primary amines.

Two ylidenemalononitrile enamines, adsorbed to various media, undergo a cyclization reaction with primary amine vapors resulting in a fluorometric and colorimetric response. After determining the media with the fastest response rate for emission "turn-on" to be aluminum oxide activated neutral (AON), we further demonstrate the sensitivity (propylamine concentrations as low as 200 ppm are detected) and selectivity to various analytes including amines, methanol, and ethanethiol. Lastly, as an alternative means of detection, the colorimetric response dye on glass filter paper was shown to detect propylamine concentrations as low as 29 ppm.

Ylidenemalononitrile enamines as fluorescent "turn-on" indicators for primary amines.

Ylidenemalononitrile enamines undergo rapid amine exchange followed by a cyclization with primary amines to yield fluorescent products with emission intensities as high as 900 times greater than the starting materials. After identifying the fluorescent species by X-ray crystallography, we demonstrate that the rate of amine exchange is substrate dependent and that by simple structural variation the fluorescence can be tuned over the entire visible spectrum. We further demonstrate their potential application in biomolecule labeling.