Date of Award


Document Type

Honors Thesis (Colby Access Only)


Colby College. Chemistry Dept.


Jeffrey L. Katz

Second Advisor

D. Whitney King


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.


oxacalixarene, anion-pi, fluoride, macrocycle, guest-host, synthesis, organic chemistry, macrocycle