Raman Spectroscopic Studies of Dinaphthothienothiophene (DNTT)
Abstract
:1. Introduction
2. Materials and Methods
2.1. Fabrication of Organic Field-Effect Transistor Device
2.2. Raman Measurement
2.3. Density Functional Theory Calculation
3. Results and Discussion
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
- Rogers, J.A.; Bao, Z.; Baldwin, K.; Dodabalapur, A.; Crone, B.; Raju, V.R.; Kuck, H.; Katz, H.; Amundson, K.; Ewing, J.; et al. Paper-like electronic displays: Large-area rubber- stamped plastic sheets of electronics and microencapsulated electrophoretic inks. Proc. Natl. Acad. Sci. USA 2001, 98, 4835–4840. [Google Scholar] [CrossRef] [PubMed]
- Eder, F.; Klauk, H.; Halik, M.; Zschieschang, U.; Schmid, G.; Dehm, C. Organic electronics on paper. Appl. Phys. Lett. 2004, 84, 2673–2675. [Google Scholar] [CrossRef]
- Crone, B.K.; Dodabalapur, A.; Sarpeshkar, R.; Filas, R.W.; Lin, Y.-Y.; Bao, Z.; O’Neill, J.H.; Li, W.; Katz, H.E. Design and fabrication of organic complementary circuits. J. Appl. Phys. 2001, 89, 5125–5132. [Google Scholar] [CrossRef]
- Someya, T.; Kato, Y.; Sekitani, T.; Iba, S.; Noguchi, Y.; Murase, Y.; Kawaguchi, H.; Sakurai, T. Conformable, flexible, large-area networks of pressure and thermal sensors with organic transistor active matrixes. Proc. Natl. Acad. Sci. USA 2005, 102, 12321–12325. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Katz, H.E.; Bao, Z.; Gilat, S.L. Synthetic Chemistry for Ultrapure, Processable, and High-Mobility Organic Transistor Semiconductors. Acc. Chem. Res. 2001, 34, 359–369. [Google Scholar] [CrossRef] [PubMed]
- Anthony, J.E. Functionalized Acenes and Heteroacenes for Organic Electronics. Chem. Rev. 2006, 106, 5028–5048. [Google Scholar] [CrossRef] [PubMed]
- Lin, Y.; Gundlach, D.J.; Nelson, S.F.; Jackson, T.N. Pentacene-Based Organic Thin-film Transistors. IEEE Trans. Electron Devices 1997, 44, 1325–1331. [Google Scholar] [CrossRef]
- Kelley, T.W.; Boardman, L.D.; Dunbar, T.D.; Muyres, D.V.; Pellerite, M.J.; Smith, T.P. High-Performance OTFTs Using Surface-Modified Alumina Dielectrics. J. Phys. Chem. B 2003, 107, 5877–5881. [Google Scholar] [CrossRef]
- Maliakal, A.; Raghavachari, K.; Katz, H.; Chandross, E.; Siegrist, T. Photochemical Stability of Pentacene and a Substituted Pentacene in Solution and in Thin Films. Chem. Mater. 2004, 16, 4980–4986. [Google Scholar] [CrossRef]
- Natsume, Y. Characterization of solution-processed pentacene thin film transistors. Phys. Status Solidi 2008, 205, 2958–2965. [Google Scholar] [CrossRef]
- Yamamoto, T.; Takimiya, K. Facile Synthesis of Highly π-Extended Heteroarenes, Dinaphtho[2,3-b:2′,3′-f]chalcogenopheno[3,2-b]chalcogenophenes, and Their Application to Field-Effect Transistors. J. Am. Chem. Soc. 2007, 129, 2224–2225. [Google Scholar] [CrossRef] [PubMed]
- Zschieschang, U.; Hofmockel, R.; Rödel, R.; Kraft, U.; Kang, M.J.; Takimiya, K.; Zaki, T.; Letzkus, F.; Butschke, J.; Richter, H.; et al. Megahertz operation of flexible low-voltage organic thin-film transistors. Org. Electron. 2013, 14, 1516–1520. [Google Scholar] [CrossRef]
- Yoo, S.; Yi, M.H.; Kim, Y.H.; Jang, K.-S. One-pot surface modification of poly(ethylene-alt-maleic anhydride) gate insulators for low-voltage DNTT thin-film transistors. Org. Electron. 2016, 33, 263–268. [Google Scholar] [CrossRef]
- Peng, B.; Ren, X.; Wang, Z.; Wang, X.; Roberts, R.C.; Chan, P.K.L. High performance organic transistor active-matrix driver developed on paper substrate. Sci. Rep. 2014, 4, 6430. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Kuribara, K.; Wang, H.; Uchiyama, N.; Fukuda, K.; Yokota, T.; Zschieschang, U.; Jaye, C.; Fischer, D.; Klauk, H.; Yamamoto, T.; et al. Organic transistors with high thermal stability for medical applications. Nat. Commun. 2012, 3, 723. [Google Scholar] [CrossRef] [PubMed]
- Zschieschang, U.; Ante, F.; Kälblein, D.; Yamamoto, T.; Takimiya, K.; Kuwabara, H.; Ikeda, M.; Sekitani, T.; Someya, T.; Nimoth, J.B.; et al. Dinaphtho[2,3-b:20,30-f]thieno[3,2-b]thiophene (DNTT) thin-film transistors with improved performance and stability. Org. Electron. 2011, 12, 1370–1375. [Google Scholar] [CrossRef]
- Breuer, T.; Karthäuser, A.; Klemm, H.; Genuzio, F.; Peschel, G.; Fuhrich, A.; Schmidt, T.; Witte, G. Exceptional Dewetting of Organic Semiconductor Films: The Case of Dinaphthothienothiophene (DNTT) at Dielectric Interfaces. ACS Appl. Mater. Interfaces 2017, 9, 8384–8392. [Google Scholar] [CrossRef] [PubMed]
- Chang, H.; Deng, Y.; Geng, Y.; Wang, T.; Yan, D. Effect of the initial stage of film growth on device performance of organic transistors based on dinaphtho[2,3-b:20,30-f]thieno[3,2-b]thiophene (DNTT). Org. Electron. 2015, 22, 86–91. [Google Scholar] [CrossRef]
- Basova, T.V.; Kolesov, B.A. Raman polarization studies of the orientation of molecular thin films. Thin Solid Films 1998, 325, 140–144. [Google Scholar] [CrossRef]
- Presser, V.; Schuster, B.-E.; Casu, M.B.; Heinemeyer, U.; Schreiber, F.; Nickel, K.G.; Chasse, T. Raman polarization studies of highly oriented organic thin films. J. Raman Spectrosc. 2009, 40, 2015–2022. [Google Scholar] [CrossRef]
- Stenger, I.; Frigout, A.; Tondelier, D.; Geffroy, B.; Ossikovski, R.; Bonnassieux, Y. Polarized micro-Raman spectroscopy study of pentacene thin films. Appl. Phys. Lett. 2009, 94, 133301. [Google Scholar] [CrossRef]
- Verma, P. Tip-Enhanced Raman Spectroscopy: Technique and Recent Advances. Chem. Rev. 2017, 117, 6447–6466. [Google Scholar] [CrossRef] [PubMed]
- Verma, P.; Yamada, K.; Watanabe, H.; Inouye, Y.; Kawata, S. Near-field Raman scattering investigation of tip effects on C60 molecules. Phys. Rev. B 2006, 73, 045416. [Google Scholar] [CrossRef]
- Okuno, Y.; Saito, Y.; Kawata, S.; Verma, P. Tip-enhanced Raman investigation of extremely localized semiconductor-to-metal transition of a carbon nanotube. Phys. Rev. Lett. 2013, 111, 216101. [Google Scholar] [CrossRef] [PubMed]
- Saito, Y.; Verma, P.; Masui, K.; Inouye, Y.; Kawata, S. Nano-scale analysis of graphene layers by tip-enhanced near-field Raman spectroscopy. J. Raman Spectrosc. 2009, 40, 1434–1440. [Google Scholar] [CrossRef]
- Matsui, R.; Verma, P.; Ichimura, T.; Inouye, Y.; Kawata, S. Nanoanalysis of crystalline properties of GaN thin film using tip-enhanced Raman spectroscopy. Appl. Phys. Lett. 2007, 90, 061906. [Google Scholar] [CrossRef]
- Yano, T.; Ichimura, T.; Kuwahara, S.; H’Dhili, F.; Uetsuki, K.; Okuno, Y.; Verma, P.; Kawata, S. Tip-enhanced nano-Raman analytical imaging of locally induced strain distribution in carbon nanotubes. Nat. Commun. 2013, 4, 2592. [Google Scholar] [CrossRef] [Green Version]
- Saito, Y.; Verma, P. Polarization-Controlled Raman Microscopy and Nanoscopy. J. Phys. Chem. Lett. 2012, 3, 1295–1300. [Google Scholar] [CrossRef] [Green Version]
- Mino, T.; Saito, Y.; Yoshida, H.; Kawata, S.; Verma, P. Molecular orientation analysis of organic thin films by z-polarization Raman microscope. J. Raman Spectrosc. 2012, 43, 2029–2034. [Google Scholar] [CrossRef]
- Kang, M.J.; Doi, I.; Mori, H.; Miyazaki, E.; Takimiya, K.; Ikeda, M.; Kuwabara, H. Alkylated Dinaphtho[2,3-b:2′,3′-f ]Thieno[3,2-b]Thiophenes (Cn-DNTTs): Organic Semiconductors for High- Performance Thin-Film Transistors. Adv. Mater. 2011, 23, 1222–1225. [Google Scholar] [CrossRef]
- Milvich, J.; Zaki, T.; Aghamohammadi, M.; Rödel, R.; Kraft, U.; Klauk, H.; Burghartz, J.N. Flexible low-voltage organic phototransistors based on air-stable dinaphtho[2,3-b:2’,3’-f]thieno[3,2-b]thiophene (DNTT). Org. Electron. 2015, 20, 63–68. [Google Scholar] [CrossRef]
- Becke, A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648–5652. [Google Scholar] [CrossRef]
- Lee, C.; Yang, W.; Parr, R.G. Development of the Colic-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1988, 37, 785–789. [Google Scholar] [CrossRef]
- Hosoi, Y.; Deyra, D.M.; Nakajima, K.; Furukawa, Y. Micro-Raman Spectroscopy on Pentacene Thin-Film Transistors. Mol. Cryst. Liq. Cryst. 2008, 491, 317–323. [Google Scholar] [CrossRef]
Peak | Wavenumber (cm−1) | Descriptions |
---|---|---|
1 | 1176.5 | C–H bending at the end of the aromatic rings |
2 | 1213.9 | C–H bending coupled with stretching of C(14), C(17), C(15), and C(20) atoms |
3 | 1242.5 | C–H bending; hydrogen atoms in the upper part of rings bend in-phase but hydrogen atoms in the upper and the lower parts bend anti-phase, and stretching of C(14) and C(20) atoms |
4 | 1327.8 | Deformation of thiophene rings and their adjacent aromatic rings and bending of H(26), H(28), H(35), and H(36) atoms |
5 | 1396.7 | C–C anti-symmetric stretching of aromatic rings coupled with C–H bending |
6 | 1405.8 | C–C stretching coupled with C–H bending |
7 | 1441.1 | C–C symmetric stretching of aromatic rings coupled with C–H bending |
8 | 1479.7 | C–C stretching coupled with C–H bending |
9 | 1517.0 | C–C stretching coupled with C–H bending |
10 | 1538.5 | C–C stretching of the ring with a strong stretching of C(4)–C(9) atoms and C–H bending |
11 | 1600.8 | C–C symmetric stretching of the rings coupled with C–H bending |
12 | 1635.6 | Deformation of aromatic rings |
13 | 1660.5 | Deformation of the aromatic rings except for thiophene rings |
© 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Bhardwaj, B.S.; Sugiyama, T.; Namba, N.; Umakoshi, T.; Uemura, T.; Sekitani, T.; Verma, P. Raman Spectroscopic Studies of Dinaphthothienothiophene (DNTT). Materials 2019, 12, 615. https://doi.org/10.3390/ma12040615
Bhardwaj BS, Sugiyama T, Namba N, Umakoshi T, Uemura T, Sekitani T, Verma P. Raman Spectroscopic Studies of Dinaphthothienothiophene (DNTT). Materials. 2019; 12(4):615. https://doi.org/10.3390/ma12040615
Chicago/Turabian StyleBhardwaj, Bishwajeet Singh, Takeshi Sugiyama, Naoko Namba, Takayuki Umakoshi, Takafumi Uemura, Tsuyoshi Sekitani, and Prabhat Verma. 2019. "Raman Spectroscopic Studies of Dinaphthothienothiophene (DNTT)" Materials 12, no. 4: 615. https://doi.org/10.3390/ma12040615