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Sci Rep. 2018 Sep 27;8(1):14448. doi: 10.1038/s41598-018-32486-z.

Thienoisoindigo-Based Semiconductor Nanowires Assembled with 2-Bromobenzaldehyde via Both Halogen and Chalcogen Bonding.

Author information

1
School of Chemical Engineering and Materials Science, Institute of Energy Converting Soft Materials, Chung-Ang University (CAU), Seoul, 06974, Republic of Korea.
2
Department of Energy Engineering, School of Energy and Chemical Engineering, Perovtronics Research Center, Low Dimensional Carbon Materials Center, Ulsan National Institute of Science and Technology (UNIST), Ulsan, 44919, Republic of Korea.
3
Advanced Nano-Surface Research Group, Korea Basic Science Institute (KBSI), Daejeon, 34133, Republic of Korea.
4
Department of Molecular Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan.
5
UNIST Central Research Facilities & School of Natural Science, Ulsan National Institute of Science and Technology (UNIST), Ulsan, 44919, Republic of Korea.
6
Department of Energy Engineering, School of Energy and Chemical Engineering, Perovtronics Research Center, Low Dimensional Carbon Materials Center, Ulsan National Institute of Science and Technology (UNIST), Ulsan, 44919, Republic of Korea. yang@unist.ac.kr.
7
School of Chemical Engineering and Materials Science, Institute of Energy Converting Soft Materials, Chung-Ang University (CAU), Seoul, 06974, Republic of Korea. jpark@cau.ac.kr.

Abstract

We fabricated nanowires of a conjugated oligomer and applied them to organic field-effect transistors (OFETs). The supramolecular assemblies of a thienoisoindigo-based small molecular organic semiconductor (TIIG-Bz) were prepared by co-precipitation with 2-bromobenzaldehyde (2-BBA) via a combination of halogen bonding (XB) between the bromide in 2-BBA and electron-donor groups in TIIG-Bz, and chalcogen bonding (CB) between the aldehyde in 2-BBA and sulfur in TIIG-Bz. It was found that 2-BBA could be incorporated into the conjugated planes of TIIG-Bz via XB and CB pairs, thereby increasing the π - π stacking area between the conjugated planes. As a result, the driving force for one-dimensional growth of the supramolecular assemblies via π - π stacking was significantly enhanced. TIIG-Bz/2-BBA nanowires were used to fabricate OFETs, showing significantly enhanced charge transfer mobility compared to OFETs based on pure TIIG-Bz thin films and nanowires, which demonstrates the benefit of nanowire fabrication using 2-BBA.

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