jp060646z_si_001.pdf (89.36 kB)
Structural and Photoluminescence Properties of Excited State Intramolecular Proton Transfer Capable CompoundsPotential Emissive and Electron Transport Materials
journal contribution
posted on 2006-06-29, 00:00 authored by Alexander V. Gaenko, Ajitha Devarajan, Igor V. Tselinskii, Ulf RydeElectronic factors influencing the photoluminescence properties and rates of excited state intramolecular proton
transfer (ESIPT) reaction of o-hydroxy derivatives of 2,5-diphenyl-1,3,4-oxadiazole have been studied. The
potential of these molecules as emissive and electron transport materials in designing improved organic light
emitting diodes (OLEDs) has been studied by analyzing possible reasons for the unusually high Stokes shifts
and ESIPT reaction rates. Time-dependent density functional theory (TDDFT) methods have been used to
calculate the ground and excited state properties of the phototautomers that are the ESIPT reaction products.
We study the relative effect of electron-withdrawing substituents on the proton-acceptor moiety and predict
that the lowest ESIPT rate (1.9 × 1011 s-1) is achieved with a dimethylamino substituent and that the Stokes
shifts are around 11 000 cm-1 for all three derivatives.