Design amphiphilic dipolar π-systems for stimuli-responsive luminescent materials using metastable states

Shiki Yagai (), Satoru Okamura, Yujiro Nakano, Mitsuaki Yamauchi, Keiki Kishikawa, Takashi Karatsu, Akihide Kitamura, Akira Ueno, Daiki Kuzuhara, Hiroko Yamada, Tomohiro Seki and Hajime Ito
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Shiki Yagai: Graduate School of Engineering, Chiba University
Satoru Okamura: Graduate School of Engineering, Chiba University
Yujiro Nakano: Graduate School of Engineering, Chiba University
Mitsuaki Yamauchi: Graduate School of Engineering, Chiba University
Keiki Kishikawa: Graduate School of Engineering, Chiba University
Takashi Karatsu: Graduate School of Engineering, Chiba University
Akihide Kitamura: Graduate School of Engineering, Chiba University
Akira Ueno: Microjet Corporation
Daiki Kuzuhara: Graduate School of Material Science, Nara Institute of Science and Technology (NAIST)
Hiroko Yamada: Japan Science and Technology Agency (JST), Core Research for Evolutional Science and Technology (CREST)
Tomohiro Seki: Graduate School of Engineering, Hokkaido University
Hajime Ito: Graduate School of Engineering, Hokkaido University

Nature Communications, 2014, vol. 5, issue 1, 1-10

Abstract: Abstract π-Conjugated compounds that exhibit tunable luminescence in the solid state under external mechanical stimuli have potential applications in sensors and imaging devices. However, no rational designs have been proposed that impart these mechano-responsive luminescent properties to π-conjugated compounds. Here we demonstrate a strategy for mechano-responsive luminescent materials by imparting amphiphilic and dipolar characteristics to a luminescent π-conjugated system. The oligo(p-phenylenevinylene) luminophore with a didodecylamino group at one end and a tri(ethylene glycol) ester group at the other end yields segregated solid structures by separately aggregating its hydrophobic and hydrophilic moieties. The segregated structures force the molecules to align in the same direction, thereby generating a conflict between the side-chain aggregation and dipolar stabilization of the π-system. Consequently, these metastable solid structures can be transformed through mechanical stimulation to a more stable structure, from a π–π stacked aggregate to a liquid crystal and further to a crystalline phase with variable luminescence.

Date: 2014
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DOI: 10.1038/ncomms5013

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