Heat 1/4 cup olive oil in a large skillet over medium heat. Add garlic; cook until fragrant, about 30 seconds. Add red pepper flakes; cook for 1 minute. Add diced tomatoes, basil, and tomato sauce; simmer, stirring occasionally, about 20 minutes.

Meanwhile, bring a large pot of lightly salted water to a boil. Cook penne until tender, about 8 minutes. Drain.

Beat eggs together in a small bowl with a fork. Place bread crumbs in a separate bowl; stir in garlic powder, salt, and black pepper. Dip 1 chicken cutlet into egg; lift up so excess egg drips back into the bowl. Press into bread crumb mixture until completely coated. Place breaded cutlet, unstacked, onto a plate. Repeat with remaining chicken cutlets.

Heat remaining 1/4 cup olive oil in a large skillet over medium heat. Add chicken cutlets; cook until dark brown, about 5 minutes per side.

Transfer cutlets to a cutting board; cut into slices. Stir chicken into sauce; simmer about 10 minutes. Add penne; simmer until soaks up flavors, 3 to 5 minutes more.