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Porphyrins present one of the most ubiquitous classes of compounds in chemistry, optics, medicine, and materials science. This is a result of their multifaceted roles in nature and the wide range of tunable molecular properties. Further advances in translational research and a more detailed understanding of their biological function require a specific tailoring of the macrocycle to the desired task. Using examples from our own research we illustrate how a targeted molecular design combining the aspects of conformational flexibility with rational chemical synthesis in porphyrins can be used to advance our knowledge of cofactor function and to develop novel and highly efficient materials.