On-top π-stacking of quasiplanar molecules in hole-transporting materials: inducing anisotropic carrier mobility in amorphous films

Atsushi Wakamiya; Hidetaka Nishimura; Tatsuya Fukushima; Furitsu Suzuki; Akinori Saeki; Shu Seki; Itaru Osaka; Takahiro Sasamori; Michihisa Murata; Yasujiro Murata; Hironori Kaji

doi:10.1002/anie.201400068

On-top π-stacking of quasiplanar molecules in hole-transporting materials: inducing anisotropic carrier mobility in amorphous films

Angew Chem Int Ed Engl. 2014 Jun 2;53(23):5800-4. doi: 10.1002/anie.201400068. Epub 2014 Apr 24.

Authors

Atsushi Wakamiya¹, Hidetaka Nishimura, Tatsuya Fukushima, Furitsu Suzuki, Akinori Saeki, Shu Seki, Itaru Osaka, Takahiro Sasamori, Michihisa Murata, Yasujiro Murata, Hironori Kaji

Affiliation

¹ 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). wakamiya@scl.kyoto-u.ac.jp.

PMID: 24764307
DOI: 10.1002/anie.201400068

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.

Keywords: amorphous materials; heterocycles; semiconductors; structure elucidation; structure-function relationships.