For the sauce: Heat a medium saucepan over medium-high heat. Add the olive oil, carrot, shallot and salt. Cook, stirring often, until softened slightly, about 2 minutes. Stir in the tomatoes, basil and Parmesan rind. Reduce the heat to medium-low and simmer for 20 minutes. Remove from the heat and stir in the mascarpone. Remove and discard the Parmesan rind. Use an immersion blender to pulse to the desired texture. Keep warm.
For the ravioli: Bring a large, shallow pot of water to a boil over high heat. Season well with salt and a drizzle of olive oil.
Combine the ricotta, mozzarella, chocolate, salt and paprika in a medium bowl. Stir together with a rubber spatula until smooth. Place a heaping teaspoon of the filling in the center of a wonton wrapper. Brush the edges with the egg wash and place another wrapper on top. Press the edges together, squeezing out any air bubbles form the center. Continue with the remaining filling and wrappers.
Add the ravioli to the boiling water in batches and cook until they float, about 2 minutes. Remove the ravioli to a plate with a slotted spoon or a spider. Serve 5 ravioli on each plate and spoon the sauce over the top. Finish with freshly grated Parmesan, as desired.