Synthesis of Dinaphtho[2,3-d:2’,3’-d’]anthra[1,2-b:5,6-b’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties
Abstract
:1. Introduction
2. Results and Discussion
2.1. Theoretical Calculations for Molecular Design
2.2. Synthesis of C6-DNADT
2.3. Physicochemical Properties of C6-DNADT
2.3.1. UV-Vis Absorption Spectrum and Cyclic Voltammogram
2.3.2. Thermal Stability
2.3.3. OFET Properties
2.3.4. AFM Images
2.3.5. GIWAXS Images
3. Materials and Methods
3.1. Instrumentation
3.2. Chemicals
3.3. Experimental Procedures
3.3.1. Synthesis of 2-Hexyl-6-methoxynaphthalene (2)
3.3.2. Synthesis of 3-Bromo-6-hexyl-2-methoxynaphthalene (3)
3.3.3. Synthesis of 3-Bromo-6-hexylnaphthalen-2-ol (4)
3.3.4. Synthesis of 3-Bromo-6-hexyl-2-(trifluoromethanesulfonyloxy)naphthalene (5)
3.3.5. Synthesis of 3-Bromo-6-hexyl-2-(2-trimethylsilylethynyl)naphthalene (6)
3.3.6. Synthesis of 6-Hexylnaphtho[2,3-b]thiophene (7)
3.3.7. Synthesis of 2,5-Bis(7-hexylnaphtho[2,3-b]thiophen-2-yl)benzendicarboxaldehyde (9)
3.3.8. Synthesis of 2,2′-(2,5-Bis(7-hexylnaphtho[2,3-b]thiophen-2-yl)-1,4-phenylene)bis(oxirane) (10)
3.3.9. Synthesis of 4,14-dihexyldinaphto[2,3-d:2′,3′-d’]anthra[1,2-b:5,6-b’]dithiophene (C6-DNADT)
3.4. Fabrication of Vapor-Deposited OFET Devices
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
OFET | Organic field-effect transistor |
C6-DNADT | 4,14-Dihexyldinaphtho[2,3-d:2’,3’-d’]anthra[1,2-b:5,6-b’]dithiophene |
GIWAXS | Grazing incidence wide-angle X-ray scattering |
AFM | Atomic force microscopy |
HOMO | Highest occupied molecular orbital |
C8-BTBT | 2,7-Dioctyl[1]benzothieno[3,2-b][1]benzothiophene |
XRD | X-ray diffraction |
DFT | Density functional theory |
NHOMO | Second (next) highest occupied molecular orbital |
DMF | N,N-Dimethylformamide |
dppf | 1,1’-Bis(diphenylphosphino)ferrocene |
THF | Tetrahydrofuran |
TMS | Trimethylsilyl |
DCE | 1,2-Dichloroethane |
NMP | N-Methyl-2-pyrrolidone |
NMR | Nuclear magnetic resonance |
UV | Ultraviolet |
TGA | Thermogravimetric analysis |
DSC | Differential scanning calorimetry |
OTS | n-Octyltrichlorosilane |
ODTS | n-Octadecyltrichlorosilane |
SAM | Self-assembled monolayer |
RMS | Root-mean-square |
TLC | Thin layer chromatography |
HRMS | High-resolution mass spectrometry |
FT-IR | Fourier transform infrared spectroscopy |
TCI | Tokyo Chemical Industry Co., Ltd. |
FAB | Fast atom bombardment |
EI | Electron impact |
equiv | Equivalent |
sat. | Saturated |
aq. | Aqueous |
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SAM | Tanneal / °C a | µmax / cm2 V–1 s–1 b | Vth/V | Ion/Ioff |
---|---|---|---|---|
OTS | as depo. | 1.9 × 10−2 | −9 | 104–105 |
50 | 2.1 × 10−2 | −13 | 104–105 | |
100 | 2.6 × 10−2 | −10 | 104–105 | |
150 | 2.1 × 10−2 | −12 | 104–105 | |
ODTS | as depo. | 1.4 × 10−2 | −22 | 104–105 |
50 | 7.7 × 10−3 | −5 | 104–105 | |
100 | 6.9 × 10−3 | −5 | 104–105 | |
150 | 4.4 × 10−3 | −2 | 104–105 |
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Ishida, T.; Sawanaka, Y.; Toyama, R.; Ji, Z.; Mori, H.; Nishihara, Y. Synthesis of Dinaphtho[2,3-d:2’,3’-d’]anthra[1,2-b:5,6-b’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties. Int. J. Mol. Sci. 2020, 21, 2447. https://doi.org/10.3390/ijms21072447
Ishida T, Sawanaka Y, Toyama R, Ji Z, Mori H, Nishihara Y. Synthesis of Dinaphtho[2,3-d:2’,3’-d’]anthra[1,2-b:5,6-b’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties. International Journal of Molecular Sciences. 2020; 21(7):2447. https://doi.org/10.3390/ijms21072447
Chicago/Turabian StyleIshida, Takumi, Yuta Sawanaka, Ryota Toyama, Zhenfei Ji, Hiroki Mori, and Yasushi Nishihara. 2020. "Synthesis of Dinaphtho[2,3-d:2’,3’-d’]anthra[1,2-b:5,6-b’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties" International Journal of Molecular Sciences 21, no. 7: 2447. https://doi.org/10.3390/ijms21072447