Abstract
AbstractIsomeric ortho, meta and para naphthalimide–urea derivatives ND‐2U, ND‐3U and ND‐4U were synthesized and characterized. Upon gentle mechanical stimulation, the weakly emissive ortho isomeric sample ND‐2U was transformed into a yellow‐green emissive material (λem=500 nm), with Δλ≈125 nm. The mechanoluminescent emission of this isomer could be “switched off” by exposing the sample to solvent vapour. Moreover, ND‐2U could respond to fluoride anions in solution with a dramatic enhancement of fluorescence at λ=446 nm. The sigmoidal nature of the binding isotherm suggested cooperative binding of fluoride to the ortho isomer. 1H NMR spectroscopic studies provided vital insights into the nature of ND‐2U/F−complexation, highlighting the role of the proximal 1,8‐naphthalimide motif.
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