Azaacenes Bearing Five-Membered Rings.

Michael GanschowSilke KoserManuel HodeckerFrank RomingerJan FreudenbergAndreas DreuwUwe H F Bunz

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2018)

We report the synthesis of processible (dihydro)pyracyclene- and acenaphthylene-substituted azaacenes using condensation reactions in solution. The targets are characterized via cyclic voltammetry, X-ray crystallography, UV/Vis, fluorescence spectroscopy and DFT/NICS calculations. Formal hydrogenation of the annulated five-membered ring surprisingly alters emission in the solid-state as a consequence of modulation of aromaticity and HOMO-LUMO overlap. Five highly fluorescent, crystalline azaacenes were investigated as emitters in organic light-emitting diodes, and their performance with respect to luminance and efficiency was compared to that of structurally related azaacenes.

Keyphrases

solid state
density functional theory
molecular docking
high resolution
single molecule
molecular dynamics
molecular dynamics simulations
quantum dots
living cells
magnetic resonance imaging
energy transfer
dual energy
fluorescent probe
crystal structure
label free