A Biphenyl Containing Two Electron-Donating and Two Electron-Accepting Moieties: A Rigid and Small Donor–Acceptor–Donor Ladder System

Papers published
T. W. Greulich, N. Suzuki, C. G. Daniliuc, A. Fukazawa, E. Yamaguchi, A. Studer, S. Yamaguchi, Chem. Commun., 2015 Advanced Article. DOI: 10.1039/C5CC03063C
  • Incorporation of main group elements into a π-skeleton as a bridging unit is an effective strategy to gain specific properties. Phosphorous atom is particularly useful to tune photophysical properties through simple chemical modifications. Herein, we presented the synthesis of a biphenyl derivative featuring two electron-withdrawing phosphoryl (P=O) bridging units in a ladder fashion together with two electron-donating amino groups at the termini. Thus obtained bis(phenylphosphoryl)-bridged benzidine exhibited an orange fluorescence in a polar solvent. However, despite its donor-acceptor-donor-type structure, this compound did not show any significant solvatochromism on the absorption and emission spectra, whereas maintaining a large Stokes shift. These results represent a unique character of this “smallest ladder” donor-acceptor-donor π-conjugated scaffold.

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