Synthesis of a Luminescent Arsolo[2,3-d:5,4-d′]bis(thiazole) Building Block and Comparison to Its Phosphole Analogue

4 years ago

Synthesis of a Luminescent Arsolo[2,3-d:5,4-d′]bis(thiazole) Building Block and Comparison to Its Phosphole Analogue

Jameel Marafie, Joshua P. Green, Martin Heeney, Andrew J. P. White, Samuel J. Cryer

The synthesis of 4-phenyl-4H-arsolo[2,3-d:5,4-d′]bis(thiazole) is reported, and its properties are compared to those of the previously prepared phosphole analogue. By comparison of their single-crystal structures, the harmonic oscillator model of heterocyclic electron delocalization (HOMHED) was used to directly compare the aromatic character of the two systems. The findings demonstrate that, although both compounds can be considered aromatic, the phosphole-containing compound had a greater degree of aromatic character than its arsole analogue. The arsole derivative exhibited excellent stability in ambient air with no formation of the arsole oxide observed upon storage. The absorption and photoluminescence spectra of the arsole derivate were subtly altered in comparison to the phosphole derivative, suggesting that changing pnictogenic atoms in such fused-ring systems to heavier analogues could be a viable way of tuning both the ambient stability and optoelectronic properties of such materials.

Publisher URL: http://dx.doi.org/10.1021/acs.organomet.7b00241

DOI: 10.1021/acs.organomet.7b00241