π-Conjugation extension in N-aryl isoindolinones enables rational control of excited-state pathways and fluorescence efficiency. Stepwise π-extension enhances fluorescence quantum yield from 0.04 to 0.58 while maintaining large Stokes shifts. Photophysical measurements and theoretical calculations suggest that the enhanced fluorescence efficiency is associated with modulation of excited-state pathways, including reduced ISC probability and TICT-like structural relaxation. These findings indicate that the isoindolinone framework provides a versatile platform for designing highly emissive chromophores through precise control of excited-state dynamics.
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