Dibenzosilines compounds have received much attention in the past decade because of their use as far red to NIR fluorophore with emission exceeding 700 nm to investigate biological processes. Generally, the common protocol to prepare dibenzosilines requires a multi-step synthetic process that goes through lithium-halogen exchange with silicon chloride to obtain the product. These synthetic routes usually require no fewer than 5-7 steps and involve harsh reaction conditions. Ir or Rh-catalyzed C–H silylation provide an opportunity to install Si by a concise approach under benign conditions. In this presentation, we will report on the synthesis of two Si-xanthene-based NIR dyes bearing phenoxazine and dihydro-phenazine wings, respectively, through two C-H silylation steps catalyzed by Ir. The introduction of Si into these two structures are not accessible by the conventional strategy. We will also discuss their applications in acoustic and fluorescence imaging in biological tissues.

Synthesis of Si-xanthene-based NIR dyes through Ir-catalyzed C-H silylation

ACS Fall 2021

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