Dynamic Covalent Bond: Modes of Activation of the C—ON Bond in Alkoxyamines

Dynamic Covalent Bond: Modes of Activation of the C—ON Bond in Alkoxyamines Full article

Journal

Progress in Polymer Science
ISSN: 0079-6700 , E-ISSN: 1873-1619

Output data

Year: 2023, Volume: 144, Pages: 101726 Pages count : 25 DOI: 10.1016/j.progpolymsci.2023.101726

Authors

Audran Gérard ¹ , Bagryanskaya Elena G. ² , Bikanga Raphaël ³ , Coote Michelle L. ⁴ , Guselnikova Olga ⁵ , Hammill Chelsey L. ⁶ , Marque Sylvain R.A. ¹ , Mellet Philippe ^7,8 , Postnikov Pavel S. ^5,9

Affiliations

1	Aix Marseille Univ, CNRS, ICR, UMR 7273, Case 551, Avenue Escadrille Normandie-Niemen, Cedex 20, 13397 Marseille, France
2	b N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Novosibirsk 630090, Russia
3	Université des Sciences et techniques de Masuku, LASNSOM, B.P. 901 Franceville, Gabon
4	Institute for Nanoscale Science & Technology, Flinders University, Adelaide, South Australia, 5042, Australia
5	Research School of Chemistry & Applied Biomedical Sciences, National Research Tomsk Polytechnic University, Lenin Avenue 30, Tomsk 634050, Russia
6	Research School of Chemistry, Australian National University, Canberra ACT 2601, Australia
7	Magnetic Resonance of Biological Systems, UMR 5536 CNRS-University of Bordeaux, Bordeaux 33076, France
8	INSERM, Bordeaux 33000, France
9	Department of Solid-State Engineering, University of Chemistry and Technology Prague, Technická 5,166 28 Prague, Czech Republic

The materials of future depend a lot on properties that are due to “non stable” molecules. Hence, Dynamic Covalent Bonds (DCB) are covalent bonds that are labile under specific stimuli and are integral to the design of next generation materials. Alkoxyamines R1R2NO—R3 exhibit a unique C—O DCB that is nonsymmetric between the adjacent O- and C-atoms. This bond can be cleaved homolytically, heterolytically and mesolytically in response to a wide variety of physical, chemical and biological stimuli, and the kinetics and thermodynamics of cleavage can be tuned on-demand by varying the structure of R1, R2 and R3. Alkoxyamines are easily incorporated into polymers via nitroxide mediated polymerisation (NMP) however, their dynamic covalent properties are yet to be fully exploited in materials sciences. This is in part because reports on C—ON activation are scattered through the broader synthetic, physical and biological chemistry literature, and a comprehensive review of them has been lacking. Herein, 20 leading C—ON activation processes using UV-light, surface plasmon resonance, magnetothermy, electrochemistry, chemical oxidation, protonation, non-covalent bonding, sonication, enzymatic activation among others, are presented and discussed, along with primary examples of their application.

Audran G. , Bagryanskaya E.G. , Bikanga R. , Coote M.L. , Guselnikova O. , Hammill C.L. , Marque S.R.A. , Mellet P. , Postnikov P.S.
Dynamic Covalent Bond: Modes of Activation of the C—ON Bond in Alkoxyamines
Progress in Polymer Science. 2023. V.144. P.101726. DOI: 10.1016/j.progpolymsci.2023.101726 WOS Scopus РИНЦ

Submitted:	Jan 18, 2023
Accepted:	Jul 4, 2023
Published online:	Jul 5, 2023

Web of science	WOS:001049592500001
Scopus	2-s2.0-85165536217
Elibrary	62452671
OpenAlex	W4383215330