Affiliation:
1. Department of Chemistry and Biochemistry, Berry College, Mount Berry, GA 30149, USA
Abstract
Urazolyl radicals are a class of persistent nitrogen-centered radicals. In a previous work, we successfully formed self-assembled monolayers of substituted urazolyl radicals on gold surfaces. To extend the scope of these investigations, we sought to form a self-assembled monolayer using a urazolyl radical species that we knew existed predominantly in the dimerized N-N form instead of existing predominantly as free N-centered radical species, as had previously been investigated. We successfully synthesized the precursor urazole compound needed to generate the desired urazolyl radical, and completely characterized its structure. Most importantly, it was determined that the alkyne functional group that is needed to adhere to the gold surface remained intact. Unfortunately, however, we only obtained ambiguous results from attempts at forming self-assembled monolayers of this species on gold.
Subject
Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry
Reference6 articles.
1. Efficient Routes for the Preparation of Urazole Radical Self-Assembled Monolayers on Gold Surfaces;Crivillers;J. Phys. Chem.,2022
2. Persistent Cyclic Diacylhydrazyl Radicals from Urazoles and Pyrazolidine-3,5-diones;Pirkle;J. Org. Chem.,1978
3. Probing the Dynamic Covalent Chemistry Behavior of Nitrogen-Centered Di- and Triurazole Radicals;Breton;J. Org. Chem.,2020
4. 1-(4-{[3,5-bis({[3,5-Dimethyl-4-(4-methyl-3,5-dioxo-1,2,4-triazolindin-1-yl)-phenoxy]methyl})phenyl]methoxy}-2,6-dimethylphenyl)-4-methyl-1,2,4-triazolidine-3,5-dione;Breton;Molbank,2023
5. Directional Molecular Transportation Based on a Catalytic Stopper-Leaving Rotaxane System;Meng;J. Am. Chem. Soc.,2016