Designing new molecules that emit light is an active area of research given their importance in molecular electronics applications, particularly for sensors and OLEDs.  Molecules with emissive properties that are sensitive to multiple external stimuli are particularly attractive targets.  V-shaped molecules with twisted structures that prevent π-π stacking have been reported that exhibit aggregation-induced emission enhancement (AIEE).  We have discovered structurally-related V-shaped molecules containing donor-acceptor (DA) units that impart these molecules with both emission solvatochromism and AIEE behavior.  Therefore, the emissive properties of these new chromophores are addressable as a function of solvent polarity and aggregation state, respectively.  Synthesis was carried out in two steps from commercially available starting materials to produce DA molecules with a quinoxaline acceptor that is <i>ortho</i>-disubstituted with phenyl rings attached to various donors.  The photophysical properties of these molecules were measured in various solvents and found to be emissive and solvatochromic across a wide polarity range.  Additionally, their AIEE behavior manifests in solutions with high water content and in the solid state.  Synthesis, photophysical and AIEE properties, and computational studies of these new V-shaped DA chromophores will be presented.

Solvatochromism and aggregation-induced emission enhancement in V-shaped donor-acceptor molecules

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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