FLUORESCENCE QUANTUM YIELD OF PERYLENEDIIMIDE
COMPOUNDS
Austėja Bukauskytė1,2, Alytis Gruodis1, Renata Karpič2
1
2
Faculty of Physics, Vilnius University, Saulėtekio Ave. 9-III, LT-10222 Vilnius, Lithuania
Center for Physical Sciences and Technology, Saulėtekio Ave. 3, LT-10257 Vilnius, Lithuania
[email protected]
Perylenediimides (PDIs) are organic materials of high photo and thermal stability, high fluorescence quantum
yields (QY) and chemical inertness. First PDIs had very low solubility so they were used as high quality industrial
pigments, especially for automobiles [1]. New potential applications for PDIs arose when solubility increasing
substituents were introduced (Figure 1 positions R, 1-8).
Due to high fluorescence QY, high thermal and photo stability, PDI compounds are used in luminescence solar
concentrators. Wide absorption in visible region allows application of these compounds in dye sensitized solar cells.
Also, PDI compound possess n-type conductivity, so they can be used in organic solar cells, organic field effect
transistors and organic light emitting diodes. Broad fluorescence spectrum and high photo stability make PDIs excellent
material for developing organic solid-stat lasers [2].
Most of PDIs properties can be modified by introducing different substituents at different positions (Figure 1).
Although, while some substituents can alter PDI’s properties in desired way (for example, increase solubility, widen
absorption or emission spectra), they can also do some negative influence on some properties (for example, substituents
at 1-8 positions can decrease fluorescence QY).
1
2
3
4
O
O
N R
R N
O
O
5
6
7
8
Fig. 1. Molecular structure of PDI molecule with possible substituents positions (R, 1-8)
In this research, properties of newly synthesized PDIs were investigated. These compounds were synthesized by
Dr. Linas Labanauskas group from Center for Physical Sciences and Technology. Dependence of absorbance and
fluorescence spectra on different substituents was discussed. Furthermore, fluorescence QY of all PDIs were
determined employing the comparative method and using two different standards – Fluorescein and Rhodamine 101 [3].
Strong dependence of QY on different substituents was shown. Different substituents have different effects on charge
distribution in excited state. This was also confirmed by quantum chemical calculations. Finally, radiative and nonradiative fluorescence lifetimes of all PDIs were determined and presented.
[1] W. Herbst, K. Hunger, Industrial Organic Pigments Production, Properties, Applications, 3rd ed. WILEY-VCH Verlag GmbH & Co. KGaA,
Weinheim, (2004).
[2] E. M. Calzado, J. M. Villalvilla, P. G. Boj, J. A. Quintana, R. Go´mez, J. L. Segura, M. A. Dı´az-Garcı´a, Effect of Structural Modifications in the
Spectral and Laser Properties of Perylenediimide Derivatives, J. Phys. Chem. C, 111, 13595-13605 (2007).
[3] H. Langhals, J. Karolin, L. B-A. Johansson, Spectroscopic properties of new and convenient standards for measuring fluorescence quantum yields,
J. Chem. Soc., Faraday Trans., 94, 2919-2922, (1998)