Siloles have long been known to exhibit red-shifted fluorescence properties compared to their analogous silicon-free heterocycles due to conjugation between the Si s* orbitals and the p* orbitals of the chromophore. However, it wasn't until 2008 that this LUMO-lowering effect was shown to apply to longwavelength xanthene dyes by replacing the bridging oxygen atom with a dimethylsilyl group. Si-rhodamine dyes have been widely studied and optimized ever since, and the effect of this modification has recently been shown to extend to other classes of near-IR dye scaffolds. Despite this intense interest, and the extension of the bridge-substitution strategy to other elements, virtually all Si-dyes reported thus far have been confined to dimethyl silyl substitution. The lone counterexample among Si-rhodamines of which we are aware is the work of the Stains lab, who constructed a silanol-based sensor that undergoes oxidization to the corresponding rhodamine. Belying the nearly exclusive reliance on dimethyl silyl bridging groups amongst long-wavelength Si-dyes, a number of silyl substitutions are known within silole optical materials. The dimethyl silyl group has been ubiquitous among the Si-rhodamines reported to date presumably because of its small size and familiarity. However, more extensive modification of the silyl group -something that is not possible with oxygen bridged rhodamines -represents a missed opportunity, as it holds great promise for tuning dye behavior and tethering of Si-dyes to sensors or biomolecules. Here we show that a wide variety of silyl modifications can be productively incorporated into Si-rhodamines. Diphenyl and divinyl silyl dyes are further red-shifted by 10-15 nm compared to the standard dimethyl silyl dyes. Chloropropyl silanes include functional handles that can be used for further elaboration into iodides, clickable azides and functionalized thioethers.