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Supporting Information Toward n-type analogues to poly(3-alkylthiophene)s: Impact of side-chain variation on bulk-morphology and electron transport characteristics of head-to-tail regioregular poly(4-alkylthiazole)s
Jakob Jäger, Nadine Tchamba Yimga, Marta Urdanpilleta, Elizabeth von Hauff*, and Frank Pammer*
Figure S1. Thermogravimetric analyses a) PTzTIB, b) PTzTNB, and c) PTzTHX. Scan rate 15 ˚C/min. .......... 2
Figure S2. UV-PES ion current-curve for PTzTHX. Vertical axis: arbitrary unit. Horizontal axis: eV. ............ 2
Figure S3a/b. GIXD-refractogramms of PTzTHX and PTzTNB. ................................................................... 3
Figure S4: Architecture of the electron-only and hole-only based devices on PTzTNB/PTzTHX. ................ 4
Figure S5: Semi-logarithmic plots of J-V (left) and log (J)-log(V) (right) curves of the electron-only devices
based on PTzTHX, with the film measured as-spun, and annealed at 185°C for 10 minutes ...................... 4
Figure S6: Semi-logarithmic plots of J-V (left) and log (J)-log(V) (right) curves of the hole-only devices
based on PTzTHX, with the film measured as-spun, and annealed at 185°C for 10 minutes. ..................... 5
Figure S7: Semi-logarithmic plots of J-V (left) and log (J)-log (V) (right) curves of the electron-only and
hole-only devices based on PTzTHX, measured as-spun. .......................................................................... 5
Figure S8: Semi-logarithmic plots of J-V (left) and log (J)-log(V) (right) curves of the electron-only and
hole-only devices based on PTzTHX, with film annealed at 185°C for 10 minutes. .................................... 6
Figure S9: Semi-logarithmic plots of J-V (left) and log (J)-log(V) (right) curves of the hole-only devices
based on PTzTNB, with the film measured as-spun, and annealed at 150°C for 30 minutes. ..................... 6
Figure S10: Semi-logarithmic plots of J-V (left) and log (J)-log(V) (right) curves of the electron-only
devices based on PTzTNB, with the film measured as-spun, and annealed at 150°C for 30 minutes ......... 7
Figure S11: Semi-logarithmic plots of J-V (left) and log (J)-log (V) (right) curves of the electron-only and
hole-only based devices on PTzTNB, measured as-spun ........................................................................... 7
Figure S12: Semi-logarithmic plots of J-V (left) and log (J)-log (V) (right) curves of the electron-only and
hole-only based devices on PTzTNB, with film annealed at 150°C for 30 minutes. .................................... 8
Figure S13. 1H NMR-spectrum of 5-bromo-2-chloro-4-(triisobutylsilyloxymethyl)-thiazole (2a). ............... 9
Figure S14. 13C NMR-spectrum of 5-bromo-2-chloro-(triisobutylsilyloxymethyl)-thiazole (2a). ............... 10
Figure S15. 1H NMR-spectrum of 5-bromo-2-chloro-4-(tri(n-butyl)silyloxymethyl)-thiazole (2b). ............ 10
Figure S16. 13C NMR-spectrum of 5-bromo-2-chloro-(tri(n-butyl)silyloxymethyl)-thiazole (2b). .............. 11
Figure S17. 1H NMR-spectrum of 5-bromo-2-chloro-4-(tri(n-hexyl)silyloxymethyl)-thiazole (2c). ............ 11
Figure S18. 13C NMR-spectrum of 5-bromo-2-chloro-(tri(n-hexyl)silyloxymethyl)-thiazole (2c). .............. 12
Figure S19. 1H NMR-spectrum of PTzTIB in 1,2-dichlorobenzene-d4 at 100 oC. ....................................... 12
Figure S20.. 1H NMR-spectrum of PTzTNB in CDCl3 at 20 oC. ................................................................... 13
Figure S21. 1H NMR-spectrum of PTzTHX in CDCl3 at 20 oC. .................................................................... 13
Figure S22. 13C NMR-spectrum of PTzTHX in CDCl3. ................................................................................ 14
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.This journal is © The Royal Society of Chemistry 2016
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Figure S1. Thermogravimetric analyses a) PTzTIB , b) PTzTNB, and c) PTzTHX . Scan rate 15 ˚C/min.
Figure S2. UV-PES ion current-curve for PTzTHX . Vertical axis: arbitrary unit. Horizontal axis: eV.
a)
b)
c)
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Figure S3a. Comparison of GIXD-refractogramms of different batches of PTzTHX . The broad peak between 5 and 15° stems from the glass substrate. See also Figure S3b.
Figure S3b. Background corrected GIXD pattern of PTzTNB.
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Figure S4: Architecture of the electron-only and hole-only based devices on PTzTNB/PTzTHX.
Figure S5: Semi-logarithmic plots of J-V (left) and log (J)-log(V) (right) curves of the electron-only devices based on PTzTHX , with the film measured as-spun, and annealed at 185°C for 10 minutes
-1 0 1
-3
0
As spun
185°C
log J
(m
A/c
m2
)
Voltage(V)
Electron-only-PTzTHX
3 4 5-6
-3
0
As Spun 185°C
log
J( m
A/c
m2
)
log E(V/cm)
Electron-only-PTzTHX
5
Figure S6: Semi-logarithmic plots of J-V (left) and log (J)-log(V) (right) curves of the hole-only devices based on PTzTHX , with the film measured as-spun, and annealed at 185°C for 10 minutes.
Figure S7: Semi-logarithmic plots of J-V (left) and log (J)-log (V) (right) curves of the electron-only and hole-only devices based on PTzTHX , measured as-spun.
3 4 5
-3
-2
-1
0Hole-only-PTzTHX As Spun
185°C
log
J( m
A/c
m2)
log E(V/cm)
-1.0 -0.5 0.0 0.5 1.0
-3.0
-2.5
-2.0
-1.5
-1.0
-0.5
0.0 As Spun 185°C
log J
(m
A/c
m2)
Voltage(V)
Hole-only-PTzTHX
-1 0 1-6
-4
-2
0
Hole-only Electron-only
log J
(m
A/c
m2
)
Voltage (V)
PTzTHX-As spun
3 4 5-6
-4
-2
0PTzTHX-As spun Hole-only
Electron-only
log
J( m
A/c
m2
)
log E(V/cm)
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Figure S8: Semi-logarithmic plots of J-V (left) and log (J)-log(V) (right) curves of the electron-only and hole-only devices based on PTzTHX , with film annealed at 185°C for 10 minutes.
Figure S9: Semi-logarithmic plots of J-V (left) and log (J)-log(V) (right) curves of the hole-only devices based on PTzTNB, with the film measured as-spun, and annealed at 150°C for 30 minutes.
-1.0 -0.5 0.0 0.5 1.0
-3.0
-2.5
-2.0
-1.5
-1.0
-0.5
0.0
0.5
1.0
1.5
2.0 Hole-only
Electron-only
log J
(m
A/c
m2
)
Voltage(V)
PTzTHX-185°C
3 4 5
-3
-2
-1
0
1
2PTzTHX-185°CHole-only
Electron-only
log J
( mA
/cm
2)
log E(V/cm)
-1.0 -0.5 0.0 0.5 1.0-4.0
-3.5
-3.0
-2.5
-2.0
-1.5
-1.0
-0.5
0.0
0.5
1.0
1.5
2.0 As Spun 150°C
log
J (
mA
/cm
2)
Voltage(V)
Hole-only-PTzTNB
3 4 5-4
-3
-2
-1
0
1
2 As Spun150°C
log
J( m
A/c
m2
)
log E(V/cm)
Hole-only-PTzTNB
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Figure S10: Semi-logarithmic plots of J-V (left) and log (J)-log(V) (right) curves of the electron-only devices based on PTzTNB, with the film measured as-spun, and annealed at 150°C for 30 minutes
Figure S11: Semi-logarithmic plots of J-V (left) and log (J)-log (V) (right) curves of the electron-only and hole-only based devices on PTzTNB, measured as-spun
-1.0 -0.5 0.0 0.5 1.0
-2.5
-2.0
-1.5
-1.0
-0.5
0.0
0.5
1.0 As Spun 150°C
log J
(m
A/c
m2
)
Voltage(V)
Electron-only-PTzTNB
3 4 5
-2
-1
0
1 As Spun 150°C
log
J( m
A/c
m2
)log E(V/cm)
Electron-only-PTzTNB
-1.0 -0.5 0.0 0.5 1.0-4.0
-3.5
-3.0
-2.5
-2.0
-1.5
-1.0
-0.5
0.0
0.5
1.0 Hole-only Electron-only
log J
(m
A/c
m2
)
Voltage(V)
PTzTNB-As Spun
3 4 5-4
-3
-2
-1
0
1 Hole-only Electron-only
log J
( mA
/cm
2)
log E(V/cm)
PTzTNB-As Spun
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Figure S12: Semi-logarithmic plots of J-V (left) and log (J)-log (V) (right) curves of the electron-only and hole-only based devices on PTzTNB, with film annealed at 150°C for 30 minutes.
-1.0 -0.5 0.0 0.5 1.0
-2.5
-2.0
-1.5
-1.0
-0.5
0.0
0.5
1.0
1.5
2.0 Hole-only Electron-only
log
J (
mA
/cm
2)
Voltage(V)
PTzTNB-150°C
3 4 5-3
-2
-1
0
1
2 Hole-only Electron-only
log
J( m
A/c
m2
)
log E(V/cm)
PTzTNB-150°C
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Supplementary Analytical Data
Figure S13. 1H NMR-spectrum of 5-bromo-2-chloro-4-(triisobutylsilyloxymethyl)-thiazole (2a). For 1H NMR data of rr-PTzs recorded under similar conditions see: F. Pammer, J. Jäger, B. Rudolf, Y. Sun, Macromolecules, 2014, 47, 5904-5912.
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Figure S14. 13C NMR-spectrum of 5-bromo-2-chloro-(triisobutylsilyloxymethyl)-thiazole (2a).
Figure S15. 1H NMR-spectrum of 5-bromo-2-chloro-4-(tri(n-butyl)silyloxymethyl)-thiazole (2b).
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Figure S16. 13C NMR-spectrum of 5-bromo-2-chloro-(tri(n-butyl)silyloxymethyl)-thiazole (2b).
Figure S17. 1H NMR-spectrum of 5-bromo-2-chloro-4-(tri(n-hexyl)silyloxymethyl)-thiazole (2c).
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Figure S18. 13C NMR-spectrum of 5-bromo-2-chloro-(tri(n-hexyl)silyloxymethyl)-thiazole (2c).
Figure S19. 1H NMR-spectrum of PTzTIB in 1,2-dichlorobenzene-d4 at 100 oC.
13
Figure S20.. 1H NMR-spectrum of PTzTNB in CDCl3 at 20 oC.
Figure S21. 1H NMR-spectrum of PTzTHX in CDCl3 at 20 oC.
14
Figure S22. 13C NMR-spectrum of PTzTHX in CDCl3.
