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Multi-fold Sonogashira coupling: a new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties

Khadimul Islam, Himani Narjinari, Akshara Bisarya, Akshai Kumar

2021Organic & Biomolecular Chemistry10 citationsDOI

Abstract

/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.

Topics & Concepts

Sonogashira couplingChemistryTetraSolid-stateMoleculeFold (higher-order function)Coupling (piping)Combinatorial chemistryPhotochemistryCatalysisPhysical chemistryMedicinal chemistryOrganic chemistryPalladiumEngineeringMechanical engineeringLuminescence and Fluorescent MaterialsRadical Photochemical ReactionsOrganoboron and organosilicon chemistry