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The Daniel K Inouye Solar Telescope (DKIST), when completed in 2019 will be the largest solar telescope built to date. DKIST will have a suite of first light polarimetric instrumentation requiring broadband polarization modulation and calibration optical elements. Compound crystalline retarders meet the design requirements for efficient modulators and achromatic calibration retarders. These retarders are the only possible large diameter optic that can survive the high flux, 5 arc minute field, and ultraviolet intense environment of a large aperture solar telescope at Gregorian focus. This dissertation presents work performed for the project. First, I measured birefringence of the candidate materials necessary to complete designs. Then, I modeled the polarization effects with three-dimensional ray-tracing codes as a function of angle of incidence and field of view. Through this analysis I learned that due to the incident converging F/13 beam on the calibration retarders, the previously assumed linear retarder model fails to account for effects above the project polarization specifications. I discuss modeling strategies such as Mueller matrix decompositions and simplifications of those strategies while still meeting fit error requirements. Finally, I present characterization techniques and how these were applied to prototype components.