Unprecedented rearrangement of diketopyrrolopyrroles leads to structurally unique chromophores.

Olena Vakuliuk Shota Ooi Irena Deperasińska Olga Staszewska-Krajewska Marzena Banasiewicz Bolesław Kozankiewicz Oksana Danylyuk Daniel T Gryko

Published in: Chemical communications (Cambridge, England) (2018)

Diketopyrrolopyrroles possessing thienyl, furyl and benzofuryl substituents undergo unprecedented skeletal rearrangement in the presence of trimethylsilyl bromide resulting in the formation of thieno[2,3-f]isoindole-5,8-diones and furo[2,3-f]isoindole-5,8-diones. These relatively small dyes possess favorable photophysical properties with the emission maxima within the range of 573-624 nm, large fluorescence quantum yields, moderate sensitivity of emission to solvent polarity and a HOMO-LUMO gap of ca. 1.8 eV.

Keyphrases

energy transfer
molecular dynamics
photodynamic therapy
single molecule
high intensity
solid state
solar cells