Catalytic enrichment of oligothioalkynes: expanding horizons for functionalized oligotriazole synthesis through IrAAC-mediated post-modification

Abstract

Discrete oligomers play an important role in both advanced material development and fundamental research. Nonetheless, practical applications have been somewhat hindered by the challenges associated with their facile and diverse preparation. In this study, we introduce a rapid approach to construct a range of functionalized 1,2,3-triazole-based oligomers. This approach involves facile assembly of internal thioalkyne monomers into oligoalkynes, followed by the introduction of diverse functional groups through regiospecific iridium-catalyzed cycloaddition of azides with thioalkynes (IrAAC). We demonstrate the feasibility and efficiency of this strategy by synthesizing 27 precisely tailored functionalized oligotriazoles, derived from both “capped” and extensible oligothioalkynes. Additionally, investigation into the photophysical properties of pyrene-incorporated motifs highlights the potential of this strategy for creating functionalized oligomers, thereby impacting practical applications and enabling structure–property relationship explorations.