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Title: Enhancement of Luminescence Efficiencies by Thermal Rearrangement from ortho‐ to meta‐Carborane in Bis‐Carborane‐Substituted Acenes
Authors: Naito, Hirofumi
Uemura, Kyoya
Morisaki, Yasuhiro
Tanaka, Kazuo  kyouindb  KAKEN_id
Chujo, Yoshiki
Author's alias: 上村, 京也
田中, 一生
森崎, 泰弘
中條, 善樹
Keywords: Functional organic materials
Carboranes
Rearrangement
Luminescence
Aggregation
Acenes
Issue Date: 30-Apr-2018
Publisher: Wiley
Journal title: European Journal of Organic Chemistry
Volume: 2018
Issue: 16
Start page: 1885
End page: 1890
Abstract: In a previous study we synthesized a series of bis‐o‐carborane‐modified acenes and revealed various unique luminescence properties, such as highly efficient solid‐state emission and luminochromism. Here we report further enhancement of the luminescence efficiencies of bis‐o‐carborane‐modified acenes by thermally induced structural rearrangement from ortho‐ to meta‐carborane. We found that the thermal rearrangement of the anthracene derivative 1 occurred close to the melting point and gave luminescent products. From a detailed investigation of the product obtained from 1, the transformation of the molecular structure was proven by X‐ray crystallography. In addition, the analytical data indicated that rearrangement caused by heating at 300 °C occurred at only one of the two o‐carborane units. In accord with the results of theoretical investigations of the transition states of 1 by quantum chemical calculations, we propose that the thermal rearrangement could proceed because of a low activation energy in the first rearrangement step due to the presence of the anthracene. On the basis of optical measurements, enhancements of not only luminescence efficiencies but also aggregation‐induced emission were observed. Furthermore, we have demonstrated that this strategy for enhancing emission properties is applicable ot the corresponding tetracene derivative, resulting in a deep‐red luminescent dye.
Rights: This is the accepted version of the following article: [Hirofumi Naito, Kyoya Uemura, Kazuo Tanaka, Yasuhiro Morisaki, Yoshiki Chujo. Enhancement of Luminescence Efficiencies by Thermal Rearrangement from ortho‐ to meta‐Carborane in Bis‐Carborane‐Substituted Acenes. European Journal of Organic Chemistry, 2018, 16, 1885-1890], which has been published in final form at https://doi.org/10.1002/ejoc.201800151. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
The full-text file will be made open to the public on 25 April 2019 in accordance with publisher's 'Terms and Conditions for Self-Archiving'
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/235030
DOI(Published Version): 10.1002/ejoc.201800151
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