Tetraphenylethylene substituted thienothiophene and dithienothiophene derivatives: Synthesis, optical properties and OLED applications

Article abstract of DOI:10.1039/d0tc01715a

Thieno[3,2-b]thiophene (TT) and dithieno[3,2-b;3,2-d]thiophene (DTT) have drawn immense attention in the field of electronics and optoelectronics. In this work, the first examples of TTs (TPE2-TT and TPE3-TT) and a DTT (TPE2-DTT), having tetraphenylethylene (TPE) at the periphery exhibiting aggregation induced emission (AIE) in OLEDs, were designed and synthesized by the Suzuki coupling reaction. Their properties were investigated through experimental and computational studies, as well as X-ray diffraction and DFT optimization. TPE2-TT showed excellent device performance with a maximum luminance of 11620 cd m-2, a maximum current efficiency of 6.17 cd A-1 and a maximum external quantum efficiency of 2.43%. Moreover, these synthetically easily accessible molecules have high thermal stability, which makes them perfectly suitable for optical applications. This journal is.

Full text of DOI:10.1039/d0tc01715a

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Materials for optical, magnetic and electronic devices
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Page 1 of 15
Journal of Materials Chemistry C
Tetraphenylethylene Substituted Thienothiophene and Dithienothiophene DeriVvieawtAirvticelesO;nline
DOI: 10.1039/D0TC01715A
Synthesis, Optical Properties and OLED Devices
Recep Isci,a Emine Tekin,c Kerem Kaya,a Selin Piravadili Mucur,c Sultan Funda Gorkem,b and Turan
Ozturk*, a, d
a Istanbul Technical University, Chemistry Department, Istanbul, Turkey
b Eskisehir Technical University, Faculty of Science, Department of Chemistry, Eskisehir, Turkey
c TUBITAK-MAM, Gebze, Kocaeli, Turkey
d TUBITAK UME, Chemistry Group Laboratories, Gebze, Kocaeli, Turkey
Abstract
Thieno[3,2-b]thiophene (TT) and dithieno[3,2-b;3,2-d]thiophene (DTT) have drawn an immense
attention in the field of electronics and optoelectronics. In this work, first examples of TTs (TPE2-
TT, TPE3-TT) and DTT (TPE2-DTT), having tetraphenylethylene (TPE) at the peripherals for
aggregation induced emission (AIE) applications at OLEDs, were designed and synthesized by Suzuki
coupling reaction. Their properties were investigated through experimental and computational studies,
as well as X-ray diffraction and DFT-optimization. TPE2-TT produced an excellent device
performance with a maximum luminance of 11620 cd m-2, a maximum current efficiency of 6.17 cd
A-1 and maximum external quantum efficiency of 2.43%. Moreover, these synthetically easy
accessible molecules had high thermal stability, which make them perfectly suitable for optical
applications.
Introduction
Thieno[3,2-b]thiophenes (TT) have rigid structures with an extended π-conjugation, which make them
suitable for adjusting the band gap of organic materials and increasing their intermolecular interactions
in solid state.1-5 They are electron-rich molecules, making them promising materials to construct
conjugated and low band gap organic semiconductors. Fusing one more thiophene to TT produces
dithieno[3,2-b;2,3-d]thiophene (DTT), having three thiophene units, which have also been widely used
to build promising organic materials due to their electron rich, flat and rigid delocalized systems.
Organic materials made of TTs and DTTs display interesting properties in conducting and

Journal of Materials Chemistry C
Page 2 of 15
semiconducting devices, such as organic light-emitting diodes (OLEDs), organic solar cells (OSCs)
and organic field-effect transmitters (OFETs).6-9
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DOI: 10.1039/D0TC01715A
Geometrical arrangement of organic materials in solid state has an important impact on their
fluorescence and electroluminescence properties.10-12 An important organization in solid state, called
aggregation-induced emission (AIE), pioneered by Tang et al., has been extensively studied for the
past 18 years.13 Tetraphenylethylene (TPE) is a typical moiety, having a simple structure and providing
excellent AIE property. It is known as a non-emissive chromophore in solution and highly emissive
in solid state due to its twisted structure, which causes intramolecular restriction.14-19
As a continuation of our studies on design, syntheses and properties of TTs and DTTs for
electronic and optoelectronic applications,20-24 two TTs and a DTT, possessing peripheral TPE units
to provide the materials with AIE, were synthesized. Their optoelectronic properties, along with their
applications as active layers for OLEDs, were investigated. As the TTs and DTTs developed by our
group are versatile compounds for further functionalization, we introduced TPEs at their various
peripheral positions, such as the TTs having two and three TPEs, TPE2-TT and TPE3-TT,
respectively, and a DTT, TPE2-DTT, having two peripheral TPEs. While the methoxy groups made
the main skeletons, TTs and DTT, electron richer, hindrance between phenyl and bulky TPE moieties
provided the molecules with non-planer structures; suitable for AIE studies. Thus, although several
electron-transporting, hole-blocking, solar cell and light emitting materials based on thienothiophene
(TT) and dithienothiophene (DTT) groups have been studied, to the best of our knowledge, TT, DTT
and TPE combinations for OLED application have not been reported yet.20-32
Result and Discussion
Design and Synthesis
The TTs (3, 4) and DTT 6 were synthesized according to our previously reported methods18-22 (Fig.
1). Their precursor monoketones (1, 2) were prepared in 79 and 81% yields, respectively, and the
precursor diketone 5 in 65% yield. Their ring closure reactions in refluxing chlorobenzene gave the
TTs 3 and 4 in 84 and 86% yields, respectively, and the DTT 6 in 65%. The TTs and DTT were then
brominated with NBS to obtain dibromo-TTs (7, 8) and DTT 9 (Scheme 1). Their Suzuki coupling
with TPE-borolane 10 produced the target fluorescent materials TPE2-TT (76%), TPE3-TT (73%)
and TPE2-DTT (69%).

Page 3 of 15
Journal of Materials Chemistry C
S
S
O
S
S
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DOI: 10.1039/D0TC01715A
R
R
3
4
1
2
R = OCH3
R = Br
84%
86%
TT-Ph 20
R = OCH3
R = Br
79%
81%
R = H
S
S
S
S
O
O
S
S
O
O
O
O
6
65%
5
68%
Fig. 1. Previously synthesized TTs and DTT
Scheme 1. Synthesis of TPE2-TT, TPE3-TT and TPE2-DTT
O
B
O
S
10
S
Br
NBS
S
3
Br
DMF
-10 oC
88%
S
Pd(P(Ph)3)4
K2CO3
THF
75oC
76%
O
O
7
TPE2-TT
S
S
10
S
Br
NBS
4
Br
DMF
S
Pd(P(Ph)3)4
K2CO3
THF
75oC
73%
-10 oC
Br
83%
8
TPE3-TT
10
S
S
S
S
Br
Br
NBS
DMF
6
S
Pd(P(Ph)3)4
K2CO3
THF
75oC
69%
S
-10 oC
9
O
O
O
O
80%
TPE2-DTT
Photophysical Properties
Optical properties of all the compounds were then investigated (Table 1). As expected, presence of
bulky TPEs at the peripherals of the TTs and DTT had a significant effect on their optical properties.
While the unsubstituted TT 3, TT-Ph,22 and DTT 6 displayed π−π* absorptions around 302, 300 and
293 nm, respectively, the TPE substituted TTs (TPE2-TT and TPE3-TT) and DTT (TPE2-DTT) had

Journal of Materials Chemistry C
Page 4 of 15
these absorptions with a red shift around 390, 360 and 389 nm, respectively. The band gaps were
narrowed from around 3.70 eV to between 2.80 - 2.88 eV. Most importantly, with the effect of the
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DOI: 10.1039/D0TC01715A
TPE, the non-fluorescent TTs 3, 4 and DTT 6 became fluorescent, having emission wavelengths at
500 nm (TPE2-TT), 490 nm (TPE3-TT) and 495 nm (TPE2-DTT) (Fig. 2).
Aggregation-Induced Emission Properties
AIE properties of TPE2-TT, TPE3-TT and TPE2-DTT were studied by gradual addition of distilled
water into their THF solutions (Fig. 3). Low fluorescence of TPE2-TT in THF did not change up to
addition of 50% water, after which a gradual increase was observed until 90% of water content. While
TPE2-DTT demonstrated a similar trend, a gradual increase of which was observed after addition of
20% water, TPE3-TT did not have any increase up to 90% of water, after which a dramatic increase
was observed. Possible explanations could be their packing, resulting in AIE and presence of different
number of OMe groups, since TPE2-TT with one OMe group responded to 50% of water, TPE2-
DTT with two OMe groups responded to 20% of water, and TPE3-TT with no OMe group, having
full hydrophobic character, responded to 90% of water. As all the synthesized compounds displayed
successful aggregation induced emission, their solid-state quantum yields were then measured. The
highest quantum yield was obtained with TPE3-TT (28%), the second one was TPE2-TT (21%) and
the lowest was found to be TPE2-DTT (14%). This order indicated that as the planarity was increased
a lowest quantum yield was obtained (Table 1).
Table 1. Optical Data of the Compounds.
풐풑풕풊풄
b
a
a
ϕ solid
(%)
푬
max
onset
(nm)
em
품풂풑
(nm)
(nm)
(eV)
3
302
300
293
390
360
334
329
339
430
435
443
-
3.70
3.75
3.65
2.88
2.85
2.80
-
-
TT-Ph 20
-
6
-
-
TPE2-TT
TPE3-TT
TPE2-DTT
500
490
495
21
28
14
389
b
aAbsorption and emission maxima in THF. Solid state quantum yields. Eoptic estimated from the onset of absorption
spectra.

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Journal of Materials Chemistry C
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DOI: 10.1039/D0TC01715A
Fig. 2. Absorption and emission of TPE2-TT, TPE3-TT and TPE2-DTT in THF and their
electroluminescence devices.
Fig. 3. Emission spectra as a function of the water fraction of compounds, a) TPE2-TT b) TPE3-TT
c) TPE2-DTT in THF. Luminogen concentration: 10 µM. Excited at maximum absorption
wavelengths in THF.
Single Crystal Structures
In order to have more insight on their solid state, attempts were made to grow single crystals, which
resulted in obtaining a rod-like dark yellow single crystal of TPE2-DTT with a dimension of 0.50 x
0.05 x 0.03 by slow evaporation of its chloroform solution. Crystal data and the structure refinement
parameters are given in Table S1. Table S1-S6 showed the selected bond lengths, bond and torsion a
on angles for the compound TPE2-DTT. Thermal ellipsoids and side view are plotted in Fig. 4. TPE2-
DTT was crystallized in a triclinic crystal system with P-1 space group (Fig. 4). Each unit cell
contained two molecules (Z=2).
The torsion angles between two thiophene rings and the adjacent phenyl rings of ΨS1-C18 = 34.87
and ΨS3-C450= 38.44 are suitable for π-conjugation.33 C-C average bond length of 1.481 Å between
thiophene and tetraphenylethylene units are similar to distances observed in the related literature.34

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All the bond lengths and bond and torsion angles representing dithienothiophene rings (Table S1) are
also in close agreement with the literature.35,36 The solvent molecules of water were preserved in the
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DOI: 10.1039/D0TC01715A
crystal lattice of TPE2-DTT and contained some abundant hydrogen bonding between each other.
The unit cell also contained a weak CH3-π interaction between tetraphenylethylene units of the
adjacent molecules, which is a usual behavior for molecules containing tetraphenylethylene units.37,38
It led to a relatively loose packing (Fig. 5). X-ray diffraction patterns (snapshots) collected for TPE2-
TT and TPE3-TT (Fig. S1) revealed that, contrary to the structure of TPE2-DTT, the two molecules
formed amorphous aggregates possibly due to strong π- π aggregation.
Fig. 4. X-ray crystal structures of TPE2-DTT
Fig. 5. Packing conformation of TPE2-DTT
Computational Studies
In order to have a more insight on the three molecules, density functional theory calculations were
conducted at the B3LYP/6-31 G (d, p) level. Regarding TPE2-DTT, dihedral angles between DTT
plane and TPE, DTT and methoxy substituted phenyl groups were estimated to be 38° and 49°,
respectively. Similarly, in TPE2-TT and TPE3-TT, the dihedral angle between TT plane and TPE is
40°, and TT plane and methoxy substituted phenyl units have 49°, 48°, respectively. The TPE and

Page 7 of 15
Journal of Materials Chemistry C
phenyl methoxy groups are nearly perpendicular to the DTT and TT plane in all the compounds as a
result of steric effect of the bulky TPE groups. Calculated geometry optimization data set is in
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DOI: 10.1039/D0TC01715A
agreement with the crystallographic analysis. The HOMOs were observed to be on TPE parts,
somewhat expended over TT. The calculated HOMO-LUMO gaps for TPE2-TT, TPE3-TT and
TPE2-DTT are 3.02, 3.07 and 3.02 eV, respectively. The HOMO of TPE3-TT is localized over TT
and the phenyl unit attached to the TPE3-TT, while only a minor delocalization over phenyl group
attached to TPE2-DTT was observed. Similarly, the LUMO is localized on DTT and the phenyl unit
attached DTT and the phenyl unit attached to TPE2-TT. In contrast, electrons in the HOMO and
LUMOs of TPE3-TT are localized at the same region containing, two TPE and thiophene rings. In
order to have absorption bands to obtain steady-state spectra for the compounds, N states of 50 for
singlets were computed. The λmax values of TPE2-TT, TPE3-TT and TPE2-DTT were predicted to
be 410.8, 403.7 and 410.1 nm, which shows low energy transitions resulting from HOMO-LUMO
(95.6-96%) (Fig. 6).
Fig. 6. HOMO and LUMO frontier orbitals of compounds TPE2-TT, TPE3-TT and TPE2-DTT
created at the B3LYP/6-31 G (d, p) level in gas phase, respectively from left to right.
Thermal Properties
Thermal gravimetric (TGA) analysis of the three compounds indicated two gradual endothermic
decompositions (Fig. 7). While the first decompositions of TPE3-TT and TPE2-DTT took place at
175 oC with around 10% and 50% weight loss, respectively, it was observed at 300 oC for TPE2-TT.
o
o
Second decomposition temperatures were at 450 C for TPE2-TT and TPE2-DTT, and 500 C for
TPE3-TT. Weight loss of TPE3-TT at higher temperature, compared to the other compounds,
demonstrated its better thermal stability, which is a remarkable property. The high thermal properties
are profitable to the preparation of stable and durable OLED fabrication.

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DOI: 10.1039/D0TC01715A
Fig. 7. TGA of the compounds
Electroluminescence Properties
To investigate the electroluminescence properties of the TPE2-TT, TPE3-TT and TPE2-DTT, we
fabricated OLEDs with a configuration of glass/ITO (120 nm)/NPB (60 nm)/Molecules (TPE2-TT,
TPE3-TT or TPE2-DTT) (20 nm)/TPBi (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (120 nm) (Fig. 8c). In
this configuration, ITO and LiF/Al were used as anode and cathode electrodes, respectively; (NPB)
was used as a hole injection layer; (TPBi) was used as a hole blocking layer; and tris-(8-
hydroxyquinoline) aluminum (Alq3) was used as an electron transport layer. TPE2-TT, TPE3-TT
and TPE2-DTT were used as emitting molecules (Fig. 8).
OLEDs of the three molecules TPE2-TT, TPE3-TT and TPE2-DTT were fabricated. The current
density-voltage-luminance (J-V-L) characteristics and efficiency-current density curves are depicted
in Fig. 9. Fig. 8a shows normalized EL spectra of the fabricated devices and Table 2 summarizes the
device performances. While the devices of TPE2-TT and TPE2-DTT displaced a low turn-on voltage
of 3.2 and 3.7V, respectively, the device with TPE3-TT had higher turn-on voltage of 5.0 V. Among
the three devices, TPE2-TT showed the best device performance, i.e. the highest luminance (11620
cd/m2) and the efficiency (LE: 6.17 cd/A and EQE: %2.34). According to the CIE coordinates, the
devices of TPE2-TT and TPE2-DTT had cloudy sky and TPE3-TT slightly blue emitting (Fig. 8b).
The EL spectrum of TPE2-DTT has a red shift compared to TPE2-TT and TPE3-TT, which could
be due to the extended conjugation of TPE2-DTT.

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Journal of Materials Chemistry C
Table 2: OLED performances of TPE2-TT, TPE3-TT and TPE2-DTT
Turn-on a
Voltage
EQE b
(%)
CIE
Coordinates d
L e
(cd/m2)
LE f
c
EL
View Article Online
(cd/A)
(nm)
DOI: 10.1039/D0TC01715A
(x, y)
TPE2-TT
TPE3-TT
TPE2-DTT
3.2
5.0
3.7
2.34
1.89
1.62
486
488
513
0.230, 0.456
11620
1547
2590
6.17
4.45
3.78
0.200, 0.383
0.230, 0.515
a Turn on voltage, recorded at the luminance of 1 cd m-2. b External quantum efficiency. c Maximum electro-luminescence
wavelength.d Chromaticity coordinates according to the CIE 1931 diagram. e Maximum luminance. f Luminous efficiency.
Fig. 8. a) Normalized Electro luminance Intensity- wavelength, b) device photographs and c)
schematic illustration of the device configuration of the TPE2-TT (Molecule 1), TPE3-TT (Molecule
2) and TPE2-DTT (Molecule 3).

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DOI: 10.1039/D0TC01715A
Fig. 9. d) Luminance-voltage, e) external quantum yield-current density, f) current density-voltage, g)
luminous efficiency-current density characteristics of the TPE2-TT (Molecule 1), TPE3-TT
(Molecule 2) and TPE2-DTT (Molecule 3).
Conclusion
In conclusion, three novel AIE active optic materials TPE2-TT, TPE3-TT and TPE2-DTT
containing thienothiophene (TT), dithienothiophene (DTT) and tetraphenylethylene (TPE) units were
synthesized through an easy-accessible synthetic methodology with high yields of 76, 73 and 69%,
respectively. Changes on the positions of the TPE units at the peripherals of TTs and DTT had a
dramatic effect on their optical and AIE properties. Effects of structural tuning on AIE were explained
by X-Ray analysis, computational study and device fabrication with high EQE and maximum
luminescence of 2.34% and 11620 cd/m2, respectively. The designed molecules displayed high
o
thermal stability up to around 500 C. Our work provides a new strategy to develop promising
electroluminescence materials having the closest CIE coordinates to blue emission based on TT and
DTT cores for organic material chemistry.

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Journal of Materials Chemistry C
Experimental
Materials
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All the reagents were purchased from Aldrich and Acros, used without further purifDicOaI:t1i0o.1n0.39A/Dl0lTCth01e715A
solvents used in the syntheses were technical grade and freshly distilled prior to use. The solvents used
in spectroscopic measurements were spectroscopic grade. Flash chromatography was performed with
1
≤ 0.063 µm Silica Gel. H and 13C NMR spectra were recorded on a Varian 500 and 126 MHz,
respectively, spectrometer. Proton and carbon chemical shifts are reported in parts per million
downfield from tetramethyl silane, TMS.
Synthesis
3-(4-Methoxy-phenyl)-2,5-bis-(4-triphenylvinyl-phenyl)-thieno[3,2-b]thiophene (TPE2-TT):
To the mixture of 7 (500 mg, 1.237 mmol) and 10 (1190 mg, 2.600mmol) dissolved in THF (30 mL)
and degassed for 15 minutes with N2 was added K2CO3 (5 mL, 2 M) and Pd(PPh3)4 (0.123 mmol).
o
The mixture was then saturated with N2 and the sealed reaction flask was stirred at 75 C for 48 h,
after which the
crude product was filtered through celite, extracted with sodium carbonate, dried
over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The crude
product was purified by column chromatography eluting with n-hexane: CH2Cl2 (4:1) to obtain the
title compound TPE2-TT (853 mg, 76%) as a yellow powder, mp. 115-116 o C. 1H NMR (500 MHz,
CDCl3) δ 7.43 (s, 1H), 7.38 (d, J = 8.4 Hz, 2H), 7.36 – 7.34 (m, 2H), 7.12 (m, 34H), 6.96 (d, J = 8.4
Hz, 2H), 6.90 (d, J = 8.8 Hz, 2H), 3.87 (s, 1H). 13C NMR (126 MHz, CDCl3 ) δ 158.95, 158.92, 158.87,
144.83, 143.68, 143.61, 143.58, 143.53, 143.36, 143.29, 143.05, 141.36, 140.92, 140.49, 140.30,
138.80, 137.02, 134.10, 132.76, 132.63, 131.95, 131.45, 131.43, 131.40, 131.38, 131.34, 131.33,
130.08, 128.42, 127.85, 127.76, 127.71, 127.69, 127.66, 127.60, 126.64, 126.57, 126.55, 126.50,
124.80, 115.44, 114.14, 55.24; HRMS (m/z): [M+1]+ calcd. for C66H46OS2, 907.30628; found,
907.30352.
3-(4'-Triphenylvinyl-biphenyl-4-yl)-2,5-bis-(4-triphenylvinyl-phenyl)-thieno[3,2-b]thiophene
(TPE3-TT):
To the mixture of 3 (500 mg, 1.103 mmol) and 6 (1517 mg, 3.310 mmol) dissolved in THF (30 mL)
and degassed for 10 minutes with N2 was added K2CO3 (5 mL, 2 M) and Pd(PPh3)4 (0.1103 mmol).
o
The mixture was then saturated with N2 and the sealed reaction flask was stirred at 75 C for 48 h,
after which the crude product was filtered through celite, extracted with sodium carbonate, dried over
sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The crude product
was purified by column chromatography eluting with n-hexane: CH2Cl2 (3:1) to obtain the title
1
compound TPE3-TT (973 mg, 73%) as a yellow powder, mp. 181-182 o C. H NMR (500 MHz,
CDCl3 ) δ 7.54 (d, J = 8.46 Hz, 2H), 7.43 (m, 5H), 7.37 (d, J = 8.27 Hz, 2H), 7.12 (m, 51 H), 6.95 (d,

Journal of Materials Chemistry C
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13
J = 8.43 Hz, 2H); C NMR (125 MHz, CDCl3) δ 143.752, 143.758, 143.678, 143.652, 143.625,
143.591, 143.557, 143.515, 143.331, 143.230, 143.207, 142.987, 141.421, 141.409, 141.379, 141.217,
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DOI: 10.1039/D0TC01715A
140.612, 140.512, 140.425, 140.267, 139.524, 138.204, 137.335, 137.254, 134.085, 132.555, 131.947,
131.860, 131.476, 131.430, 131.412, 131.366, 131.325, 130.002, 129.240, 129.180, 128.539, 127.837,
127.777, 127.741, 127.708, 127.679, 127.639, 127.457, 126.631, 126.558, 126.517, 126.448, 126.451,
126.020, 124.825, 115.381; HRMS (m/z): [M + 1]+ calcd. for C90H62S2, 1207.43657; found,
1207.43245.
3,5-Bis-(4-methoxy-phenyl)-2,6-bis-(4-triphenylvinyl-phenyl)-dithieno[3,2-b;2',3'-d]thiophene
(TPE2-DTT):
To the mixture of 3 (200 mg, 0.353 mmol) and 6 (340 mg, 0.741 mmol) dissolved in THF (25 mL)
and degassed for 10 minutes with N2 was added K2CO3 (2.5 mL, 2 M) and Pd(PPh3)4 (0.0353 mmol).
o
The mixture was then saturated with N2 and the sealed reaction flask was stirred at 75 C for 48 h,
after which the crude product was filtered through celite, extracted with sodium carbonate, dried over
sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The crude product
was purified by column chromatography eluting with n-hexane: CH2Cl2 (3:1) to obtain the title
compound TPE2-DTT (256 mg, 69%) as a yellow powder, dec. 236 o C. 1H NMR (500 MHz, CDCl3)
δ 7.32 (d, J = 8.7 Hz, 4H), 7.14 (m, 21H), 7.6 (m, 13H), 6.95 (d, J = 8.1 Hz, 4H), 6.87 (d, J = 8.7 Hz,
13
4H), 3.85 (s, 6H). C NMR (126 MHz, CDCl3) δ 159.01, 143.64, 143.54, 143.33, 131.45, 131.37,
131.35, 131.30, 130.12, 128.55, 128.31, 127.70, 127.67, 127.63, 127.23, 126.57, 126.54, 126.48,
114.30, 55.22; HRMS (m/z): M+ calcd. for C74H52O2S3, 1068.31239; found, 1068.31294.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
We thank Dr. Cansu Aydogan of ITU Chemistry Department for kind help for some measurements.
We thank Higher Education Council of Turkey (YOK) and TUBITAK grants to Recep Isci (PhD,
100/2000 YOK and 2211A BIDEP/TUBITAK) and Unsped Global Lojistik, Turkey, for financial
support.

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Journal of Materials Chemistry C
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DOI: 10.1039/D0TC01715A
Text and Graphic for the table of contents
Tetraphenylethylene Substituted Thieno[3,2-b]thiophene and Dithieno[3,2-b;2’,3’-
d]thiophene Derivatives; Synthesis, Optical Properties and OLED Devices
Recep Isci, Emine Tekin, Kerem Kaya, Selin Piravadili Mucur, Sultan Funda Gorkem, and
Turan Ozturk
TPE units at the peripherals of TTs and DTT affects structure, properties and OLED
fabrications of three synthetically easily accessible novel conjugated compounds for material
chemistry.