Off-campus UMass Amherst users: To download campus access dissertations, please use the following link to log into our proxy server with your UMass Amherst user name and password.

Non-UMass Amherst users: Please talk to your librarian about requesting this dissertation through interlibrary loan.

Dissertations that have an embargo placed on them will not be available to anyone until the embargo expires.

Document Type

Open Access Dissertation

Degree Name

Doctor of Philosophy (PhD)

Degree Program

Chemistry

Year Degree Awarded

2016

Month Degree Awarded

May

First Advisor

James Chambers

Second Advisor

Nathan Schnarr

Third Advisor

E. Bryan Coughlin

Fourth Advisor

Sankaran Thayumanavan

Subject Categories

Molecular Biology | Organic Chemistry

Abstract

Copper catalyzed cycloaddition of terminal alkynes and azides has revolutionized the field of bioconjugate chemistry. Unfortunately, typical copper catalysts are known to disrupt relevant biological systems, so it has become necessary to develop new, copper-free methods that are less cytotoxic. particular interest are "click" probes which can be activated with an outside light source, giving the user spatial and temporal control over the system being investigated. We have developed a method in which an aryl diazonium salt is rapidly generated using photolysis of the triazene functional group, and subsequently coupled with an electron rich aromatic nucleophile to yield an azobenzene. Benefits of this method over current photo-click methods include the fast rate of photolysis and almost instantaneous reaction times with subsequent reaction partners, allowing for minimal exposure to a UV light source and little to no incubation time with reactive partners, respectively

Share

COinS