Document Type
Thesis - University Access Only
Award Date
2002
Degree Name
Doctor of Philosophy (PhD)
Department / School
Chemistry
Abstract
In pursuit of novel dendrimers, stable isocyanate-based dendritic building blocks were synthesized under mild conditions (15 min. at room temperature) by the DMAPcatalyzed reaction of simple amine buildingblocks with di-tert-butyldicarbonate in high yield. We attached isocyanate-based dendritic building blocks to 3-aminopropylfunctionalized silica gel. These compoupds can potentially mimic immobilized micelles. A convergent synthesis of I 3 C-branched polyamide dendrons was developed providing a facile access to defined monodispersive dendritic building blocks. These polyamide dendrons are of interest to chemists due to their high branching multiplicity and bulkiness as well as the hydrophilicity of their corresponding polyacids. Changing 2nd polyamide dendrons into isocyante-based dendritic building blocks was accomplished using di-tert-butyldicarbonate and DMAP in high yield. In addition, modification of P AMAM dendrimers was performed using isocyanate dendritic -building blocks to generate new dendrimers. Photodendrimers are dendrimers that contain functional groups that undergo cis/trans isomerization in the presence of light at a specific wavelength. Although these compounds have studied since 1993, the photoactive functional group for the known target molecules has been the azobenzene group. The N,N-dimethyl-p-methoxycinnamides are also photoacti\·e with well characterized isomerization wavelengths. Synthesis of the N,N-dimethyl-p-hydroxycinnamides will be discussed including the development of a new synthetic pathway to these compounds and synthesis of a series of potentially photoactive dendrimers. In order to obtain an immunogenic response, the compound of interest (a hapten) must have a sufficiently large molecular weight. Many different proteins have been used as carriers for haptens. Unfortunately, proteins often illicit undesired toxic responses. Studies using poly-L-aspartic acid and poly-L-glutamic acid indicate that the linear polyL-aspartic acid results in lo\\. toxicity. As part of our research, we would like to develop a L-aspartic acid based dendrimer and determine its effectiveness as a hapten carrier. Attempts to design and synthesize an artificial protein carrier have been investigated. A second generation dendrimer based on L-aspartic acid was synthesized in modest yield using standard solution peptide synthetic methods.
Library of Congress Subject Headings
Dendrimers -- Synthesis Macromolecules
Format
application/pdf
Number of Pages
163
Publisher
South Dakota State University
Recommended Citation
Lu, Genliang, "Synthesis of Isocyanate-based Dendrimers, Photodendrimers and L-aspartic Acid Based Dendrimers" (2002). Electronic Theses and Dissertations. 929.
https://openprairie.sdstate.edu/etd2/929