The use of combinatorial and high-throughput approaches in the design and exploration of materials space has been gaining increasing acceptance in recent years. While these methods have been successfully employed in the development of materials for the fields of electronics and optics, only a few examples exist within the field of biomaterials science. While there is a clear need for complex polymer structures that can be tailored for specific applications, most current research is being done on the basis of “trial and error” approaches that simply cannot keep up with the demand for novel technologies.

As part of the work involved in this thesis, the number of viable biomaterial candidates was increased by varying the chemical composition of tyrosine-derived monomers in two positions, namely the backbone and pendent chain. The resulting monomers proved to have different physical and chemical properties, derived from small modifications to their chemical structure.

In order to effectively synthesize several compositions of tailored tyrosine-derived polycarbonates, automated synthetic procedures were created and evaluated in a modern robotic platform. The challenges involved in the automation of polycondensation reactions, such as liquid handling, dropwise addition, and toxic chemical handling, were addressed successfully. A considerable amount of time was saved in comparison to manual methods when generating large polymer libraries.

In order to study structure-property relationships, the mass-per-flexible-bond principle was used to quantitatively explain the large range of glass transitions observed in a library of polymers containing homo-, co-, and terpolymers. Within this context, the information gathered in this thesis is expected to be used as a guideline for the rational design of polymers for specific applications.

The information derived from this work made it possible to ascertain that future research can certainly benefit from the automated parallel synthesis methods developed during it, as well as from the linear relationships found. It is expected for the research done in this thesis to have a definite impact not only on the use of combinatorial and high-throughput approaches in polymer science, but also on the informatics aspect involved.