Part I: Rapid Synthesis of Dendrimers by an Orthogonal Coupling Strategy. Part II: Design, Synthesis, and Characterization of Hydrogen-Bond Mediated Self-Assembling Dendrimers

Part I. Layered dendrimers were rapidly synthesized using an orthogonal coupling strategy. Fourth generation dendron 71 was prepared in four steps by sequential use of two AB$\sb2$ building blocks 66 and 67 under Mitsunobu esterification and Sonogashira coupling conditions. Further accelerated growth was achieved by merging the orthogonal coupling strategy with Frechet's branched-monomer approach. Thus, sixth generation dendron 81, with molecular formula $\rm C\sb{1292}H\sb{1369}IO\sb{242}$ and a molecular weight of 20897 amu, was synthesized in just three steps from the corresponding AB$\sb4$ monomers 72 and 73. In comparison to the most efficient dendrimer synthesis available, the orthogonal coupling strategy halves the number of synthetic steps needed by obviating protection-deprotection and activation chemistry.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2015

Author dc:creator

• Zeng, Fanwen

Contributors dc:contributor

• Zimmerman, Steven C.

• Chemistry, Organic
• Chemistry, Polymer

Language dc:language

eng

Identifier

(UMI)AAI9737300

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/77259