High driving voltages currently limit the commercial potential of dielectric elastomers (DEs). One method used to lower driving voltage is to increase dielectric permittivity of the elastomer. A novel silicone elastomer system with high dielectric permittivity was prepared through the synthesis of siloxane copolymers, thereby allowing for the attachment of high dielectric permittivity molecules through copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC). The synthesized copolymers allow for a high degree of chemical freedom, as several parameters can be varied during the preparation phase. Thus, the space between the functional groups can be varied, by using different dimethylsiloxane spacer units between the dipolar molecules. Furthermore, the degree of functionalization can be varied accurately by changing the feed of dipolar molecules. As a result, a completely tunable elastomer system, with respect to functionalization, is achieved. It is investigated how the different functionalization variables affect essential DE properties, including dielectric permittivity, dielectric loss, elastic modulus and dielectric breakdown strength, and the optimal degree of chemical functionalization, where these important properties are not significantly compromised, is also determined. Thus, the best overall properties were obtained for a silicone elastomer prepared with 5.6 wt% of the dipolar molecule 1-ethynyl-4-nitrobenzene. Here, a high increase in dielectric permittivity (~70%) was obtained without compromising other vital DE properties such as elastic modulus, gel fraction, dielectric and viscous loss and electrical breakdown strength.