Initial synthesis of new Si-Bridge rhodamines. To allow rapid access to novel Si-substituted dyes, we began with dibromo scaffold 1 (Scheme 1). Lithium-halogen exchange chemistry followed by reaction with different commercially available and synthesized dichlorosilanes afforded Si-leuco dyes, which were directly oxidized with p-chloranil to yield the desired Sirhodamines 4-17, purified as the TFA salt (Scheme 1). Gratifyingly, most dichlorosilanes yielded the expected Si-rhodamine dyes, with the exception of cyclobutyl and cyclopentyl dichlorosilanes, which form strained and likely unstable reaction products. Asymmetrically substituted Si-dyes led to two isomers that were evident by NMR but not separated by chromatography.