Arabian Journal of Chemistry (2013) xxx, xxx–xxx

King Saud University

Arabian Journal of Chemistry

www.ksu.edu.sa
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ORIGINAL ARTICLE

DFT and TD-DFT study on the optical

and electronic properties of derivatives
of 1,4-bis(2-substituted-1,3,4-oxadiazole)benzene
Fuyu Sun a, Ruifa Jin b,*

a
College of Physical and Electronic and Information Engineering, Chifeng University, Chifeng 024000, China
b
College of Chemistry and Chemical Engineering, Chifeng University, Chifeng 024000, China

Received 31 May 2013; accepted 19 November 2013

KEYWORDS Abstract A series of 1,4-bis(2-substituted-1,3,4-oxadiazole)benzene derivatives has been designed

1,4-Bis(2-substituted-1,3,4-
oxadiazole)benzene;
Organic light-emitting diodes
(OLEDs);
Absorption spectra;
Fluorescence spectra;
Reorganization energy
to explore their optical, electronic, and charge transport properties for luminescent and charge
transport materials. The frontier molecular orbitals (FMOs) analysis have turned out that the ver-
tical electronic transitions of absorption and emission are characterized as intramolecular charge
transfer (ICT). Both kabs and kfl of the derivatives with 2-thiophene and 2-1H-pyrrole fragments
show bathochromic shifts compared with parent compound 2-pyridyl substituted derivative (1),
while the corresponding values of the substituted derivatives with 4-pyridyl, 2-pyrazine, and phenyl
fragments are similar to those of parent compound 1. Our results suggest that the substituted deriv-
atives with 4-pyridyl, 2-pyrazine, phenyl, 2-thiophene, and 2-1H-pyrrole fragments are expected to
be promising candidates for luminescent materials for OLEDs. Furthermore, the substituted deriv-
atives with 4-pyridyl, 2-pyrazine, phenyl, and 2-thiophene fragments can be used as promising elec-
tron transport materials, while the substituted derivatives with 2-pyrazine and 2-1H-pyrrole
fragments can be used as promising hole transport materials. In addition, the substituted derivative
with 2-pyrazine fragment may be used as good candidate for ambipolar charge transport material
for OLEDs.
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1. Introduction

The development of organic light-emitting diodes (OLEDs) has

* Corresponding author. Tel./fax: +86 0476 8300370.
E-mail address: Ruifajin@163.com (R. Jin).
Peer review under responsibility of King Saud University.
Production and hosting by Elsevier
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http://dx.doi.org/10.1016/j.arabjc.2013.11.037
attracted great attention during the past decade because of their
potential applications in a new generation of display and light-
ing technologies (Müllen and Scherf, 2006; Walzer et al., 2007;
Grimsdale et al., 2009; Katz et al., 2001). 1,3,4-Oxadiazole
derivatives are highly attractive compounds in the research
and development of materials for OLEDs devices since these
compounds possess high electron-accepting properties and

Please cite this article in press as: Sun, F., Jin, R. DFT and TD-DFT study on the optical and electronic properties of derivatives of 1,4-bis(2-
substituted-1,3,4-oxadiazole)benzene. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.11.037
2 F. Sun, R. Jin
exhibit strong fluorescence with high quantum yields (Ono
et al., 2008; Hughes and Bryce, 2005; Hegelund et al., 2007).
Thus, compounds containing 1,3,4-oxadiazole fragments have
been used as electron-transporting layers, hole-blocking layers,
and light-emission layers in OLEDs devices (Wang et al., 1999;
Antoniadis et al., 1998; Hu et al., 2003). Many strategies have
been used to improve the photoluminescent efficiency of
OLEDs. The optimization method to improve the performance
of OLEDs is that which introduced electron transport moieties
into the main luminophor (Feng et al., 2008; Jin et al., 2003).
Several 1,3,4-oxadiazole derivatives have been actually used
as electron-injection materials to improve the balance of charge
carrier and to increase the photon/electron quantum efficiency
(Zhang et al., 1994). Charge transport is one of the most impor-
tant properties in the performance of OLEDs (Tang and VanS-
lyke, 1987). The location of the electron–hole recombination
zone where excitons are created and light is emitted is directly
affected by the mobilities of electrons and holes in the materials
(Lin et al., 2005). 1,3,4-Oxadiazole derivatives are believed to
be excellent charge transport materials (Wang et al., 1999;
Antoniadis et al., 1998; Hu et al., 2003). Understanding the
relationship between molecular structure and charge transport
property of a material is a key point for providing guideline for
device design, and a great theoretical research effort is currently
being made in this regard (Sitha et al., 2005; Raghunath et al.,
2006).
Two novel compounds of symmetrical bis-1,3,4-oxadiazoles
were prepared by Chen et al. (2007). It was found that these
compounds exhibit strong fluorescence with high quantum
yields. Herein we report the investigation of both the optical
and electronic properties from the theoretical point of view
for this system. To investigate the substituent effects, several
1,4-bis(2-substituted-1,3,4-oxadiazole)benzene derivatives
(2–6) with different heterocyclic or phenyl groups, as shown
in Scheme 1, have been designed to provide a demonstration
for the rational design of new candidates for luminescent
and electron transport materials for OLEDs.
2. Computational methods
All calculations have been performed using the Gaussian 09
package (Frisch et al., 2009). Optimizations have been carried
out without symmetry constraints. In our previous study, the
B3LYP functional was successfully employed to calculate
charge transport parameters for 1,3,4-oxadiazole derivatives
(Jin and Zhang, 2011). Recently, the same functional was
Scheme 1 Geometries of the derivatives of 1,4-bis(2-substituted-1,3,4-oxadiazole)benzene, along with atom numbering.
Please cite this article in press as: Sun, F., Jin, R. DFT and TD-DFT study on the optical and electronic properties of derivatives of 1,4-bis(2-
substituted-1,3,4-oxadiazole)benzene. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.11.037
successfully used to calculate the charge transport parameters
for OLEDs’ materials (Irfan and zhang, 2009; Liu et al., 2008).
For these reasons, the geometries of 1–6 in ground states (S0)
have been optimized by using the hybrid B3LYP functional
with 6–31G(d) basis set. The structures in the first excited sin-
glet states (S1) for 1–6 have been optimized at the TD-B3LYP
level using the 6-31G(d) basis set. The harmonic vibrational
frequency calculations using same methods as for the geometry
optimizations were used to ascertain the presence of a local
minimum. Absorption and fluorescence spectra of 1–6 have
been predicted using the TD-PBE0/6-31 + G(d,P) method
based on the S0 and S1 optimized geometries, respectively.
The DMF solvent effect also has been considered using the
Polarized Continuum Model (PCM) (Foresman et al., 1992).
The charge transfer rate can be described by Marcus theory
(Marcus, 1993 and Marcus, 1964) via the following equation:
hÞðp=kkB TÞ1=2 expðk=4kB TÞ
K ¼ ðV2 = ð1Þ
where T is the temperature, kB is the Boltzmann constant, k
represents the reorganization energy due to geometric relaxa-
tion accompanying charge transfer, and V is the electronic
coupling matrix element (transfer integral) between the two
adjacent species dictated largely by orbital overlap. It is clear
that two key parameters are the reorganization energy and
electronic coupling matrix element, which have a dominant im-
pact on the charge transfer rate, especially the former. In this
paper, we focus on their reorganization energies k to investi-
gate their charge transport properties. Generally, the k can
be divided into two parts, external reorganization energy (kext)
and internal reorganization energy (kint). The kext represents
the effect of polarized medium on charge transfer; on the other
hand, kint is a measure of structural change between ionic and
neutral states (Lemaur et al., 2005; Hutchison et al., 2005). Our
designed molecules are used as charge transport materials for
OLEDs in the solid film; the dielectric constant of the medium
for the molecules is low. The computed values of the external
reorganization energy in pure organic condensed phases are
not only small but also are much smaller than their internal
counterparts (Cheung and Troisi, 2010; Martinelli et al.,
2010). The reorganization energy could be an important factor
that governs the mobility of charge carriers (Berlin et al.,
2003). Therefore, we only pay attention to the discussion of
the kint of the isolated active organic systems due to ignoring
any environmental relaxation and changes in this paper. The
reorganization energy for electron (ke) and hole (kh) of the
molecules have been predicted from the single point energy
Study on properties of 1,4-bis(2-substituted-1,3,4-oxadiazole)benzene derivatives 3

at the B3LYP/6-31G(d,p) level based on the B3LYP/6-31G(d)

optimized neutral, cationic, and anionic geometries. Hence, the
reorganization energies for ke and kh transfer can be defined as
(Start, 1997):
ke ¼ ðE  0 0
0  E Þ þ ðE  E0 Þ ð2Þ

kh ¼ ðEþ þ 0 0
0  Eþ Þ þ ðEþ  E0 Þ ð3Þ
where Eþ 
0 ðE0 Þ is the energy of the cation (anion) calculated
with the optimized structure of the neutral molecule. Similarly,
Eþ 
þ ðE Þ is the energy of the cation (anion) calculated with the
optimized cation (anion) structure, E0þ ðE0 Þ is the energy of the
neutral molecule calculated at the cationic (anionic) state. Fi-
nally, E00 is the energy of the neutral molecule at the ground
state.
To predict the stability of 1–6 from a viewpoint of molecu-
lar orbital theory, the absolute hardness, g, of 1–6 was calcu-
lated using operational definitions (Cornard and Lapouge,
2006) given by equations below:
   
1 @l 1 @2E IP  EA
g¼ ¼ ¼ ð4Þ
2 @N 2 @N2 2
where l is the chemical potential and N is the total electron
number. The values for adiabatic ionization potential (IP)
and adiabatic electron affinity (EA) of the molecules were cal-
culated as described in the equations below:
IP ¼ EðMþ Þ  EðM0 Þ ð5Þ Figure 1 The HOMOs and LUMOs of 1–6 in S0 states at the
B3LYP/6-31G(d,p) level.
EA ¼ EðM0 Þ  EðM Þ ð6Þ
0 + 
where E(M ), E(M ), and E(M ) are the total energies of the
charge-transfer character of the vertical S0 fi S1 transition. It
neutral, cationic, and anionic forms of the molecules at the
is well known that the photophysical properties of intramolec-
B3LYP/6-31G(d) level, respectively.
ular charge transfer are highly dependent on the electron do-
nor/acceptor strength [34]. Analysis of the FMOs for 1–6
3. Results and discussion indicates that the excitation of the electron from the HOMO
to the LUMO leads the electronic density to flow mainly from
3.1. Electronic transition the side groups to the two 1,3,4-oxadiazole and benzene rings.

The origin of the geometric difference introduced by excitation
can be explained, at least in qualitative terms, by analyzing the
change in the bonding character of the orbital involved in the
electronic transition for each pair of bonded atoms (Forés
et al., 1999). It is useful to examine the frontier molecular orbi-
tals (FMOs) of the compounds under investigation. The qual-
itative molecular orbital representations of the highest
occupied molecular orbitals (HOMOs) and the lowest unoccu-
pied molecular orbitals (LUMOs) for 1–6 in S0 are shown in
Fig. 1. When the HOMO fi LUMO transition involves the
loss of the bonding character of a bond (or the gain of anti-
bonding character), the bond concerned is lengthened and vice
versa. As shown in Fig. 1, both the HOMOs and LUMOs have
p symmetry. The S0 fi S1 excitation process can be mainly as-
signed to HOMO fi LUMO transition, which corresponds to
a p fi p* excited singlet state. One can see that the HOMOs
and LUMOs are delocalized on the whole conjugated mole-
cules for investigated compounds as shown in Fig. 1. It indi-
cates that the spatial overlap between the HOMO and
LUMO is strong, which may result in stronger optical absorp-
tion corresponding to the transition from HOMO to LUMO.
Furthermore, the distribution patterns of HOMOs and
LUMOs also provide a remarkable signature for the
3.2. Spectral simulation
TD-PBE0/6-31 + G(d,p) has been used on the basis of the
optimized geometry to obtain the nature and the energy of
the electronic transitions of 1–6. Table 1 presents the absorp-
tion wavelengths (kabs), the oscillator strength (f), the main
assignment, and excitation energies (E) of 1–6. As shown in
Table 1, the predicted kabs values of 1 both in gas phase and
in DMF are in excellent agreement with experimental results
(Chen et al., 2007), with the maximum deviation being 25
and 28 nm (2392 and 2656 cm1), respectively. As mentioned
above, the transitions correspond to the excitation from the
HOMO to LUMO. Inspection of Table 1 reveals clearly that
the kabs values of 2–4 are similar to that of 1, the deviations
are 2, 6, and 4 nm (178, 522, and 350 cm1), respectively.
The kabs values of 5 and 6 have slight bathochromic shifts com-
pared with that of 1, the deviations being 22 and 32 nm (1829
and 2588 cm1), respectively. It suggests that the 4-pyridyl,
phenyl, and 2-pyrazine substitutions do not significantly affect
the absorption spectra, while the 2-thiophene and 2–1H-pyr-
role substitutions show bathochromic shifts compared with
that of 1. Moreover, we find in Table 1 that the f values of
2–6 are similar to that of 1 except the f value of 6 which is

Please cite this article in press as: Sun, F., Jin, R. DFT and TD-DFT study on the optical and electronic properties of derivatives of 1,4-bis(2-
substituted-1,3,4-oxadiazole)benzene. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.11.037
4 F. Sun, R. Jin

An electronic excitation results in some electron density

Table 1 Calculated maximum absorption wavelengths kabs (in
redistribution that affects the molecules. Changes in the bond
nm), the oscillator strength f, main assignments (coefficient),
lengths in the excited states with respect to their ground state
and excitation energies E (in eV) of 1–6 at the TD-PBE0/6-
geometries can be ascribed to the changes in bonding charac-
31G(d,p)//B3LYP/6-31G(d) level, along with available exper-
ter. Comparing the geometry of 1 in S0 with that in S1 state
imental data.
(for atoms labeling, see Scheme 1), the bond lengths of C2–
Compounds Main assignment E kabs f Exp C3, C5–C6, C1–C7, C4–C12, N8–N9, and N13–N14 are short-
1 HfiL (0.66) 3.63 336 (339)a 1.43 311b ened, while the corresponding bond lengths of C1–C2, C1–C6,
2 HfiL (0.66) 3.71 334 (338) 1.44 C3–C4, C4–C5, C7–N8, C10–N9, C12–N13, and C15–N14 are
3 HfiL (0.66) 3.63 342 (346) 1.40 stretched. Furthermore, the dihedral angles between 2-pyridyl
4 HfiL (0.66) 3.64 340 (345) 1.46 and 1,3,4-oxadiazole rings and between benzene and 1,3,4-oxa-
5 HfiL (0.66) 3.46 358 (365) 1.39 diazole rings in both S0 and S1 are almost 0 or ±180. It sug-
6 HfiL (0.67) 3.37 368 (384) 1.22
gests stronger coupling among the 2-pyridyl, 1,3,4-oxadiazole,
a
Data in parenthesis were obtained considering PCM solvent and benzene rings in 1. Similar phenomena are found for 2–6.
effects. It indicates stronger coupling among the side groups, 1,3,4-
b
Experimental data for 1 in DMF solvent from Chen et al. oxadiazole, and benzene rings. As a consequence, the electron
(2007).
can move more fluently from the electron-donating side groups
to the two 1,3,4-oxadiazole and benzene rings. Therefore, the
intramolecular charge transfer transition for 1–6 in S1 becomes
slightly lower than that of 1. The oscillator strength for an elec- much easier than those in S0, resulting in the bathochromic
tronic transition is proportional to the transition moment. In shift in their fluorescence spectra compared with their absorp-
general, larger oscillator strength corresponds to larger exper- tion spectra.
imental absorption coefficient or stronger fluorescence inten-
sity. The results displayed in Table 1 reveal that 2–6 3.3. Charge transport property and stability
correspond to intensive spectra as 1.
Table 2 presents fluorescence wavelengths (kfl), the oscilla- The calculated reorganization energies for hole and electron
tor strength (f), main assignments (coefficient), and excitation are listed in Table 3. It is well-known that the lower the reor-
energies (E) of 1–6 at the TD-PBE0/6-31G(d,p) level. As listed ganization energy values, the higher the charge transfer rate
in Table 2, the predicted kfl values of 1 both in gas phase and in (Ran et al., 2009; Zou et al., 2008). The reorganization energies
DMF are in agreement with experimental results (Chen et al., calculated for hole kh of 3 and 6 are smaller than that of N,N0 -
2007), with the maximum deviation being 28 and 35 nm (1932 diphenyl-N,N0 -bis(3-methlphenyl)-(1,10 -biphenyl)-4,40 -diamine
and 2372 cm1), respectively. There is little change in emission (TPD) which is a typical hole transport material kh = 0.290 eV
spectra data compared with 1 either. The kfl values of 5 and 6 (Gruhn et al., 2002). This implies that the hole transfer rates of
show slight bathochromic shifts 21 and 20 nm (1278 and 3 and 6 might be higher than that of TPD. Thus, 3 and 6 could
1220 cm1) in gas phase compared with that of 1, while the be hole transport materials from the stand point of the smaller
corresponding values of 2–4 are similar to that of 1, the devi- reorganization energy. The ke values of 2–5 are smaller than
ations are 4, 1, and 3 nm (259, 63, and 190 cm1), respectively. that of tris(8-hydroxyquinolinato)aluminum(III) (Alq3), which
The f values of kfl for 2–5 are similar to that of 1, while the f is a typical electron transport material ke = 0.276 eV (Marcus,
value of 6 is less than that of 1. Our results suggest that the 1964). This indicates that their electron transfer rates might be
substituted derivatives have the same optical properties as par- higher than that of Alq3. The ke values of 2–5 are smaller than
ent molecule 1, which implicated a new series of luminescent those of their kh values, suggesting that the carrier mobility of
materials for OLEDs. the hole is larger than that of the electron. Hence, 2–5 can be
used as promising electron transport materials in the OLEDs
from the stand point of the smaller reorganization energy. In
addition, the difference between the ke and kh values for 3 is
Table 2 Calculated maximum fluorescence wavelengths kfl (in 0.035 eV, implying that 3 has better equilibrium properties
nm), the oscillator strength f, main assignments (coefficient), for hole- and electron-transport. Therefore, 3 may be used as
and excitation energies E (in eV) of 1–6 at the TD-PBE0/6- good candidate for ambipolar charge transport material.
31G(d,p)//TD-B3LYP//6-31G(d) level, along with available
experimental data.
Compounds Main assignment E kfl f Expb
1 H‹L (0.70) 3.14 395 (402)a 1.60 367b Table 3 Calculated molecular ke, kh, and g (all in eV) of 1–6 at
2 H‹L (0.70) 3.17 391 (400) 1.62
the B3LYP/6-31G(d,p) level.
3 H‹L (0.70) 3.13 396 (405) 1.60
4 H‹L (0.70) 3.12 398 (408) 1.64 Compounds kh ke g
5 H‹L (0.70) 2.98 416 (428) 1.59 1 0.304 0.281 3.082
6 H‹L (0.70) 2.99 415 (435) 1.42 2 0.307 0.270 3.109
a 3 0.275 0.240 3.062
Data in parenthesis were obtained considering PCM solvent
effects. 4 0.298 0.260 3.057
b 5 0.308 0.233 2.949
Experimental data for 1 in DMF solvent from Chen et al.
(2007). 6 0.269 0.299 2.941

Please cite this article in press as: Sun, F., Jin, R. DFT and TD-DFT study on the optical and electronic properties of derivatives of 1,4-bis(2-
substituted-1,3,4-oxadiazole)benzene. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.11.037
Study on properties of 1,4-bis(2-substituted-1,3,4-oxadiazole)benzene derivatives
Figure 2 Electrostatic surface potentials for 1–6. Regions of higher electron density are shown in red and of lower electron density in
blue (values in atomic units).
As the stability is a useful criterion to evaluate the nature of
devices for charge transport and luminescent materials, the g
values of investigated molecules were calculated and shown
in Table 3. The g is the resistance of the chemical potential
to change in the number of electrons. Inspection of Table 3 re-
veals clearly that the g values of 2–6 are similar to that of 1,
indicating that the stabilities of 2–6 are equal to that of 1. Fur-
thermore, the electrostatic surface potentials (Irfan and zhang,
2009) of investigated molecules were calculated as shown in
Fig. 2. As shown in Fig. 2, the partial negative charges are
on the 1,3,4-oxadiazole ring while the partial positive charges
are on the phenyl and two side fragments for 1–6. The profiles
of electron densities of 2–6 are similar to that of 1, implying
that the substitution effect does not significantly affect the sta-
bility of the substituted derivatives. These results show qualita-
tive agreement with the results based on the absolute hardness.
4. Conclusion
Our computational results predicted the electronic and optical
properties for a number of newly designed 1,4-bis(2-substi-
tuted-1,3,4-oxadiazole)benzene derivatives. On the basis of
the equilibrium geometries, the effect of the substitution on
the absorption and emission spectra is evaluated for the substi-
tuted derivatives, confirming a new set of candidates for emit-
ting materials. The FMO analysis has turned out that the
vertical electronic transitions of absorption and emission of
1,4-bis(2-substituted-1,3,4-oxadiazole)benzene derivatives are
characterized as intramolecular charge transfer. The study of
substituent effect by introducing different heterocyclic or phe-
nyl groups revealed that the substitution effect does not signif-
icantly affect the stability of the substituted derivatives. Both
kabs and kfl of the derivatives with 2-thiophene and 2-1H-pyr-
role fragments show bathochromic shifts compared with par-
ent compound 2-pyridyl substituted derivative (1), while the
corresponding values of the substituted derivatives with 4-pyr-
idyl, 2-pyrazine, and phenyl fragments are similar to that of
parent compound 1. Our results suggest that the substituted
derivatives with 4-pyridyl, 2-pyrazine, phenyl, 2-thiophene,
and 2-1H-pyrrole fragments are expected to be promising can-
didates for luminescent materials for OLEDs. Furthermore,
the substituted derivatives with 4-pyridyl, 2-pyrazine, phenyl,
and 2-thiophene fragments can be used as promising electron
transport materials, while the substituted derivatives with 2-
pyrazine and 2-1H-pyrrole fragments can be used as promising
Please cite this article in press as: Sun, F., Jin, R. DFT and TD-DFT study on the optical and electronic properties of derivatives of 1,4-bis(2-
substituted-1,3,4-oxadiazole)benzene. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.11.037
5
hole transport materials. In addition, the substituted derivative
with 2-pyrazine fragment may be used as good candidate for
ambipolar charge transport material for OLEDs.
Acknowledgments
Financial support from the Natural Science Foundation of In-
ner Mongolia Autonomous Region (2011ZD02) is gratefully
acknowledged.
Appendix A. Supplementary data
Supplementary data associated with this article can be found,
in the online version, at http://dx.doi.org/10.1016/
j.arabjc.2013.11.037.
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Please cite this article in press as: Sun, F., Jin, R. DFT and TD-DFT study on the optical and electronic properties of derivatives of 1,4-bis(2-
substituted-1,3,4-oxadiazole)benzene. Arabian Journal of Chemistry (2013), http://dx.doi.org/10.1016/j.arabjc.2013.11.037