β-cyano-oligo(phenylene vinylene)s (β-c-OPVs) are chromophores that fluoresce brightly in both aggregated states or when molecular vibrations are restricted, yet are non-emissive in solution. Tailorable solubility through tail groups allows this dual emission to be exploited in aqueous systems. A β-c-OPV functionalized with sulfonic acid propyloxy groups (SAB β-c-OPV) was synthesized and found to have maximum water solubility of 0.78 mg/mL, with absorbance centered around 362 nm and molar absorptivity of 30,965 L mol-1 cm-1. Frozen aqueous solutions displayed excimer emission around 545 nm with negligible fluorescence at ambient temperature, confirming transference of on-off fluorescence in β-c-OPVs to aqueous environments. A stimuli responsive system was created by incorporating SAB β-c-OPV into methylcellulose solutions and heating them past the lower critical solution temperature to induce gelation. Excimer emission occurred in the solution and emission from isolated molecules was observed in the gels. The shift of peak emission maxima from 517 nm to 436 nm was clearly visible to the eye.

Stimuli responsive β-cyano-oligo(phenylene vinylene) methylcellulose hydrogels

253rd National Meeting (2017)

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