Nondoped deep-blue spirofluorenexanthene-based green organic semiconductors (GOS) via a pot, atom and step economic (PASE) route combining direct arylation with tandem reaction

Article abstract of DOI:10.1039/c4tc01963f

Effective synthesis of organic semiconductors with pot, atom, and step economic (PASE) methods will be an indispensable part of green electronics. In this paper, we combined direct arylation with one-pot/tandem reaction to synthesize a green organic semiconductor (GOS), di(spiro[fluorene-9,9′-xanthene]-2-yl)-1,2,4,5-tetrafluorobenzene (DSFX-TFB), serving as the emitting layer for organic light-emitting devices (OLEDs). The maximum current efficiency (CE) of 3.2 cd A^-1, power efficiency (PE) of 2.0 lm W^-1 and external quantum efficiency (EQE) of 4.1% were obtained with the CIE coordinates (0.15, 0.08) in the nondoped deep-blue OLEDs. Meanwhile, good energy transfer and device performances with maximum CE of 8.03 cd A^-1 and PE of 4.62 lm W^-1 were achieved in typical sky-blue fluorescent OLEDs using DSFX-TFB as host and p-bis(p-N,N-diphenyl-aminostyryl)benzene (DSA-Ph) as dopant material. This work provides a PASE synthetic route for GOSs and eco-friendly materials.

Full text of DOI:10.1039/c4tc01963f

Journal of
Materials Chemistry C
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PAPER
Nondoped deep-blue spirofluorenexanthene-
based green organic semiconductors (GOS) via a
pot, atom and step economic (PASE) route
Cite this: J. Mater. Chem. C, 2015, 3, 94
combining direct arylation with tandem reaction†
a
c
b
a
a
Ming-Li Sun, Wen-Sai Zhu, Zhen-Song Zhang, Chang-Jin Ou, Ling-Hai Xie,*
c
a
b
ac
Yang Yang, Yan Qian, Yi Zhao and Wei Huang*
Effective synthesis of organic semiconductors with pot, atom, and step economic (PASE) methods will be an
indispensable part of green electronics. In this paper, we combined direct arylation with one-pot/tandem
0
reaction to synthesize a green organic semiconductor (GOS), di(spiro[fluorene-9,9 -xanthene]-2-yl)-
1
,2,4,5-tetrafluorobenzene (DSFX-TFB), serving as the emitting layer for organic light-emitting devices
ꢀ1
ꢀ1
(OLEDs). The maximum current efficiency (CE) of 3.2 cd A , power efficiency (PE) of 2.0 lm W and
external quantum efficiency (EQE) of 4.1% were obtained with the CIE coordinates (0.15, 0.08) in the
Received 2nd September 2014
Accepted 22nd October 2014
nondoped deep-blue OLEDs. Meanwhile, good energy transfer and device performances with maximum
ꢀ1
ꢀ1
CE of 8.03 cd A and PE of 4.62 lm W were achieved in typical sky-blue fluorescent OLEDs using
DSFX-TFB as host and p-bis(p-N,N-diphenyl-aminostyryl)benzene (DSA-Ph) as dopant material. This
work provides a PASE synthetic route for GOSs and eco-friendly materials.
DOI: 10.1039/c4tc01963f
www.rsc.org/MaterialsC
and step economic (PASE) procedure developed by Clarke and
co-workers for the synthesis of tetrahydropyran-4-ones. In
1
. Introduction
9
Green electronics is a necessary part of sustainable economic general, organic semiconductors were synthesized by tradi-
and social development. In recent years, viable organic elec- tional transition metal-catalyzed cross-coupling reactions, such
tronics are on the rise due to advantages such as low cost, large- as the Suzuki and/or Stille reaction, which usually require a
5
,10
area processing and even wearable textile compared to inor- precursor with boronic acid groups and/or toxic tin groups.
ganic counterparts. Exploration of green organic semi- Recently, C–H bond activation
1
11,12
has become an alternative
conductors (GOS) in wearable electronics is also underway. synthetic technology with an atom economic and greener
1
3–16
Ideal GOSs should have four fundamental features: (1) biomass character for the design of organic semiconductors.
In
2–4
or renewable feedstocks rather than fossil raw materials; (2) addition, more concise and pot-economic synthesis methods,
5
,6
17,18
19,20
atom economic synthetic route with less hazardous reagents;
such as tandem reaction,
domino reaction,
and multi-
have been explored to synthesize
forming process; (4) nally obtained organic devices with low building blocks for sustainable organic semiconductors.
toxicity and biodegradability. Until now, there are no organic However, it is rare to make synthetic schemes of organic
21–23
(
3) low energy consumption and eco-friendly aqueous lm- component reaction
7
8
semiconductors that meet all above mentioned four features. semiconductors by combining various green and sustainable
Based on the second feature, it is one crucial challenge to methods.
design effective synthetic routes to GOSs with the pot, atom,
It is a powerful synthetic tool to combine direct arylation
with tandem reaction to synthesize GOSs since most organic pi-
semiconductors belong to arenes. In our previous work, we
a
Center for Molecular Systems and Organic Devices (CMSOD), Key Laboratory for
Organic Electronics
&
Information Displays (KLOEID), Institute of Advanced discovered a concise one-pot method for synthesizing spiro-
18
Materials (IAM), Nanjing University of Posts
&
Telecommunications, Nanjing building blocks such as spirouorenexanthene (SFX), and
2
10046, Jiangsu, China. E-mail: wei-huang@njtech.edu.cn; iamlhxie@njupt.edu.cn;
created a series of SFX-based, organic light-emitting mate-
Fax: +86 25 5813 9988; Tel: +86 25 5813 9001
24–27
rials
that have been conrmed to have excellent device
b
State Key Laboratory of Integrated Optoelectronics, College of Electronics Science and
Engineering, Jilin University, Changchun 130012, Jilin, China
performances equivalent to spirobiuorene counterparts. In
this work, we rst combined direct arylation with one-pot/
c
Jiangsu-Singapore Joint Research Center for Organic/Bio-Electronics & Information
Displays, Institute of Advanced Materials (IAM), Nanjing Tech University, Nanjing tandem reaction with PASE to synthesize a dumbbell-shaped
0
2
†
1
11816, Jiangsu, China
uorescent organic semiconductor, di(spiro[uorene-9,9 -
Electronic supplementary information (ESI) available. See DOI:
0.1039/c4tc01963f
xanthene]-2-yl)-1,2,4,5-tetrauorobenzene (DSFX-TFB), for high-
94 | J. Mater. Chem. C, 2015, 3, 94–99
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efficiency nondoped deep-blue-emitting OLEDs. In our design,
tetrauorobenzene was introduced into DSFX-TFB primarily
based on the following considerations. (1) The tetra-

uorobenzene group as an electron-withdrawing moiety bene-
ts electron injection that can balance carrier transport in the

design of bipolar organic semiconductors. Meanwhile, it can
28–30
also make spectrum blue shi and improve colour purity.
(2)
Electron-decient tetrauorobenzene facilitates the activation
of C–H bonds that make direct arylation reaction with bromi-
Fig. 1 UV-Vis and PL spectra in dilute chloroform and in thin film (a)
and cyclic voltammograms of reduction in THF solution and oxidation
in CH Cl solution (b) for DSFX-TFB.
2 2
31–33
nated SFX easy to accomplish.
It has already been incorpo-
rated into polymers and other small molecules via direct
13,14,31,33–35
arylation.
(3) SFX-capped tetrauorobenzene forms a
dumbbell-shaped molecule that is favorable for the suppression
4
01 nm in thin lm with a red shi of 26 nm (Fig. 1a), respec-
25
of intermolecular packing, which can be expected to produce
tively. Nevertheless, the PL spectrum in thin lm exhibited the
same narrow full widths at half maximum (FWHM) of 54 nm as
that in solution (Table S1†). And due to the introduction of
36–38
high device performance and better material stability.
As a
result, we used only a two-step concise and effective reaction to
synthesize the DSFX-TFB and fabricated a preliminary device

uorine atoms, the PL spectrum obviously shied blue
with a conguration of ITO/MoO (2 nm)/m-MTDATA (20 nm)/
x
0
compared with 1,4-di(spiro[uorene-9,9 -xanthen]-2-yl)benzene
NPB (10 nm)/DSFX-TFB (30 nm)/Bphen (40 nm)/LiF (1 nm)/Al.
(
DSFXB) (for synthesis and characterization, see Fig. S3†), which
exhibited the maximum emission peak at 417 nm in lm
Fig. S4†). The uorescence quantum efficiency of DSFX-TFB in
ꢀ
1
The device exhibited good current efficiency (CE, 3.2 cd A ),
ꢀ1
power efficiency (PE, 2.0 lm W ), external quantum efficiency
EQE, 4.1%), and deep-blue emission with enhanced colour
purity of CIE coordinates (0.15, 0.08). In addition, the maximum
(
(
solution is 0.81 and the value also can be as high as 0.66 in lm.
Such efficient solid-state deep-blue emission should be partially
attributed to the dumbbell-shaped conformation that effectively
suppresses molecular packing. Cyclic voltametry (CV) (Fig. 1b)
was measured to estimate its HOMO (ꢀ6.1 eV), LUMO (ꢀ2.4 eV),
and bandgap (3.7 eV). The low LUMO is consistent with other
uorinated polymers and small molecules that have been
ꢀ1
ꢀ1
CE of 8.03 cd A and PE of 4.62 lm W were obtained in the
typical host–guest OLEDs using DSFX-TFB : DSA-Ph (3 wt%) as
the emitting layer.
2. Results and discussion
29,30
widely developed and used in organic semiconductors,
The synthetic route of DSFX-TFB as green advanced material is
suggesting that the electron-injection ability of DSFX-TFB was
improved due to introduction of uorine atoms as compared
with DSFXB whose LUMO is ꢀ2.27 eV (Fig. S5†).
18
outlined in Scheme 1. As in our previous work, 2-BrSFX was
synthesized via a tandem protocol of 2-bromouorenone with
ꢁ
overdose phenol under methylsulfonic acid at 150 C. This
According to DFT calculations, DSFX-TFB exhibits cis and
trans conformations that have the same stability due to very
close frontier orbital energy levels (Fig. 2a). This probably
results in a less obvious shoulder peak at about 386 nm in the
emission spectrum of the DSFX-TFB lm, which makes the
entire spectrum look slightly wider (Fig. 1a). All the HOMOs and
LUMOs are mainly concentrated at the p-conjugated backbone
comprised of the benzene ring and uorene units in either
conformation. The charge is not localized in a specic location
even in the presence of uorine atoms, which ensures good
charge transport properties of DSFX-TFB.
greener synthesis need not be separated by column chroma-
tography with more than 75% yield. The target DSFX-TFB was
obtained through direct arylation of 2-BrSFX with 1,2,4,5-tetra-

uorobenzene using Pd(OAc)
2
as the catalyst with a yield of
1
70%. The product was conrmed by H-NMR spectroscopy and
MALDI-TOF mass spectroscopy (Fig. S1†) and found to be in
good agreement with the structure. DSFX-TFB showed high
ꢁ
decomposition temperature (440 C) and no obvious glass-
g
transition temperatures (T ) (Fig. S2†). The absorption spec-
trum of DSFX-TFB showed a main absorption band at 322 nm in
dilute chloroform solution and at 330 nm in thin lm corre-
sponding to the p / p* transition of the p-conjugated
cores (Fig. 1a). The photoluminescence (PL) emission peak of
DSFX-TFB was observed at 375 nm in chloroform solution and
Scheme 1 Synthetic procedures for the DSFX-TFB. Reaction condi-
ꢁ
tions: (a) phenol, MeSO
3
H, 150 C, 8 h, 75%. (b) 1,2,4,5-tetra- Fig. 2 HOMO and LUMO calculated using the B3LYP/6-31G basis set
ꢁ
2
fluorobenzene, Pd(OAc) , PtBu
reflux 36 h, 70%.
2
Me–HBF
4
, K
2 3
CO , DMAc, 150 C, (a) and current density versus voltage characteristics of the hole-only
and electron-only devices (b) for DSFX-TFB.
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The hole-only device with the structure of glass/ITO/MoO
x
To investigate the potential nondoped device applications of
(
(
2 nm)/NPB (30 nm)/DSFX-TFB (30 nm)/NPB (30 nm)/MoOx DSFX-TFB, a series of devices, A–E, were fabricated with multi-
2 nm)/Al (100 nm) and electron-only device with the struc- layer congurations (Fig. 3). First, we fabricated devices A–C,
ture of glass/Al (80 nm)/Cs CO (1 nm)/Bphen (40 nm)/DSFX- which have the same conguration of ITO/MoO (2 nm)/NPB
2
3
x
TFB (40 nm)/Bphen (40 nm)/Cs
2
CO
3
(1 nm)/Al (100 nm) were (30 nm)/DSFX-TFB (30 nm)/electron-transporting layer (ETL)
fabricated to investigate the charge-transport of DSFX-TFB. (40 nm)/LiF (1 nm)/Al. All the devices have the same total
The current density–voltage characteristics of these single- thickness of organic lms (100 nm). In devices A–C, DSFX-TFB
carrier devices are shown in Fig. 2b. It can be determined that served as blue light emitter, a thin-layer MoO (2 nm) and LiF (1
x
DSFX-TFB has the property of hole- and electron-transport nm) acted as anode and cathode buffer layer, and NPB as the
that facilitates the charge carrier balance. But the electron hole-injecting and transporting layer. Bphen, TPBi and Alq3
current density is higher than the hole current density, were used in the ETL to transport electrons and block hole/
indicating that DSFX-TFB exhibits better electron-transport exciton. The molecular structures of these organic compounds
ability than hole-transport capacity.
are shown in Fig. 3. The current density–voltage–luminance (J–
V–L) characteristics, efficiencies versus luminance and
Fig. 3 Structure diagram of devices A–E and chemical structures of used materials.
Fig. 4 (a) J–V–L characteristics of devices A–E. (b) Efficiency characteristics of devices A–E. (c) Normalized EL spectra of devices A–E at 6 V.
96 | J. Mater. Chem. C, 2015, 3, 94–99
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Table 1 Performance comparisons of devices A–E
a
b
b
c
c
ꢀ1
Device
V
on (V)
Emission peaks /FWHM (nm)
CIEx,y
EQE (%)
Current efficiency
Power efficiency (lm W
)
A
B
C
D
E
3.45
3.91
3.82
3.47
3.48
439/62
436/63
453/74
433/65
436/65
(0.15, 0.08)
(0.15, 0.07)
(0.16, 0.10)
(0.15, 0.08)
(0.15, 0.07)
3.5/3.4
2.2/2.1
1.1/1.1
4.1/3.9
3.7/3.6
2.7/2.7
1.7/1.6
1.0/0.9
3.2/3.1
2.9/2.8
1.7/1.2
0.8/0.6
0.5/0.3
2.0/1.3
1.9/1.3
a
b
ꢀ2
c
ꢀ2
Dened as onset voltage of log(J)–V curve. At brightness of 4000 cd m
.
Maximum values and values at 4000 cd m
.
normalized EL spectra of devices A–C are compared in Fig. 4. of m-MTDATA/NPB was 20 nm/10 nm and 10 nm/20 nm in device
The EL performances of devices A–C are summarized in Table 1. D and E, respectively. It was found that the device performance
Device A exhibited the lowest turn-on voltage of 3.45 V was improved due to the introduction of m-MTDATA in the HTL.
among the three devices and the best performance, as in This is because the m-MTDATA transition layer benets hole-
ꢀ
1
ꢀ1
maximum CE of 2.7 cd A , PE of 1.7 lm W and EQE of 3.5% transport and thus easily balances the charge carrier. Device D
(
ꢀ
1
ꢀ1
Fig. 4b and Table 1). And it obtained deep-blue emission with exhibited maximum CE of 3.2 cd A , PE of 2.0 lm W , EQE of
peak of 439 nm corresponding to CIE coordinates of (0.15, 0.08) 4.1%, and almost unchanged turn-on voltage of 3.47 V and CIE
without color shi from 4 V to 7 V (Fig. S6†) and the FWHM of coordinates of (0.15, 0.08) (Table 1). Moreover, device perfor-
62 nm. High performance probably contributed to its high PL mance can be improved when the thickness of m-MTDATA is
quantum efficiency and excellent evaporated thin-lm higher than that of NPB, compared to device E whose maximum
ꢀ1
ꢀ1
morphology. The efficiencies of device B are lower than those of CE, PE, and EQE are 2.9 cd A , 1.9 lm W , and 3.7%,
device A despite a slightly enhanced colour purity (Table 1). respectively.
39–42
When compared with device A, efficiencies drop signicantly;
moreover, at the EL emission peak, redshi appeared in device DSFX-TFB were used to fabricate the typical sky-blue uorescent
C (Fig. 4c). OLEDs with the host–guest structure as reported in the litera-
In addition, DSA-Ph as a common dopant material
and
39
As seen in the previous results, a better device performance ture. The structure of device F is ITO/MoO3 (10 nm)/NPB
was obtained using Bphen as the ETL material. Subsequently, on (40 nm)/DSFX-TFB : DSA-Ph (3 wt%, 40 nm)/Alq3 (20 nm)/LiF
the basis of device A, we have further optimized the device (0.7 nm)/Al, and the structure of device G is similar to that of
structure, which is fabricated with the conguration of device F, apart from the thickness of the emitting layer, which
ITO/MoO
x
(2 nm)/m-MTDATA (x nm)/NPB (30-x nm)/DSFX-TFB is 50 nm.
ꢀ2
(30 nm)/Bphen (40 nm)/LiF (1 nm)/Al (Fig. 3). We inserted
The maximum luminance over 20 000 cd m was obtained
m-MTDATA between MoO
x
and NPB, maintaining the thickness in both device F and device G (Fig. 5a). Nevertheless, the
of the hole-transporting layer (HTL) up to 30 nm. The thickness luminance and current density of device F were higher than
Fig. 5 (a) J–V–L characteristics of devices F and G. (b) Current efficiency and power efficiency characteristics of devices F and G. The inset
shows normalized EL spectra of devices F and G at 10 V.
Table 2 Performance of devices F and G
a
b
b
c
ꢀ1
c
ꢀ1
Device
V
on (V)
Emission peaks (nm)
CIEx,y
Current efficiency (cd A
)
Power efficiency (lm W
)
F
G
4.5
5.0
464, 492
464, 492
(0.15, 0.23)
(0.15, 0.25)
6.5/5.1/4.2
6.9/5.5/4.4
3.1/1.8/1.2
2.9/1.7/1.1
a
b
c
ꢀ2
ꢀ2
ꢀ2
Dened as onset voltage of log(J)–V curve. At 10 V. Values at 100 cd m , 1000 cd m , and 5000 cd m
.
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those of device G at the same voltage. Device F exhibited the calculated for C56
maximum CE of 8.03 cd A and PE of 4.62 lm W , which were Found: C, 82.78; H, 3.67%, F, 9.42%.
slightly higher than those of device G (Fig. 5b), but the CE was a
H
30
F
4
O
2
: C, 82.95%; H, 3.73%; F, 9.37%.
ꢀ
1
ꢀ1
little worse than that of device G when the luminance was more 3.2 Measurements
ꢀ
2
than 50 cd m . Furthermore, device F had a low turn-on voltage
of 4.5 V and a slightly better colour purity with CIE coordinates
(
The NMR spectrum was recorded on a Bruker AV 400 MHz NMR
spectrometer. Mass spectra were collected using a Microex
MALDI-TOF mass spectrometer (Bruker Daltonics, Germany).
UV-Vis absorption and photoluminescence spectra were recor-
ded with a Shimadzu UV-3600 and a Shimadzu RF-5301PC
spectrophotometer, respectively. The uorescence quantum
yields in solution and in thin lm were measured using 9,10-
diphenyl anthracene as a reference. Differential scanning
calorimetry (DSC) and thermogravimetric analyses (TGA) were
performed on a Shimadzu DSC-60A and DTG-60H Instrument,
respectively. Cyclic voltammetric (CV) studies were conducted
using a CHI600C in a typical three-electrode cell with a plat-
inum sheet working electrode, a platinum wire counter elec-
0.15, 0.23) relative to device G (Table 2). The EL spectra of
devices F and G show an intense peak at 464 nm accompanied
by a weak peak at 492 nm (Fig. 5b inset, Table 2), which is close
41
to the PL spectrum of DSA-Ph. Emissions from DSFX-TFB host,
which are at 401 nm (433–439 nm in the EL spectra, Table 1), are
not observed, indicating efficient energy transfer from the
DSFX-TFB host to the dopant.
In summary, a green organic semiconductor material
DSFX-TFB was synthesized via a relatively green tandem reac-
tion and direct arylation with PASE. Subsequently, the non-
doped deep-blue OLEDs based on DSFX-TFB with high
performance were successfully realized. The devices exhibited a
maximum EQE of 4.1% and deep-blue emission with CIE
coordinates of (0.15, 0.08). Furthermore, DSFX-TFB can be used
as a host for uorescent OLEDs with the host–guest structure
and better device performances with CE of 8.03 cd A and PE of
.62 lm W are obtained. These results proved that SFX-based
organic semiconductors that are obtained by concise and atom-
economic synthesis will be able to meet green electronics and
green chemistry requirements, as well as having potential in the
+
trode, and a silver/silver nitrate (Ag/Ag ) reference electrode.
3.3 Device fabrication
ꢀ
1
All devices were fabricated by means of vacuum deposition with
ꢀ
1
ꢀ
1
ITO glass (10 U square ) as the substrate. The ITO surface was
scrubbed and ultrasonic cleaned sequentially with detergent,
acetone, ethanol, and deionized water, and then treated in an
ultraviolet-ozone chamber aer drying in an oven. Aer the
organic layers were thermally deposited under a vacuum (about
4

eld of organic electronics. And organic semiconductors
synthesized via PASE routes will be potential advanced mate-
rials for eco-friendly devices.
ꢀ
4
ꢀ1
4
.0 ꢂ 10 Pa) at a rate of 1–2 A˚ s , 100 nm-thick Al was covered
directly on the organic layers serving as the cathode. The
2
cathode area dened an active device area of 2 ꢂ 2 mm
through a shadow mask. The current–voltage–luminance (J–V–
L) characteristics were measured with a PR-650 SpectraScan
spectrometer and a Keithley 2400 programmable voltage–
current source. All experiments and measurements were carried
out at room temperature under ambient conditions.
3
3
. Experimental section
.1 Synthesis
Synthesis of di(spiro[uorene-9,9'-xanthene]-2-yl)-1,2,4,5-
tetrauorobenzene (DSFX-TFB). A mixture of 2-bromospiro
0
3.4 Theoretical computation methods
[uorene-9,9 -xanthene] (2-BrSFX) (0.411 g, 1 mmol), 1,2,4,5-
tetrauorobenzene (0.150 g, 1 mmol), Pd(OAc) (11 mg, 0.05 Geometrical optimization for the ground and excited states was
2
t
mmol), P Bu Me–HBF P (25 mg, 0.1 mmol), K CO (0.276 g, carried out at the B3LYP/6-31G and CIS/6-31G levels, respec-
2
4
2
3
2
mmol) and N,N-dimethylacetamide (2 mL) under nitrogen tively. The TDDFT/B3LYP/6-31g calculations of the excitation
ꢁ
atmosphere was heated at 100 C for 24 h with good magnetic energies were then performed at the optimized geometries. All
stirring. Aer cooling to room temperature, the reaction the quantum-chemical calculations were performed using the
mixture was poured into saturated ethylenediaminetetraacetic- Gaussian09 suite of programs.
acid, disodium salt solution, stirred for 1 h, and then extracted
with dichloromethane. The combined organic layer was dried
Acknowledgements
over anhydrous Na SO , ltered and evaporated to dryness. The
2
4
residue was puried by silica gel column chromatography using We would like to express our sincere gratitude to the following
petroleum ether/dichloromethane mixed solvent as eluent, sources for nancial assistance: National Natural Science Fund
1
affording 0.57 g (70%) of a white solid. H NMR (400 MHz, for Excellent Young Scholars (21322402), National Natural
CDCl
3
) d 7.89 (d, J ¼ 8.0 Hz, 2H), 7.83 (d, J ¼ 7.5 Hz, 2H), 7.48 (d, Science Foundation of China (U1301243, 21373114, 21274064,
J ¼ 7.9 Hz, 2H), 7.40 (t, J ¼ 7.3 Hz, 2H), 7.27 (s, 4H), 7.24–7.16 21144004, 60876010, 61177029, 20974046, 61136003), Program
1
3
(
m, 10H), 6.79 (t, J ¼ 6.2 Hz, 4H), 6.46 (d, J ¼ 7.1 Hz, 4H).
C
for New Century Excellent Talents in University (NCET-11-0992),
NMR (100 MHz, CDCl
3
) d 155.21 (s), 155.00 (s), 151.43 (s), 140.67 Ministry of Education Doctoral Fund of China
(
(
(
s), 138.88–138.68 (m), 129.91 (s), 129.02 (s), 128.28 (s), 128.01 (20133223110007), Science and Technology Innovation Team of
s), 127.71 (s), 127.65 (s), 127.15 (s), 125.79 (s), 124.47 (s), 123.36 Jiangsu Higher Education Institutions (2013), Natural Science
s), 120.34 (s), 120.06 (s), 116.84 (s), 54.45 (s). MALDI-TOF MS: Foundation of Jiangsu Province (BK2011761, BK2008053,
calcd for C56
H
30
F
4
O
2
810.22, found 807.83 (100%). Anal. SJ209003,
BM2012010),
Priority
Academic
Program
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Journal of Materials Chemistry C
Development of Jiangsu Higher Education Institutions, PAPD 23 A. R. Siamaki, M. Sakalauskas and B. A. Arndtsen, Angew.
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