Flat-structured boron-nitrogen-substituted heterocyclic compounds with extended conjugated π-systems such as azaborines are fascinating compounds because of their valuable and interesting optical properties making them suitable to be utilized in many optoelectronic devices. We have designed, synthesized, and investigated a series of novel conjugated thermally stable pyrrolidinone-fused 1,2 azaborines (PFAs) chromophores by incorporating a phenyl ring as a spacer linking the chromophore to different electronic moieties as easily tunable high-luminescent organic materials. The addition of a phenyl spacer between the PFA core and the electronic moieties resulted in a red shifted emission and exhibited larger Stokes shift when compared to the parent PFAs. We also examined the effect of the different electronic groups on the PFAs. The addition of a -CN group to the phenyl spacer to make an A-π-D PFA, resulted in the red-shift of the emission wavelengths in all solvents. However, the incorporation of a -NO2 group instead of a -CN group on the phenyl spacer to create an A-π-D PFA, help generated intramolecular charge transfer (ICT) effect and resulted in red-emissive PFAs with λem from 553 – 631 nm. The -NO2 substituted PFA displayed the largest Stokes with Δλ = 251 nm, or Δν = 10,468 cm-1in acetonitrile.

Structural effects on the photophysical properties of tunable pyrrolidinone-fused 1,2 azaborines chromophores with a phenyl spacer

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