Volume 8 • Issue 4 • 1000355
J Chem Eng Process Technol, an open access journal
ISSN: 2157-7048
Research Article
Idzik et al., J Chem Eng Process Technol 2017, 8:4
DOI: 10.4172/2157-7048.1000355
Research Article Open Access
Journal of
Chemical Engineering & Process Technology
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ISSN: 2157-7048
*Corresponding authors: Krzysztof R Idzik, Department of Applied Geology,
Georg-August University of Göttingen, Goldschmidtstr, Göttingen, Germany, Tel:
+495513912861; E-mail: krzysztof.idzik@pwr.wroc.pl
Simone Techert, Deutsches Elektronen-Synchrotron (DESY), Notkestrasse 85,
22607 Hamburg, Germany, Tel: +495512011268; E-mail: stecher@gwdg.de
Received September 27, 2017; Accepted October 07, 2017; Published October 15,
2017
Citation: Idzik KR, Cywiński PJ, Kuznik W, Glaser L, Techert S (2017) Optical
Properties and Quantum-Chemical Calculations of Various Bithienyl Derivatives of
Benzene, Triazine and Triphenyltriazine as Organic Light Emitting Diodes. J Chem
Eng Process Technol 8: 355. doi: 10.4172/2157-7048.1000355
Copyright: © 2017 Idzik KR et al. This is an open-access article distributed under
the terms of the Creative Commons Attribution License, which permits unrestricted
use, distribution, and reproduction in any medium, provided the original author and
source are credited.
Optical Properties and Quantum-Chemical Calculations of Various
Bithienyl Derivatives of Benzene, Triazine and Triphenyltriazine as
Organic Light Emitting Diodes
Krzysztof R Idzik
1,2,3
*, Piotr J Cywiński
4
, Wojciech Kuznik
5
, Leif Glaser
2
and Simone Techert
2,3,6
1
Department of Applied Geology, Georg-August University of Göttingen, Goldschmidtstr. 1, 37077 Göttingen, Germany
2
Deutsches Elektronen-Synchrotron (DESY), Notkestrasse 85, 22607 Hamburg, Germany
3
Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany
4
Functional Materials and Devices, Fraunhofer Institute for Applied Polymer Research, Geiselbergstr. 69, 14476 Potsdam-Golm, Germany
5
Department of Electrical Engineering, Czestochowa University of Technology, Armii Krajowej 1742-201 Czestochowa, Poland
6
Institute of X-Ray Physics, Georg-August Universität, Göttingen, Friedrich-Hund-Platz 1, 37077 Göttingen, Germany
Abstract
Derivatives of tris (2,2-bithiophen-5-yl) derivatives based on a benzene, a triazine or a triphenyltriazine core are
presented for optical light emitting diode functionality. Optical properties as well as their corresponding molecular
energy levels were investigated by UV-VIS absorption supported by fuorescence spectra. Furthermore, DFT and
TDDFT calculations for obtained materials are presented to supplement the experimental data. It is demonstrated
that HOMO - LUMO orbitals are delocalized uniformly on aromatic core and bithienyl substituents. Additionally, an
OLED was built using synthesized compounds to facilitate electron transport and act as light emitting layer. Optical
and charge transport properties along with good electrochemical stability confrm potential application of bithiophene-
aromatic hybrids in electrochromic devices, light emitting electrochemical cells and spintronics.
Keywords: Bithiophene; Fluorescence spectroscopy; DFT
calculations; TDDFT simulations; OLED
Introduction
Symmetrical starting materials are useful building blocks for
designing complex target molecules. Te structural symmetry can be
used to reduce the number of steps necessary for the synthesis of a target
molecule. Symmetrical molecules are also ofen used as central cores in
various oligomers [1].
Organic π-conjugated structures containing thiophene units play
an important role in the search for new materials and their novel
applications such as organic solar cells [2,3] or organic feld efect
transistors [4]. In this case, the interest in thiophenes is associated with
high hole mobility. Tiophenes with well-defned chemical structures
have recently attracted great attention not only as an example of
model compounds for conducting materials, but also as a new class of
functional π-electron systems [5-11]. Branched oligothiophenes based
on central phenyl core have come to the fore over the last several years,
acting both as monomers in cross-linked semiconducting polymers
[12-15] and as components of conjugated dendrimers [16-18].
Some of the 2,4,6-trisubstituted-1,3,5-triazine derivatives exhibit
properties characteristic for liquid crystalline materials and fnd
applications in coordination chemistry and crystal engineering [19-22].
On the other hand, star-shaped systems possessing donor–acceptor
intramolecular arrangement can exhibit strong internal charge transfer
band at low energy levels and therefore, have found applications in
organic solar cells [23].
Over the last decade, highly efcient blue OLEDs have attracted
considerable attention due to their potential applications in full color
ultra-thin fat panel displays [24-30]. Organic light sources are currently
made from either low molecular weight organic materials or polymers.
For the former, the layer structure of the OLED is usually deposited on
a rigid base made from glass or metal [31-34].
In the current work a series of planar donor–acceptor systems based
on an electron-withdrawing triazine core substituted at the 2,4 and 6
positions with various electron-donating bithiophene branches are
presented. Te optical, structural and functuional properties of these
systems are compared to a series of symmetric molecules based on
benzene and triphenyltriazine core. Tey are connected to bithiophene
units and derivatives containing triazine core. For a systematic
study and rational of OLED functionality UV-Vis, steady-state and
time-resolved fuorescence spectroscopy have been performed. Te
studies are supported DFT calculations and TDDFT simulations.
Finally functionalizing studies of an OLED device using synthesized
low molecular weight material as electron transport with the new
compounds as light emitting layers are summarized.
All compounds studied in this work were obtained by the Stille
cross-coupling methodology according to the procedure reported in
our previous work [35].
Results and Discussion
Optical measurements
Optical studies reveal valence electron transition in the visible
and UV regime. All reported bithiophene derivatives were studied
using UV-VIS spectroscopy. Electronic absorption spectra collected
for bithiophene derivatives in chloroform are presented in Figure