Date of Award
2019
Document Type
Honors Thesis (Colby Access Only)
Department
Colby College. Chemistry Dept.
Advisor(s)
Jeffrey L. Katz
Second Advisor
D. Whitney King
Abstract
Because of their relative absence from chemical literature, oxacalix[4]arenes have been a main focus of work done in the Katz Lab. This project focuses on the synthesis of novel oxacalix[2]arene[2]naphthalimides via nucleophilic aromatic substitution (SNAr). The 1,3- alternate conformation of these molecules makes them excellent candidates for guest-host complexation studies, and the electron-deficient naphthalimides included in this work are specifically being considered for anion-pi interactions. Specifically, these molecules are tested as colorimetric sensors of fluoride in solution as measured through absorbance. Through curve fitting of these spectra, it was determined that at least one of these macrocycles shows formation of what is likely an anion-pi interaction as calculated from binding constants and binding energies. Other species have shown responses to fluoride that require more complicated analyses as they form multiple complexes.
Keywords
oxacalixarene, anion-pi, fluoride, macrocycle, guest-host, synthesis, organic chemistry, macrocycle
Recommended Citation
Forzano, Joseph A., "Synthesis of Oxacalix[2]arene[2]naphthalimides and Exploration of Anion-Pi Interactions for Colorimetric Fluoride Sensing" (2019). Honors Theses. Paper 934.https://digitalcommons.colby.edu/honorstheses/934