Synthesis and Characterization of Bis-Porphyrin Receptors for Perfluoroalkyl Guests
Document Type
Thesis
Degree Name
Master of Science (MS)
Department
Chemistry
Date of Award
9-1-2026
Abstract
Per- and polyfluoroalkyl substances (PFAS) are highly stable, persistent environmental contaminants widely used in industrial and consumer products due to their resistance to heat, oil, and water; they persist in the environment due to their strong carbon-fluorine bonds which leads to resistance to degradation resulting in long-term bioaccumulation and significant health risks, including liver damage, immune dysfunction, and kidney disorders. The need to detect PFAS at ultra-low (parts-per-trillion) concentrations remains a major analytical challenge. Once detected, their removal from the environment is equally challenging. This study hypothesized that porphyrin-based receptors incorporating perfluoroalkyl functionalities could achieve enhanced sensitivity and selectivity for PFAS detection through hydrogen bonding and fluorine-fluorine interactions. To test this, a stepwise synthetic approach was employed to prepare compounds that could aid in the development of PFAS sensors and extraction agents. Bis-porphyrin-based receptors were synthesized by reacting monoamine-tetraphenylporphyrin with short-chain glutaric acid derivatives, yielding two compounds: a non-fluorinated analogue and a fluorinated receptor. These compounds were characterized using TLC, ¹H-NMR, ¹³C-NMR, ¹⁹F-NMR spectroscopy, and mass spectrometry. UV-vis binding studies indicated measurable interactions between the synthesized receptors and target guest perfluorobutanoate ion suggesting successful host-guest complex formation. These preliminary results demonstrate the feasibility of designing porphyrin-based receptors for PFAS recognition and provide a promising foundation for developing sensitive and selective detection systems to address environmental and public health challenges associated with PFAS contamination.
Advisor
Stephen Starnes
Subject Categories
Chemistry | Physical Sciences and Mathematics
Recommended Citation
Afful, Ewurabena Yebowaa, "Synthesis and Characterization of Bis-Porphyrin Receptors for Perfluoroalkyl Guests" (2026). Electronic Theses & Dissertations. 1404.
https://lair.etamu.edu/etd/1404
