5 years ago

Arene-Inserted Extended Germa[n]pericyclynes: Synthesis, Structure, and Phosphorescence Properties

Arene-Inserted Extended Germa[n]pericyclynes: Synthesis, Structure, and Phosphorescence Properties
Shunichiro Ito, Kazuo Tanaka, Yasuhiro Nishiyama, Junta Mori, Kiyomi Kakiuchi, Tsumoru Morimoto, Yoshiki Chujo, Hiroki Tanimoto
This report describes the synthesis and characterization of arene-inserted extended (ArEx) germa[n]pericyclynes composed of germanium and 1,4-diethynylbenzene units. These novel cyclic germanium-π unit materials were synthesized with diethynylbenzene and germanium dichloride. X-ray crystallographic analysis revealed their structures, and the planar conformation of ArEx germa[4]pericyclyne along with the regular aromatic rings. UV/Vis absorption spectra and fluorescence emission spectra showed considerably unique and highly improved character compared to previously reported germa[n]pericyclynes. Even in the absence of transition metal components, phosphorescence emissions were observed, and the emission lifetimes were dramatically improved. ArEx germa[n]pericyclynes showed high photoluminescence quantum yields, whereas low photoluminescence quantum yields were observed for acyclic compounds. Density functional theory calculations show delocalized orbitals between skipped alkyne units through a germanium tether, and an increase in the HOMO energy level, leading to a small HOMO–LUMO energy gap. A link to the future: This report describes the syntheses of arene-inserted type extended (ArEx) germa[n]pericyclynes composed of germanium-1,4-diethynylbenzene units, and their characterization. These novel cyclic germanium-π unit materials were characterized by X-ray crystallography, UV/Vis spectroscopy, fluorescence, and phosphorescence emission spectroscopy, which showed characteristic optical properties and large emission lifetimes compared to previous derivatives.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701359

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