Solid-state fluorescent 3,3-diarylallylidene indolinones by pseudo-five-component synthesis

One-pot syntheses of 3,3-diarylallylidene indolinones are achieved by pseudo -four-and pseudo-five-component reactions. The title compounds are obtained as a mixture of E/Z-configured isomers. The photophysical char-acteristics are assessed by absorption and solid-state emission spectroscopy. Irrespective of their configuration, the 3,3-diarylallylidene indolinones fluoresce in the solid state for electron-withdrawing and weakly electron -releasing remote p-phenyl substituted dyes with concomitantly Boc substitution of the lactam moiety. DFT and TD DFT calculation reproduce and rationalize the electronic structure of the longest wavelength absorption and emission bands.

Automated summary

One-pot syntheses of 3,3-diarylallylidene indolinones were achieved by pseudo-four-and pseudo-five-component reactions. The title compounds, which are a mixture of E/Z-configured isomers, were assessed for their photophysical characteristics using absorption and solid-state emission spectroscopy. The fluorescence of 3,3-diarylallylidene indolinones in the solid state was observed regardless of their configuration, but only when electron-withdrawing and weakly electron-releasing remote p-phenyl substituted dyes were present with concomitant Boc substitution of the lactam moiety. DFT and TD-DFT calculations were used to reproduce and rationalize the electronic structure of the longest wavelength absorption and emission bands.