Title

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

Date of Award

2000

Availability

Article

Degree Name

Doctor of Philosophy (Ph.D.)

First Committee Member

Angel E. Kaifer, Committee Chair

Abstract

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.

Keywords

Chemistry, Organic

Link to Full Text

http://access.library.miami.edu/login?url=http://gateway.proquest.com/openurl?url_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&res_dat=xri:pqdiss&rft_dat=xri:pqdiss:3008202