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Covalent metal-organic networks, amine coordinated complex ions, and the synthesis of novel tryptamine compounds: a thesis in Chemistry
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Covalent metal-organic networks, amine coordinated complex ions, and the synthesis of novel tryptamine compounds: a thesis in Chemistry

Duyen Kieu Pham
Master of Science (MS), University of Massachusetts Dartmouth
2022
DOI:
https://doi.org/10.62791/20236

Abstract

Covalent Metal-Organic Networks (CMONs) are a sub-class of metal organic frameworks which connect metals and linkers with strong covalent bonds. CMONs can demonstrate high thermal stability, and can include interaction sites, high surface area, and conjugated systems with extended electronic structures, giving them great potential for applications in catalysis, electronics and sensing. We have synthesized one-, two-, and three-dimensional networks of thiolate-based CMONs, using a protecting group method where pH controlled deprotection controls reaction rate and crystal formation. Our group has examined the solid-state structures of transition metal complex ions with different amines coordinated (e.g. pyridine (py), 2-picoline (2-pic), 3-picoline (3-pic), 4-picoline (4-pic), ethylenediamine (en)). We have found interesting structures, which when put in a series can be used as excellent examples of established inorganic chemistry theory. Metal-pyridine-sulfate complexes, M(py)xSO4, demonstrate a variety of structures that are textbook examples of crystal field theory. Metal-ethylenediamine-acetate complexes, [M(en)3](OAc)2, give isostructural complexes that can be used as an excellent demonstration of the Jahn-Teller distortion. Psychotropic substances have attracted a great deal of attention recently due to their potential as therapeutics to treat mental disorders including anxiety, post-traumatic stress, and addiction. Tryptamines are a broad class of hallucinogens, capable of altering sensory perception, mood and thoughts by interacting with the serotonin receptors in brain. The action and solid-state structure of many of these compounds is not well known. In our lab, many tryptamine derivatives were synthesized through alkylation, hydrolysis, neutralization reactions, etc. The products were confirmed using X-ray crystallography, and NMR. The synthesis and characterization of analytically pure tryptamines is the critical first step in studying their activity and potential use.
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