Multi-fold Sonogashira coupling: a new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties. Issue 44 (1st November 2021)

• Record Type: Journal Article
• Authors: Islam, Khadimul; Narjinari, Himani; Bisarya, Akshara; Kumar, Akshai
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 44(2021)
• Page Start: 9692
• Page End: 9704
• Publication Date: 2021-11-01
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01861b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Nine new symmetric tetraalkynylated anthracenes have been synthesized via Pd(CH3 CN)2 Cl2 /cataCXium®A catalyzed tetra-fold Sonogashira coupling. Exciting photophysical properties are exhibited by these molecules in solution and in the solid-state. Abstract : For the first time, a direct single-step one-pot route to access nine new symmetric tetraalkynylated anthracenes via Pd(CH3 CN)2 Cl2 /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.