Molecular Design and Application of a Pro-fluorescent Thiophene-Based o-Nitrobenzyl Photolabile Protecting Groups for the Synthesis of Hydroxamic Acids
Disciplines
Materials Chemistry | Organic Chemistry
Abstract (300 words maximum)
Hydroxamic acids (HAs) have a wide range of applications, including use as dyes in dye-sensitized solar cells, precursors in the production of chemotherapy medicines for various cancers, and metal chelators in the removal of hazardous metals from seawater. Nonetheless, they are notoriously difficult to synthesize and purify, resulting in a wide range of polysubstituted by-products and low HA yield during their synthesis. Chemists have learned to solve this difficulty by using protecting groups (PGs) to temporarily inhibit the reactivity of functional groups such as HAs. Despite this advantage, PGs must be removed with harsh conditions which may destroy the protected HA product. Selective PG removal is especially problematic when many PGs that are unstable under comparable conditions are used on the same compound. Photolabile protecting groups (PPGs) such as ortho-nitrobenzyl (o-NB) based PPGs have become a popular tool to solve the challenges of selective PG removal because they can be selectively removed using only light, which is a less harsh condition. In this study, we describe the molecular design and synthesis of a new class of o-NB PPGs as a solution to the limitations of HA synthesis and purification. This new class of PPGs can be selectively cleaved with light and produce a diagnostic fluorescent by-product that can be seen with the naked eye and used to quantify the amount of the released HA product. The stability of the new PPGS will be assessed by determining their shelf-life stability. Herein, we are reporting the first and only example of thiophene-based PPGs used to synthesize HAs that produce a diagnostic fluorescent by-product used to quantify the amount of the released HA product.
Academic department under which the project should be listed
CSM - Chemistry and Biochemistry
Primary Investigator (PI) Name
Carl Saint-Louis
Molecular Design and Application of a Pro-fluorescent Thiophene-Based o-Nitrobenzyl Photolabile Protecting Groups for the Synthesis of Hydroxamic Acids
Hydroxamic acids (HAs) have a wide range of applications, including use as dyes in dye-sensitized solar cells, precursors in the production of chemotherapy medicines for various cancers, and metal chelators in the removal of hazardous metals from seawater. Nonetheless, they are notoriously difficult to synthesize and purify, resulting in a wide range of polysubstituted by-products and low HA yield during their synthesis. Chemists have learned to solve this difficulty by using protecting groups (PGs) to temporarily inhibit the reactivity of functional groups such as HAs. Despite this advantage, PGs must be removed with harsh conditions which may destroy the protected HA product. Selective PG removal is especially problematic when many PGs that are unstable under comparable conditions are used on the same compound. Photolabile protecting groups (PPGs) such as ortho-nitrobenzyl (o-NB) based PPGs have become a popular tool to solve the challenges of selective PG removal because they can be selectively removed using only light, which is a less harsh condition. In this study, we describe the molecular design and synthesis of a new class of o-NB PPGs as a solution to the limitations of HA synthesis and purification. This new class of PPGs can be selectively cleaved with light and produce a diagnostic fluorescent by-product that can be seen with the naked eye and used to quantify the amount of the released HA product. The stability of the new PPGS will be assessed by determining their shelf-life stability. Herein, we are reporting the first and only example of thiophene-based PPGs used to synthesize HAs that produce a diagnostic fluorescent by-product used to quantify the amount of the released HA product.