Journal
CCS CHEMISTRY
Volume 4, Issue 12, Pages 3798-3808Publisher
CHINESE CHEMICAL SOC
DOI: 10.31635/ccschem.022.202101625
Keywords
germanium; organic pi-conjugated molecules; ladder-type compounds; luminescence
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Funding
- National Natural Science Foundation of China [21871072]
- Program for High-Level Innovation Team in Universities of Zhejiang Province
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This study reports a simple and effective method to construct diverse germanium (Ge)-containing pi-conjugated molecules with controllable photophysical properties. Luminescent materials with specific properties were reliably predicted and designed, opening up a new avenue for organogermanium chemistry.
Considerable effort has been devoted to the design of silicon-containing pi-conjugated materials for application in optoelectronic devices and fluorescent bioimaging. However, the synthesis and spectroscopic tuning of germanium (Ge)-conjugated systems are challenging because of the paucity of synthetically useful methods. Herein, we report a simple and effective method of lithium naphthalenide-induced intramolecular cyclization to construct architecturally diverse Ge-containing pi-conjugated molecules, including benzogermoles and their ladder-type derivatives, with high yields of up to 92%. The photophysical properties of these molecules can be finely controlled by the introduction of electron-donating or -withdrawing substituents, and intense luminescence ranging from deep-blue to red regions in the solid state was observed. A quantitative model based on the Hammett constant against the luminescence wavelength showed a good linear correlation, allowing us to reliably predict and design luminescent materials with specific properties for applications. Notably, Ge-bridged ladder-type derivatives exhibited high photoluminescence and efficient deep-blue electroluminescence with good color purity. We believe this study will open a new avenue to organogermanium chemistry and offers greater flexibility for electronic structural tuning. [GRAPHICS] .
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