Luminescence Color Tuning from Blue to Near Infrared of Stable Luminescent Solid Materials Based on Bis-o-Carborane-Substituted Oligoacenes

Hirofumi Naito; Kenta Nishino; Yasuhiro Morisaki; Kazuo Tanaka; Yoshiki Chujo

doi:10.1002/asia.201700815

Luminescence Color Tuning from Blue to Near Infrared of Stable Luminescent Solid Materials Based on Bis-o-Carborane-Substituted Oligoacenes

Chem Asian J. 2017 Aug 17;12(16):2134-2138. doi: 10.1002/asia.201700815. Epub 2017 Jul 11.

Authors

Hirofumi Naito¹, Kenta Nishino¹, Yasuhiro Morisaki^{1

2}, Kazuo Tanaka¹, Yoshiki Chujo¹

Affiliations

¹ Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan.
² Present address: Department of Applied Chemistry for Environment, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan.

PMID: 28649772
DOI: 10.1002/asia.201700815

Abstract

Aryl-substituted o-carboranes have shown highly efficient solid-state emission in previous studies. To demonstrate color tuning of the solid-state emission in an aryl-o-carborane-based system, bis-o-carborane-substituted oligoacenes were synthesized and their properties were systematically investigated. Optical and electrochemical measurements revealed efficient decreases in energy band gaps and lowest unoccupied molecular orbital (LUMO) levels by adding a number of fused benzene rings for the extension of π-conjugation. As a consequence, bright solid-state emission was observed in the region from blue to near infrared (NIR). Furthermore, various useful features were obtained from the modified o-carboranes as an optical material. The naphthalene derivatives exhibited aggregation-induced emission (AIE) and almost 100 % quantum efficiency in the crystalline state. Furthermore, it was shown that the tetracene derivative with NIR-emissive properties had high durability toward photo-bleaching under UV irradiation.

Keywords: aggregation-induced emission; anthracene; carborane; solid-state emission; tetracene.