Design of a thermally controlled sequence of triazolinedione-based click and transclick reactions

Chemical Science
Hannes A HouckFilip E Du Prez

Abstract

The reaction of triazolinediones (TADs) and indoles is of particular interest for polymer chemistry applications, as it is a very fast and irreversible additive-free process at room temperature, but can be turned into a dynamic covalent bond forming process at elevated temperatures, giving a reliable bond exchange or 'transclick' reaction. In this paper, we report an in-depth study aimed at controlling the TAD-indole reversible click reactions through rational design of modified indole reaction partners. This has resulted in the identification of a novel class of easily accessible indole derivatives that give dynamic TAD-adduct formation at significantly lower temperatures. We further demonstrate that these new substrates can be used to design a directed cascade of click reactions of a functionalized TAD moiety from an initial indole reaction partner to a second indole, and finally to an irreversible reaction partner. This controlled sequence of click and transclick reactions of a single TAD reagent between three different substrates has been demonstrated both on small molecule and macromolecular level, and the factors that control the reversibility profiles have been rationalized and guided by mechanistic considerations suppor...Continue Reading

References

May 24, 2003·Organic Letters·Phil S BaranE J Corey
Jul 11, 2007·Chemical Society Reviews·John E Moses, Adam D Moorhouse
Feb 19, 2010·Angewandte Chemie·Charles E Hoyle, Christopher N Bowman
Dec 7, 2010·Angewandte Chemie·Christopher Barner-KowollikWim Van Camp
Sep 17, 2011·Science·Johnathan N BrantleyChristopher W Bielawski
Nov 3, 2011·Journal of the American Chemical Society·Steffen MüllerBenjamin List
Nov 30, 2013·Chemical Society Reviews·Adam WilsonStefan Matile
Mar 25, 2014·Advanced Materials·Kim K OehlenschlaegerChristopher Barner-Kowollik
Sep 9, 2015·Angewandte Chemie·Oliver RolingFilip E Du Prez
Feb 24, 2016·Chemical Reviews·Kevin De BruyckerFilip E Du Prez

❮ Previous
Next ❯

Citations

Dec 1, 2017·Nature Communications·Hannes A HouckChristopher Barner-Kowollik
Apr 25, 2020·Advanced Science·Joshua O HollowayFilip E Du Prez
Jan 23, 2018·Langmuir : the ACS Journal of Surfaces and Colloids·William LaureJoël Lyskawa
Jun 27, 2019·Journal of the American Chemical Society·Hannes A HouckChristopher Barner-Kowollik

❮ Previous
Next ❯

Methods Mentioned

BETA
NMR

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.