Preparation of [n]cavitands and bipyridinium functionalized electrochemically active cavitands

Date of Award




Degree Name

Doctor of Philosophy (Ph.D.)

First Committee Member

Angel E. Kaifer - Committee Chair


In this dissertation, the author describes the synthesis and characterization of a new family of cavitands, [n]cavitands, composed of 4--7 resorcinol units as well as the synthesis and characterization of a novel class of bipyridinium-functionalized cavitand. These novel compounds were characterized by varied techniques, such as 1H and 13C NMR spectroscopy, X-ray diffraction, mass spectrometry and elemental analysis.Chapter one briefly reviews the existing chemical literature related to cavitands.Chapter two describes the synthesis of [n]cavitands. The results indicate that the low-order cavitands exist in the previously observed cone-like conformation whereas the high-order cavitands manifest lower symmetry and show flexibility at room temperature, with interconversion between equivalent conformations.Chapter three describes the synthesis and characterization of bipyridinium-functionalized cavitands. Some of these compounds have a molecular weight higher than 4000 daltons and they can be considered as dendrimers with cavitand core.Chapter four shows the electrochemical studies performed on bipyridinium-based cavitands. The presence of bipyridinium units confers redox properties to these compounds. Their electrochemical behavior was studied by cyclic voltammetry in acetonitrile solutions.


Chemistry, Organic

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