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Home  >  Journal list  >  Polymer Journal  >  Vol.49  No.1 (2017)  >  pp.215-221

Polymer Journal
<<Previous article Vol.49  No.1 (2017)   pp.215 - 221 Next article>>

Alkylated oxygen-bridged V-shaped molecules: impacts of the substitution position and length of the alkyl chains on the crystal structures and fundamental properties in aggregated forms

Chikahiko Mitsui1,2, Tatsuro Annaka1, Ken-ichi Nakamura1, Masato Mitani1,2, Daisuke Hashizume2, Katsumasa Nakahara1, Masakazu Yamagishi1, Takanari Ueno3, Yuji Tanaka3, Masafumi Yano3, Daichi Iwasawa4, Miki Hasegawa4, Hiroyasu Sato5, Akihito Yamano5, Jun Takeya1 and Toshihiro Okamoto1,2,6
1Department of Advanced Materials Science, Graduate School of Frontier Sciences, The University of Tokyo, Chiba, Japan
2Materials Characterization Support Unit, Center for Emergent Matter Science (CEMS), Saitama, Japan
3Chemistry, Materials and Bioengineering Major, Graduate School of Science and Engineering, Kansai University, Osaka, Japan
4Department of Chemistry and Biological Science, College of Science and Engineering, Aoyama Gakuin University, Kanagawa, Japan
5Rigaku Corporation, Tokyo, Japan
6PRESTO, Japan Science and Technology Agency (JST), Saitama, Japan

We have recently developed dinaphtho[2,3-b:2',3'-d]furan (DNF–V) derivatives as a new type of solution-processable organic semiconducting material with high carrier mobility and high emission efficiency in the solid state. In this article, we systematically investigate and reveal the impact of the substitution position and the length of the alkyl side chains on their physicochemical properties based on their packing structures. For both alkylated DNF–VV and DNF–VW derivatives, the solubilities and the phase-transition temperatures increase as the shorter alkyl chains are attached. In particular, alkylated DNF–VV simultaneously achieve high solubility (over 1wt%) and a highly stabilized crystal phase (up to 199°C). Furthermore, DNF–V derivatives exhibit a deep-blue emission in the solid state with a quantum efficiency ranging from 17 to 51%. Such a range of physicochemical properties is probably related to the dependencies on the molecular geometry in the crystal state and the length of the alkyl side chains.

Received: June 30, 2016 , Revised: September 18, 2016
Accepted: September 20, 2016 , Published online: November 09, 2016
© 2017 The Society of Polymer Science, Japan

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