Date of Award

Spring 5-7-2018

Document Type

Honors Project

Degree Name

Bachelor of Science

Department

Chemistry

Department Chair or Program Director

Sharpless, Charles

First Advisor

Crowder, Nicole

Major or Concentration

Biochemistry

Abstract

Click reactions are a highly versatile class of reactions that produce a diverse range of products. Copper-catalyzed azide-alkyne cycloaddition (CuAAC) click reactions require an azide and a terminal alkyne and produce a coupled product that is “clicked” through a triazole ring that can have a variety of substituents. In this work, bromo-terminated phosphonate films on copper oxide surfaces were explored as the platform for click coupling, as the terminal azide needed for the reaction can be generated through an in situ SN2 reaction with a terminal bromo group. The reactions were characterized using model reactions in solution before being conducted on modified copper oxide surfaces. Copper oxide surfaces were modified with 11- hydroxyundecylphosphonic acid (1) through the tethering by aggregation and growth (TBAG) method. Since modification of these surfaces with 1 installs a hydroxyl-terminated film (2), synthetic routes to bromination of the alcohol species using phosphorus tribromide, tosyl chloride and sodium bromide, 2,4,6-trichloro-(1,3,5)-triazine, and carbon tetrabromide were explored. Sonogashira coupling with halo-pyridine and halo-terpyridine compounds was conducted to synthesize a desired alkynyl species. CuAAC was conducted using the synthesized bromo-terminated phosphonate film and a model terminal alkyne, and Surface Reflectance Infrared analysis was used to characterize the films. Future work will focus on the use of the CuAAC to couple a synthesized pyridyl alkyne species with the bromo-terminated films as a route towards catalytic applications.

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