Multi-fold Sonogashira coupling: a new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties?
Organic & Biomolecular Chemistry Pub Date: 2021-10-19 DOI: 10.1039/D1OB01861B
Abstract
For the first time, a direct single-step one-pot route to access nine new symmetric tetraalkynylated anthracenes via Pd(CH3CN)2Cl2/cataCXium?A catalyzed tetra-fold Sonogashira coupling is reported. Five of these tetraalkynylated anthracenes have been crystallographically characterized, with two of them exhibiting multiple interactions that significantly shorten the inter-planar distances in the solid-state structure. The rich photophysical properties exhibited by these molecules hold immense promise for future applications in sensors and optoelectronic devices. Two of the considered tetraalkynylated anthracenes comprising a D–π-A–π-D motif demonstrate solvatochromism and halochromism, with one of them showing a low bandgap of 1.79 eV. The remaining compounds demonstrate bandgaps in the range of 1.79–2.04 eV.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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