DOI: 10.1039/C4CC04778H
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ChemComm
registered. The spectrum is similar to those reported for other
involving its reduction and substitution with alkoxy solubilizing
groups. Self-assembling capabilities of P-C8 and its interesting
luminescent and optoelectronic properties should be pointed out.
This research was carried out in the framework of the project
7
g,9,20
azaacenes
and consistent with the calculated transition. (see
Figure 3 and Table S3 in Supplementary Information). The lowest
energetic band (at 489 nm) is an intramolecular CT band
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0
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5
associated with DA interactions involving charge transfer 60 entitled “New solution processable organic and hybrid
between the HOMO localized on the anthracene parts of the
molecule and the LUMO located on the phenazine central part. It
is worth noting that the HOMO-LUMO transition is highly
privileged due to the symmetry of the molecule being restricted to
(organic/inorganic) functional materials for electronics,
optoelectronics and spintronics” (Contract No. TEAM/2011-8/6),
which is operated within the Foundation for the Polish Science
Team Programme cofinanced by the EU European Regional
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3
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the centrosymmetric (C
i
) point group. Since HOMO and LUMO 65 Development Fund. The Gaussian 09 calculations were carried
belong to A and A irreducible representations, respectively, the
g
u
out in the Wroclaw Centre for Networking and Supercomputing,
WSCC, Wroclaw, Poland, http://www.wcss.wroc.pl, under
calculational Grant No. 283.
transition between them is highly privileged according to the
Laporte selection rule. For full analysis of the electronic
transitions natural transition orbitals analysis was performed and
included to Supplementary Information.
Notes and references
Finally, a difference of 0.41 eV between the optical and
electrochemical band gaps should be pointed out. This is mainly
associated with the exciton binding energy which in some organic
compounds may reach values up to 0.5 eV.21
a
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Faculty of Chemistry, Warsaw University of Technology Noakowskiego
, 00-664 Warsaw, Poland. E-mail: piotrbujakchem@poczta.onet.pl
3
b
Institute of Physical Chemistry, Polish Academy of Science, Kasprzaka
44/52, 01-224 Warsaw, Poland
c
Department of Molecular Physics, Technical University of Lodz,
P-C8 is photoluminescent, emitting green light with
a
-
1
75 Zeromskiego 116, 90-924 Lodz, Poland
Electronic Supplementary Information (ESI) available: Experimental
relatively low Stokes shift of 881 cm (22 nm) (see Figure 3).
The measured high photoluminescence quantum yield (56%)
together with its short lifetime (3.9 ns) prompted us to apply this
derivative as an active component of “guest – host” type organic
light emitting diodes. In Figure 4 the electroluminescence
spectrum of 1 wt.% molecular dispersion of P-C8 in a two
component matrix consisting of hole transporting poly(9-
vinylcarbazole) (PVK) and electron transporting 2-(4-
biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD) is
compared with the spectrum of the pure matrix. It is clear that the
Förster energy transfer is efficient and complete since the
spectrum is characteristic of P-C8 with no features originating
from the matrix (PVK + PBD). This is assured by a strong
overlap the P-C8 absorption spectrum with the emission
spectrum of the matrix.
†
procedures, characterization data of P-C8, organic light emitting diode
fabrication. CCDC 1006274. For ESI and crystallographic data in CIF see
DOI: 10.1039/b000000x/
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Figure 4. Electroluminescence spectra of: 1 wt% dispersion of P-C8 in
PVK+PBD matrix (red line) and pure PVK+PBD matrix (blue line). The
inset shows the zoom of the P-C8 electroluminescence spectrum over
narrower spectral range.
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following
structure
ITO/PEDOT:PSS/PVK+1wt%
P-
8
9
2
115
5
0
C8+PBD/LiF/Al yield luminance exceeding 250 cd/m and
luminous efficiency of 1.0 cd/A (for details see supplementary
information).
To summarize, we have demonstrated that indanthrone, an old
insoluble dye, can be transformed into an interesting, solution 120
processable semiconductor through a one-step, one pot process
K. Goto, R. Yamaguchi, S. Hiroto, H. Ueno, T. Kawai, H.
Shinokubo, Angew. Chem., Int. Ed., 2012, 51, 10333.
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