Date of Award


Document Type


Degree Name

Doctor of Philosophy (PhD)



First Advisor

Severin T. Schneebeli


In nature, shape defines function, and as such scientists have long since attempted to mimic nature in a pursuit to reach a similar level of fidelity. Complex macromolecular structures and shapes have been developed with interesting and unique functionalities—such as the design and synthesis of molecular machines. However, macromolecular structures such as these are difficult to synthesize. My work in the Schneebeli group builds upon this challenge, where I have developed a strategy to precisely control the shape of macromolecules to generate well-defined structures. This was accomplished with stereoisomerically pure triptycene-like derivatives as the building block pieces which have an inherent three-dimensional scaffold. With my own developed methodology by which they can be exactly functionalized, these building blocks can then couple together in a unique fashion not unlike Lego pieces. This synthetic technology leads to controlled growth of a molecular structure with precisely predictable shapes. In particular, my work involves the generation of short molecular strips, both linear and with a helical bend, as well as ladder polymer molecular helices of different pitches, which were probed for their spring-like motions. The development of these three-dimensional building blocks, their affinity for coupling in a controllable fashion, and their ability to be functionalized with through-space directed aromatic nitration methodology, laid the foundation for much of the research in the Schneebeli group related to chirality-assisted synthesis (CAS).



Number of Pages

390 p.