Replacement of the bridging oxygen atom in xanthene dyes with a dimethylsilyl group has had a tremendous effect on biological imaging methods since its first report over 12 years ago. Yet, more extensive modification of the silyl group has thus far remained untapped. Here we have synthesized a broad range of novel Si-modified Si-rhodamine dyes that are often brighter and/or more red-shifted than the corresponding conventional dimethylsilyl dyes. Diverse functionality can be incorporated at the bridging silicon, allowing elaboration into a wealth of dyes derivatized through the Si-bridge, including molecular sensors, thiol-reactive iodides, clickable azides, aminereactive NHS esters, and dyes with specific protein-binding or DNA-targeting ligands. We demonstrate that the fluorogenic behavior of spirolactonizable Si-rhodamine dyes can be retained in Si-Bridge dyes and utilized for applications such as no-wash live cell imaging. Moreover, the ability to add sensors and targeting groups to the Si-bridge of Si-rhodamines in addition to conventional modification of the pendant phenyl opens up new possibilities in sensor design, including dual sensors, probes with both sensor and targeting groups, and different facial display of these functionalities. Modification of the bridging group as described herein is not possible with conventional oxygen-bridged xanthene dyes, but could be similarly applied to dyes with bridging elements such as carbon, germanium and phosphorus. We anticipate that Si-modification will have broad applications within Si-xanthenes and spur the development of other classes of related