In a mixing bowl, combine diced Roma tomatoes, minced garlic, chopped fresh basil, olive oil, and balsamic vinegar. Season with salt and pepper to taste, and gently stir to mix until well-coated. Allow this mixture to marinate for at least 15 minutes at room temperature.

Season the boneless, skinless chicken breasts with oregano, garlic powder, salt, and pepper to taste. Heat a skillet over medium-high heat and add a splash of olive oil. Sear the chicken for about 3-4 minutes on each side or until golden brown and cooked through. Once done, remove from heat and let rest before slicing.

Bring a large pot of salted water to a boil, then add penne pasta. Cook according to package instructions until al dente, usually about 8-10 minutes. Just before draining, reserve ¼ cup of the starchy pasta water. Drain the pasta in a colander and return it to the pot.

Return the skillet used for chicken to low heat and add the marinated bruschetta mixture. Heat gently for 1-2 minutes to warm through without cooking it down. Add the drained pasta and reserved pasta water to the skillet, tossing everything together until well coated. Top with sliced chicken and finish with grated Parmesan and extra basil.