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Heat grill to medium. Coat chicken with 1/4 cup pesto and grill 2 minutes. Flip cutlets, top with tomato and mozzarella and grill, covered, until chicken is cooked through and mozzarella has melted, 2 to 3 minutes more. Grill bread until lightly charred, 1 to 2 minutes. Brush with remaining 1/4 cup pesto and make sandwich with chicken and tomatoes.