A series of four cyano-containing oligo(phenylene vinylene) (cyano-OPV) chromophores was synthesized via Knoevenagel condensation. Functional groups with varying electron donating strength were incorporated to explore their effect on the “push-pull” conjugated system. The optical properties of the chromophores were analyzed via UV-VIS and fluorescence spectroscopy. As the donating groups changed from hydrogen to alkyl to methoxy, both the absorbance and emission maxima were increasingly red-shifted. Binary, on-off fluorescent emission was observed and was related to the rigidity of the chemical environment. Liquid solutions of all chromophores displayed no fluorescence, while frozen samples were highly emissive. Piezochromic stimuli response of a novel chromophore was discovered. Using mechanical grinding, a color change easily discernable to the eye, corresponding to a shift in maximum emission wavelength from 523 to 540 nm was observed. This piezochromic behavior could be controlled at the molecular level via the length of aliphatic tails on the terminal ends of the cyano-OPVs.

Stimuli responsive cyano-oligo(phenylene vinylenes)

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.