Date of Award
2026
Document Type
Open Access Master's Thesis
Degree Name
Master of Science in Chemistry (MS)
Administrative Home Department
Department of Chemistry
Advisor 1
Shiyue Fang
Committee Member 1
Marina Tanasova
Committee Member 2
Gordon Paterson
Abstract
This thesis describes the development of a modular synthetic route to extended conjugated aromatic systems through iterative palladium-catalyzed Sonogashira crosscoupling reactions. The work was motivated by the challenge of preparing a discrete conjugated molecule in a controlled manner. The synthetic strategy used complementary protected alkyne functionalities that could be selectively activated. This enabled sequential deprotection and coupling reactions to predictably extend the molecular scaffold. Using this approach, a series of conjugated intermediates was prepared and exponentially extended. Spectroscopic characterization by NMR and mass spectrometry supported the structures of the isolated products and the success of the iterative elongation strategy. Overall, this work establishes a synthetic foundation for the controlled construction of extended conjugated aromatic molecules and demonstrates the usefulness of modular Sonogashira cross-coupling chemistry for exponential molecular growth.
Recommended Citation
Robinson, Joden Russell, "Modular Synthesis of Conjugated Aromatic Systems via Palladium-Catalyzed Cross-Coupling Reactions", Open Access Master's Thesis, Michigan Technological University, 2026.