4,5,9,10-Pyrene Diimides: A Family of Aromatic Diimides Exhibiting High Electron Mobility and Two-Photon Excited Emission

Article abstract of DOI:10.1002/anie.201707529

The design and synthesis of high-performance n-type organic semiconductors are important for the development of future organic optoelectronics. Facile synthetic routes to reach the K-region of pyrene and produce 4,5,9,10-pyrene diimide (PyDI) derivatives are reported. The PyDI derivatives exhibited efficient electron transport properties, with the highest electron mobility of up to 3.08 cm² V^?1 s^?1. The tert-butyl-substituted compounds (t-PyDI) also showed good one- and two-photon excited fluorescence properties. The PyDI derivatives are a new family of aromatic diimides that may exhibit both high electron mobility and good light-emitting properties, thus making them excellent candidates for future optoelectronics.

Full text of DOI:10.1002/anie.201707529

A Journal of the Gesellschaft Deutscher Chemiker
Angewandte
International Edition Chemie
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Accepted Article
Title: 4,5,9,10-Pyrene Diimides: A New Family of Aromatic Diimides
Exhibiting High Electron Mobility and Two-Photon Excited
Emission
Authors: Ze-Hua Wu, Zhuo-Ting Huang, Rui-Xue Guo, Chun-Lin
Sun, Li-Chuan Chen, Bing Sun, Zi-Fa Shi, Xiangfeng Shao,
Hanying Li, and Hao-Li Zhang
This manuscript has been accepted after peer review and appears as an
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to ensure accuracy of information. The authors are responsible for the
content of this Accepted Article.
To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.201707529
Angew. Chem. 10.1002/ange.201707529
Link to VoR: http://dx.doi.org/10.1002/anie.201707529
http://dx.doi.org/10.1002/ange.201707529

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COMMUNICATION
4
,5,9,10-Pyrene Diimides: A New Family of Aromatic Diimides Ex-
hibiting High Electron Mobility and Two-Photon Excited Emission
[a]
[c]
[a]
[a]
[a]
[a]
Ze-Hua Wu , Zhuo-Ting Huang , Rui-Xue Guo , Chun-Lin Sun , Li-Chuan Chen , Bing Sun , Zi-Fa
Shi , Xiangfeng Shao , Hanying Li* and Hao-Li Zhang* [a], [b]
[a]
[a]
[c]
2
-1 -1
Abstract: Design and synthesis of high performance n-type organic
semiconductors are important for the development of future organic
optoelectronics. Herein, we report the facile synthetic routes to reach
the K-region of pyrene and produce 4,5,9,10-pyrene diimide (PyDI)
derivatives. The PyDI derivatives exhibited efficient electron
transport properties with the highest electron mobility up to 3.08
molecules have reached 8.6[9] and 10.8[10] cm V s , respectively.
Significant efforts have been made to design new diimide
[
11]
skeleton, including pyromellitic diimides,
(ADI)[
12]
anthracene diimide
and 1,2,5,6-naphthalene diimide[13]
electron motilities of these new diimides have not exceeded 1
. However, the
2
-1 -1
cm V s .
2
-1 -1
cm V s . Besides, the tert-butyl substituted compounds (t-PyDI)
also showed good one and two photon excited fluorescence
properties. The PyDI derivatives are new family of aromatic diimides
that may exhibit both high electron mobility and good light emitting
properties, making them excellent candidates for future
optoelectronics.
Organic semiconductors have attracted considerable
academic and commercial interest in recent years for their
[
1]
potential in constructing low cost, stretchable and solution-
[
2]
processed large-area electronics. In general, the development
of n-type organic semiconductors largely lagged behind the p-
type counterparts, which has limited the development of
practical organic electronics.[3] Large numbers of n-type
semiconductors have been reported in the last few years, which
mostly based on electron deficient frameworks, like perylene
Figure 1. Comparison between the structures of PyDI and other
representative linear aromatic diimides, including NDI, ADI and PDI.
To date, nearly all the small acenes have been used as core
for construction of aromatic diimides, except pyrene. Pyrene
consists of four-ring-fused planar electron enriched skeleton,
which is well known for high photoluminescence efficiency.[
Only until very recently, researchers are able to synthesize
pyrene-based diimide. Pei and colleagues described the
synthesis of 1,2,6,7-pyrene diimde, but no charge transport
property was reported.[15] Yu’s group has employed 4,5,9,10-
pyrene diimide unit in solar cell materials which exhibited the
diimide
(PDI),[4]
naphthalene
diimide
(NDI),[5]
diketopyrrolopyrrole (DPP)[6] and heteroacenes[7] etc. However,
the number of high performance n-type organic semiconductors
is still very limited.[8] Therefore, developing new electron
deficient frameworks for n-type organic semiconductors is of
great importance.
14]
Aromatic diimides are among the most important classes of
n-type organic materials. Classical semiconductors like NDI and
PDI (Fig. 1) derivatives have found wide applications in
optoelectronics. After decades efforts of structural optimization,
the highest electron mobilities from NDI and PDI based small
highest electron mobility of 8×10-4 cm V s in blend.[16] Herein,
we report the first class of pyrene-diimide small molecules
exhibiting excellent charge transport capability and attractive
optical properties. By using two different synthetic routes, we
2
-1 -1
obtained
a series of axisymmetric 4,5,9,10-pyrene diimide
(
PyDI) derivatives. Electron mobility of PyDI derivatives in field
2
-1 -1
effect transistor reached 3.08 cm V s , making them one of the
best classes of diimide-based organic semiconductors.
[a]
Z. H. Wu, R. X. Guo, Dr. C. L. Sun, L. C. Chen, B. Sun, Prof. Z. F.
Shi, Prof. X. F. Shao, and Prof. H. L. Zhang
State Key Laboratory of Applied Organic Chemistry
Key Laboratory of Special Function Materials and Structure Design
College of Chemistry and Chemical Engineering
Lanzhou University, Lanzhou 730000 (P. R. China)
E-mail: haoli.zhang@lzu.edu.cn
Previous researches [13, 17] have revealed that axisymmetric
diimides (typically NDI and PDI) are generally preferred due to
desirable intramolecular charge distribution and π-π overlap in
crystals. The ideal positions for constructing axisymmetric
pyrene diimide are the 4,5,9,10-positions (K-region) of pyrene.
However, the main obstacle to the synthesis is that the
electrophilic substitution of pyrene preferentially takes place at
the 1,3,6,8-positions, so that accessing the K-region is difficult.
[
b]
c]
Prof. H. L. Zhang
Tianjin Key Laboratory of Molecular Optoelectronic Sciences
Collaborative Innovation Center of Chemical Science and
Engineering
Tianjin 300072 (P. R. China)
E-mail: haoli.zhang@lzu.edu.cn
[
Ms. Z. T. Huang, Prof. H. Y. Li
To achieve ideal regioselectivity, we developed two feasible
strategies to synthesize the 4,5,9,10-pyrene diimides (PyDI),
which are illustrated in Scheme 1. Route 1 is inspired by Yu's
work[16], which uses 1,2,3,6,7,8-hexahydropyrene as the starting
material and converts the core to pyrene after introducing
diimdes. The main problem with this route is that the
intermediate compounds 1-4 are nearly insoluble in most
State Key Laboratory of Silicon Materials
Key Laboratory of Macromolecule Synthesis and Functionalization
Department of Polymer Science and Engineering
Zhejiang University, Hangzhou 310027 (P. R. China)
E-mail: hanying_li@zju.edu.cn
Supporting information for this article is given via a link at the end of
the document.
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organic solvents, making the processing and characterization
difficult. To overcome the solubility problem, we designed
another synthetic route. Route 2 employs positional protective
tert-butyl groups at the 2,7-positions of pyrene, so that the
diimide units could be introduced to the desired 4,5,9,10
positions. This synthetic route affords 2,7-ditert-butyl-4,5,9,10-
pyrene diimde (t-PyDI) in good yield. In the presence of tert-
butyl groups, the intermediate compounds 5-9 and the product t-
PyDI have excellent solubility in common organic solvents.
Details of the synthesis along with the characterization data are
available in the Supporting Information. In both routes, the alkyl
chains on the nitrogen atoms can be easily varied by using
different amines as reactants. In the following discussion, we will
distance between the adjacent pairs is around 7.349 Å. The
large separation between the adjacent pairs may hinder charge
transport, but such lamellar motif and twisted conformation could
be beneficial for solid state light emission.[
18]
use the n-pentyl moiety substituted compounds, named as C
5
-
PyDI and t-C -PyDI, as the typical examples, while the
5
properties of the other compounds are provided in the
Supporting Information.
Figure 2. Single crystal structure (a), top view (b) and side view (c) of the
crystal packing diagram of C -PyDI. Single crystal structure (d), top view (e)
5
and side view (f) of the crystal packing diagram of t-C
5
-PyDI. Hydrogen atoms
are omitted for clarity.
0
eV-
1
-2
-3
-4
-5
-6
-7
-8
LUMO
HOMO
Scheme 1. Synthetic routes to PyDI and t-PyDI
The single crystal X-ray diffraction (XRD) (Fig. 2) shows that
the C
5
-PyDI crystalizes into triclinic system with P-1 space group,
t-PyDI PyDI
5
6
7
9
in which the molecule adopts a rigid and planar conformation
with 1-D π-stacking motif. The closest planar distance of the
nearest molecules is 3.414 Å indicating strong π-π interactions,
Figure 3. An illustration of the frontier molecular orbitals of the compounds 5,
6, 7, 9, t-PyDI and PyDI.
which is favourable for charge transport. In contrast, the t-C
PyDI crystalizes into monoclinic system with P 2/c space group.
In the crystals, the pyrene core of the t-C -PyDI is slightly
twisted to compensate the steric hindrance of the tert-butyl
moieties and to maximize the π-π interactions. As a result, the
molecules pack into a lamellar motif with two neighbouring
molecules forming a pair (Fig. 2f). In each pair, the nearest two
molecules have large π-π overlap with the closest distance
measured to be 3.165 Å. However, each pair is separated from
the neighbouring pair by the n-pentyl chains and the closest
5
-
With the tert-butyl groups providing enough solubility, the
5
change of electronic properties along the route 2 was readily
followed by various spectroscopic and electrochemical
characterizations in solutions. The UV-vis spectra and cyclic
voltammetry curves of the compounds 5, 6, 7, 9, t-C
5
-PyDI and
C
5
-PyDI are shown in Fig. S1 and S2. Table S1 summarizes the
electronic properties of these compounds obtained from cyclic
voltammetry and density functional theory (DFT) calculations
using Gaussian [DFT/B3LYP/6-311+G(d,p)] package. Fig. 3
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compares the energy levels and frontier molecular orbitals of
these compounds. The LUMO energy levels are dramatically
lowered from compounds 5 (-1.69 eV) to 7 (-3.50 eV) due to the
introduction of electron withdrawing groups. Compared with the
area of the emission spectra decreases, indicative of lower FQY
in high concentrations. For instance, when the concentration of
t-C
5
-PyDI changes from 1×10-7 mol/L to 1×10-4 mol/L in
cyclohexane, the FQY reduces from 79.5% to 18.3%.
compound 9, the LUMO energy level of t-C
which is attributed to electron donating effect of the lone pair
electrons on the nitrogen. The HOMO and LUMO levels of C
PyDI decrease 0.23 eV and 0.14 eV, respectively, compared
with t-C -PyDI, due to the hyper conjugation and electron
donating effect of the tert-butyl groups. Fig. 3 clearly illustrates
that by attaching different electron withdrawing groups, the
energy levels of pyrene are systematically tuned.
5
-PyDI raises slightly,
Two photon absorption (TPA) is a process where molecules
can absorb two less energetic photons simultaneously.
Fluorescent molecules with large TPA cross sections may
provide enhanced light penetration, high spatial resolution and
low specimen photo damage in imaging applications.[23] The
5
-
5
dispersion of TPA cross section of C
between 730 nm and 940 nm are shown in Fig. 4b. The
maximum TPA cross section of t-C -PyDI and C -PyDI occur
5 5
-PyDI and t-C -PyDI
5
5
We investigated the fluorescence properties of the C
and t-C -PyDI in both solution and solid states. In diluted
solutions lower than 1×10-7 mol/L, the fluorescence quantum
yield (FQY) of C -PyDI is 59.7%. The t-C -PyDI gives even
higher fluorescence quantum yield of 79.5%. In solid state, the
-PyDI shows a total quench of the fluorescence due to strong
intermolecular interaction in crystals.[19] In contrast, t-C
-PyDI
shows light yellow colour with a fluorescence quantum yield of
5
-PyDI
from 790 nm to 840 nm, which matches well with the optical
window in biological tissue.[24] The highest TPA cross sections of
t-C -PyDI and C -PyDI are 89.15 GM and 40.74 GM,
5 5
respectively, which are sufficient for two photon fluorescence
microscopy imaging applications.[25] In comparison, simple NDI
and PDI have nearly no fluorescence and negligible TPA cross
section in the near-infrared wavelength region.[26] The high TPA
cross sections of PyDI derivatives are attributed to the highly
emissive property and proper length of π system of the pyrene
core.[25]
5
5
5
C
5
5
6.15% in solid.
We found that the n-pentyl and n-hexyl chains appear to be
of the appropriate length for solution processible materials.
Shorter chains give poor solubility, while longer chains, like n-
heptyl chain, induce poor crystallinity and hence very poor
device performance (Fig. S9). Thus, we report herein organic
field effect transistors (OFETs) fabricated based on the crystals
5
2
2
1
1
5
.5x10
.0x10
.5x10
.0x10
.0x10
-7
100
80
a)
1×10 mol/L b)
-
6
t-C -PyDI
1
5
1
5
×10 mol/L
5
5
5
5
4
-6
×10 mol/L
C -PyDI
5
-
5
×10 mol/L
-
5
×10 mol/L
-
4
60
1×10 mol/L
40
of C
-PyDI and t-C
of droplet-pinned crystallization (DPC).
fabrication are described in the Supporting Information. The t-
-PyDI and t-C -PyDI formed narrow and short nano/microrod-
5
5
-PyDI, t-C -PyDI and their n-hexyl substituted analogues
20
C
6
6
-PyDI. Crystals were prepared by the method
[
27]
0
Details of device
0
.0
3
00 400 500 600 700
Wavelength (nm)
750 800 850 900 950
Wavelength (nm)
C
5
6
like single crystals with many branches, and most of the crystals
did not bridge across the channel between source and drain
electrodes (S-D electrodes) (Fig. S9). While for C -PyDI and C -
5 6
PyDI the crystal ribbons were much longer and wider and
arranged on the substrate regularly (Fig. 5), favouring charge
transport.[28]
Figure 4. Emission spectra of t-C
The spectra are blanked in the range of 520-560 nm in order to remove the
second order diffraction peak of excitation light) (a). Dispersion of two photon
absorption cross section of t-C -PyDI and C -PyDI in chloroform (b).
5
-PyDI in cyclohexane excited at 270 nm
(
5
5
The polarized-light micrograph (Fig. S12) and selected area
The formation of pyrene excimer is an important
phenomenon which can be used in designing fluorescent
labelled probes and biosensors.[20] Recently, Pei[15] and Köhler[21]
have reported formation of excimer in pyrene-based small
molecules and polymers, respectively. The excimer formation of
electron diffraction (SAED) patterns (Fig. S13) of the C
and C -PyDI nano-ribbons support their single-crystalline nature.
SAED patterns indicate that the molecular packing within the
nano-ribbons of C -PyDI and C -PyDI are identical to those in
5
-PyDI
6
5
6
the single crystal. Furthermore, the transmission electron
microscopy (TEM) and SAED identify that [010] is the preferable
t-C
emission spectra under different concentrations (C
not studied due to poor solubility). In the low concentration of
×10-7 mol/L, two structural fluorescence bands peaked at 307
and 352 nm emerges. When the concentration gradually
5
-PyDI (Fig. 4a) in cyclohexane was studied by recording the
5
-PyDI was
growth direction of the crystal ribbons of C
The X-ray diffractions from the DPC films of C
and t-C -PyDI are shown in Fig. S14. The XRD peaks of the
films of -PyDI and -PyDI correspond to the (001)
diffractions as derived from the single crystal structure. However,
the XRD of t-C -PyDI shows a broad diffraction band around
25 degree with low intensity, indicating poor-crystallinity.
5
-PyDI and C
6
-PyDI.
5
-PyDI, C
6
-PyDI
1
5
C
5
C
6
-6
increases to 1×10 mol/L, a new broad band appears at 480 nm.
The unstructured emission band at 480 nm is attributed to the
formation of excimer.[22] The emergence of the new band is
accompanied by the decrease of the bands at low wavelength.
Further increasing the concentration to 1×10-4 mol/L, the
emission bands of monomer disappear, with an isostilbic point at
5
~
Based on these aligned single crystals, FETs were
constructed by depositing a layer of 70 nm Au as the source and
drain electrodes in the bottom-gate and top-contact configuration.
435 nm. Meanwhile, as the concentration increases, the integral
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COMMUNICATION
The transfer and output characteristic curves of t-C
5
-PyDI, C
5
-
T
the on/off ratios and threshold voltage (V ) are shown in Table 1,
PyDI and C
shows no mobility.
6
-PyDI (Fig. S11) were tested in glove box. t-C
6
-PyDI
where each average value was obtained from more than 20
working devices on 8 different substrates. Further optimization
5 6
was performed on the OFET devices of C -PyDI and C -PyDI
using Ag electrodes, which has a lower work function than Au.
The conditions of crystals’ growth were maintained as above for
comparison. When using Ag as the S-D electrodes, the highest
-
4
-3
-3
-3
1
1
1
1
1
1
0
0
0
0
0
0
6.0x10
0V
V
G
a)
b)
-5
c)
1.8x10
1.5x10
-
-
6
6
20V
40V
60V
80V
5.0x10
4.0x10
3.0x10
-
-
-
-
6
7
8
9
100V
120V
1.2x10-6
2
-1 -1
e
5 6
μ of C -PyDI and C -PyDI increases to 3.08 cm V s and 2.36
-
3
3
-7
2
-1 -1
9.0x10
cm V s , respectively.
-
2.0x10
-7
6.0x10
-
10
11
-3
-7
1
0
0
1.0x10
3.0x10
PyDI is the first class of pyrene diimide framework that
-
1
0.0
0.0
enables efficient charge transport. The highest electron mobility
0
20 40 60 80 100120
VG (V)
0
20 40 60 80 100 120
DS (V)
V
2
-1 -1
of
C
5
-PyDI reached up to 3.08 cm V s , which has
-
4
1
0
0
0
0
0
0
-5
-
-
-
-
-
-
3
2.4x10
0V VG
outperformed most of the reported diimides.[3b,
4-5, 11-13]
d)
e)
-5
3.0x10
2.5x10
2.0x10
1.5x10
1.0x10
f)
20V
1
1
1
1
1
40V
60V
80V
100V
120V
3
3
3
3
4
2.0x10-5
-
-
-
-
6
7
8
9
5
Meanwhile, the t-C -PyDI molecules exhibited lower electron
-5
1.6x10
mobility but higher one and two photon excited fluorescence
emission properties. This work illustrates that the PyDI
framework can be an excellent platform for designing new n-type
organic semiconductors with high electron mobility and good
one and two photon excited light emitting properties. It is
expected that further structural modification to the PyDI skeleton
could give even higher performance. The PyDI semiconductor
family may find more practical applications in the future
optoelectronics.
-5
1.2x10
-6
8.0x10
-
10
11
5.0x10
-6
1
0
0
4.0x10
-
0.0
1
0.0
0
20 40 60 80 100120
VG (V)
0
20 40 60 80100120
VDS (V)
Figure 5. The optical microscopy (OM) image of the crystals (a), typical
transfer (b) and output characteristics curves (c) of C -PyDI. The OM image of
the crystals (d), typical transfer (e) and output characteristics curves (f) of C
PyDI. (Ag was used as electrode).
5
6
-
Acknowledgements
5 5 6
Table 1. OFET performance data for t-C -PyDI, C -PyDI and C -PyDI
crystals.
This work is supported by the Ministry of Science and
Technology of China (2017YFA0204903), National Natural
Science Foundation of China (NSFC. 51525303, 21233001,
Compound
S-D
Electrode
Mobility
[cm V s ]
on/off
ratio
T
V (V)
2
-1 -1 [a]
2
1572086, 51625304, 21522203), 111 Project. The authors
-
4
>103
t-C
5
-PyDI
Au
2.51×10
49-60
thank beam line BL14B1 (Shanghai Synchrotron Radiation
Facility) for providing the beam time.
-
5
-5
(
8.72×10 ±0.91×10 )
Ag
Au
Ag
Au
Ag
-
-
-
Keywords: pyrene • diimide • organic semiconductors • two
photon absorption • electron transport
C
C
5
-PyDI
-PyDI
0.46(0.19±0.13)
3.08(1.92±0.19)
0.51(0.29±0.12)
2.36(2.05±0.17)
>106
>106
43-50
45-62
45-60
49-68
[
[
1]
2]
T. Someya, Z. Bao, G. G. Malliaras, Nature 2016, 540, 379-385.
M. R. Niazi, R. Li, M. Abdelsamie, K. Zhao, D. H. Anjum, M. M. Payne,
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>106
6
>106
2371-2378.
[
3]
a) H. Klauk, U. Zschieschang, J. Pflaum, M. Halik, Nature 2007, 445,
[
a] The values in the parentheses represent average mobility ± standard
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deviation.
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[
[
4]
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11998.
The field effect mobility (μ) was calculated in the saturation
2
regime with the equation: IDS=μC
0
(W/2L)(V
G
T
–V ) , where the IDS
M. A. Kobaisi, S. V. Bhosale, K. Latham, A. M. Raynor, S. V. Bhosale,
Chem. Rev. 2016, 116, 11685-11796.
is the current of S-D electrodes, μ is the field effect mobility, W
and L are the width and length of the channel. The drop casted
crystalline ribbons only partially covered the channel region.
Therefore, the W and L were measured instead of using the
J. Lee, A. R. Han, J. Kim, Y. Kim, J. H. Oh, C. Yang, J. Am. Chem. Soc.
2012, 134, 20713-20721.
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channel dimensions of the shadow mask (Fig. S10). C
gate dielectric capacitance. The divinyltetramethyldisiloxane
bis(benzocyclobutene) (BCB) covered SiO /Si substrates
is the gate voltage
is the threshold voltage. All the devices exhibited n-type
0
is the
[
G. Xue, J. Wu, C. Fan, S. Liu, Z. Huang, Y. Liu, B. Shan, H. L. Xin, Q.
Miao, H. Chen, H. Li, Mater. Horiz. 2016, 3, 119-123.
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-8
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Pflaum, X. Tao, J. Brill, F. Würthner, Nat. Commun. 2015, 6, 5954.
showed the capacitance of 1.1×10 F. V
and V
behaviour. The highest electron transport mobility (μ
G
T
[
[
10] N. A. Minder, S. Ono, Z. Chen, A. Facchetti, A. F. Morpurgo, Adv.
Mater. 2012, 24, 503-508.
e
) of t-C
5
-
2
-1 -1
2
-
PyDI, C
5
-PyDI and C
6
-PyDI were 2.5×10-4 cm V s , 0.46 cm V
11] Q. Zheng, J. Huang, A. Sarjeant, H. E. Katz, J. Am. Chem. Soc. 2008,
130, 14410-14411.
1
-1
2
-1 -1
s
and 0.51 cm V s , respectively. Together with the mobility,
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[
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Angewandte Chemie International Edition
10.1002/anie.201707529
COMMUNICATION
COMMUNICATION
Ze-Hua Wu, Zhuo-Ting Huang, Rui-Xue
Guo, Chun-Lin Sun, Li-Chuan Chen,
Bing Sun, Zi-Fa Shi, Xiangfeng Shao,
Hanying Li* and Hao-Li Zhang*
Page No. – Page No.
4
,5,9,10-Pyrene Diimides: A New
Text for Table of Contents
Family of Aromatic Diimides Ex-
hibiting High Electron Mobility and
Two-Photon Excited Emission
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