On-Top π-Stacking of Quasiplanar Molecules in Hole-Transporting Materials: Inducing Anisotropic Carrier Mobility in Amorphous Films†
Corresponding Author
Prof. Dr. Atsushi Wakamiya
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Precursory Research for Embryonic Science and Technology (PRESTO) (Japan) Science and Technology Agency, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012 (Japan)
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)===Search for more papers by this authorHidetaka Nishimura
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorDr. Tatsuya Fukushima
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorFuritsu Suzuki
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorDr. Akinori Saeki
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)
Search for more papers by this authorProf. Dr. Shu Seki
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)
Search for more papers by this authorDr. Itaru Osaka
Emergent Molecular Function Research Group, RIKEN CEMS, Wako, Saitama 351-0198 (Japan)
Search for more papers by this authorProf. Dr. Takahiro Sasamori
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorDr. Michihisa Murata
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Yasujiro Murata
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)===Search for more papers by this authorCorresponding Author
Prof. Dr. Hironori Kaji
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)===Search for more papers by this authorCorresponding Author
Prof. Dr. Atsushi Wakamiya
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Precursory Research for Embryonic Science and Technology (PRESTO) (Japan) Science and Technology Agency, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012 (Japan)
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)===Search for more papers by this authorHidetaka Nishimura
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorDr. Tatsuya Fukushima
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorFuritsu Suzuki
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorDr. Akinori Saeki
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)
Search for more papers by this authorProf. Dr. Shu Seki
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871 (Japan)
Search for more papers by this authorDr. Itaru Osaka
Emergent Molecular Function Research Group, RIKEN CEMS, Wako, Saitama 351-0198 (Japan)
Search for more papers by this authorProf. Dr. Takahiro Sasamori
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorDr. Michihisa Murata
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Yasujiro Murata
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)===Search for more papers by this authorCorresponding Author
Prof. Dr. Hironori Kaji
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011 (Japan)===Search for more papers by this authorThis work was partially supported by JST and the Collaborative Research Program at the ICR, Kyoto Univ. Support was also received from the Funding Program for World Leading Innovative R&D on Science and Technology (FIRST Program). The NMR measurements were supported by the Joint Usage/Research Center (JURC) at the ICR, Kyoto Univ. Synchrotron single-crystal X-ray analysis was carried out with the SPring-8 beam line BL38B1 with the approval of JASRI (2012A1448, 2012B1319, and 2013A1489). 2D GIXD experiments were performed at BL19B2 of SPring-8 with the approval of JASRI (2013A1634). We thank Dr. T. Koganezawa (JASRI) for advice on the 2D GIXD measurements.
Abstract
Dimers of partially oxygen-bridged triarylamines were designed and synthesized as hole-transporting materials. X-ray structural analyses revealed that these compounds form on-top π-stacking aggregates in the crystalline state. TRMC measurements showed that high levels of anisotropic charge transport were induced in the direction of the π-stacking. Surprisingly, even in vacuum-deposited amorphous films, these compounds retained some of the face-on π-stacking, thus facilitating an out-of-plane carrier mobility.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| ange_201400068_sm_miscellaneous_information.pdf9.6 MB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aY. Shirota, H. Kageyama, Chem. Rev. 2007, 107, 953–1010;
- 1bL. Xiao, Z. Chen, B. Qu, J. Luo, S. Kong, Q. Gong, J. Kido, Adv. Mater. 2011, 23, 926–952.
- 2
- 2aJ. E. Anthony, Angew. Chem. 2008, 120, 460–492;
10.1002/ange.200604045 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 452–483;
- 2bH. Klauk, Chem. Soc. Rev. 2010, 39, 2643–2666;
- 2cC. Wang, H. Dong, W. Hu, Y. Liu, D. Zhu, Chem. Rev. 2012, 112, 2208–2267.
- 3
- 3aB. Walker, C. Kim, T.-Q. Nguyen, Chem. Mater. 2011, 23, 470–482;
- 3bA. Facchetti, Chem. Mater. 2011, 23, 733–758;
- 3cA. Mishra, P. Bäuerle, Angew. Chem. 2012, 124, 2060–2109; Angew. Chem. Int. Ed. 2012, 51, 2020–2067;
- 3dR. S. Kularatne, H. D. Magurudeniya, P. Sista, M. C. Biewer, M. C. Stefan, J. Polym. Sci. Part A 2013, 51, 743–768;
- 3eI. Osaka, T. Kakara, N. Takemura, T. Koganezawa, K. Takimiya, J. Am. Chem. Soc. 2013, 135, 8834–8837.
- 4V. Coropceanu, J. Cornil, D. A. S. Filho, Y. Olivier, R. Silbey, J.-L. Brédas, Chem. Rev. 2007, 107, 926–952.
- 5D. Holmes, S. Kumaraswamy, A. J. Matzger, K. P. C. Vollhardt, Chem. Eur. J. 1999, 5, 3399–3412.
10.1002/(SICI)1521-3765(19991105)5:11<3399::AID-CHEM3399>3.0.CO;2-V CAS Web of Science® Google Scholar
- 6
- 6aJ. E. Anthony, J. S. Brooks, D. L. Eaton, S. R. Parkin, J. Am. Chem. Soc. 2001, 123, 9482–9483;
- 6bX. Zhang, A. P. Coté, A. J. Matzger, J. Am. Chem. Soc. 2005, 127, 10502–10503;
- 6cQ. Miao, X. Chi, S. Xiao, R. Zeis, M. Lefenfeld, T. Siegrist, M. L. Steigerwald, C. Nuckolls, J. Am. Chem. Soc. 2006, 128, 1340–1345.
- 7aN,N′-Diphenyl-N,N′-di(m-tolyl)benzidine: Z. Zhang, Z. E. Burkholder, J. Zubieta, Acta Crystallogr. Sect. C 2004, 60, o 452–o454;
- 7b4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl: L.-Q. Huang, Q.-Y. Cao, C. Yi, C.-J. Yang, X.-C. Gao, Acta Crystallogr. Sect. E 2006, 62, o 2075–o2076.
10.1107/S1600536806029527 Google Scholar
- 8T. Yamada, T. Sato, K. Tanaka, H. Kaji, Org. Electron. 2010, 11, 255–265.
- 9M. Kuratsu, M. Kozaki, K. Okada, Chem. Lett. 2004, 33, 1174–1175.
- 10J. Pommerehne, H. Vestweber, W. Guss, R. F. Mahrt, H. Bässler, M. Porsch, J. Daub, Adv. Mater. 1995, 7, 551–554.
- 11
- 11aA. Saeki, Y. Koizumi, T. Aida, S. Seki, Acc. Chem. Res. 2012, 45, 1193–1202, and references therein;
- 11bA. Saeki, S. Seki, T. Takenobu, Y. Iwasa, S. Tagawa, Adv. Mater. 2008, 20, 920–923;
- 11cY. Yasutani, A. Saeki, T. Fukumatsu, Y. Koizumi, S. Seki, Chem. Lett. 2013, 42, 19–21.
- 12The charge carrier generation efficiency (ϕ=1.76×10−4 for 2) was measured for the vacuum-deposited film and was subsequently used to estimate the local mobility Σμ in the crystals.
- 13
- 13aD. Yokoyama, J. Mater. Chem. 2011, 21, 19187–19202, and references therein;
- 13bD. Yokoyama, A. Sakaguchi, M. Suzuki, C. Adachi, Appl. Phys. Lett. 2008, 93, 173302.
- 14
- 14aA. Kojima, K. Teshima, Y. Shirai, T. Miyasaka, J. Am. Chem. Soc. 2009, 131, 6050–6051;
- 14bM. M. Lee, J. Teuscher, T. Miyasaka, T. N. Murakami, H. J. Snaith, Science 2012, 338, 643–647;
- 14cJ. H. Heo, S. H. Im, J. H. Noh, T. N. Mandal, C.-S. Lim, J. A. Chang, Y. H. Lee, H. Kim, A. Sarkar, M. K. Nazeeruddin, M. Grätzel, S. I. Seok, Nat. Photonics 2013, 7, 486–491.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.
