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Open AccessArticle

Polyfunctional Sterically Hindered Catechols with Additional Phenolic Group and Their Triphenylantimony(V) Catecholates: Synthesis, Structure, and Redox Properties

1
Toxicology Research Group, Federal State Budgetary Institution of Science “Federal Research Centre The Southern Scientific Centre of the Russian Academy of The Sciences”, Tatischeva str. 16, 414056 Astrakhan, Russia
2
Department of Chemistry, Astrakhan State Technical University, 16 Tatisheva str., Astrakhan 414056, Russia
3
G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 Tropinina str., 603137 Nizhny Novgorod, Russia
*
Author to whom correspondence should be addressed.
Academic Editor: Vito Lippolis
Molecules 2020, 25(8), 1770; https://doi.org/10.3390/molecules25081770
Received: 27 March 2020 / Revised: 9 April 2020 / Accepted: 10 April 2020 / Published: 12 April 2020
New polyfunctional sterically hindered 3,5-di-tert-butylcatechols with an additional phenolic group in the sixth position connected by a bridging sulfur atom—(6-(CH2-S-tBu2Phenol)-3,5-DBCat)H2 (L1), (6-(S-tBu2Phenol)-3,5-DBCat)H2 (L2), and (6-(S-Phenol)-3,5-DBCat)H2 (L3) (3,5-DBCat is dianion 3,5-di-tert-butylcatecolate)—were synthesized and characterized in detail. The exchange reaction between catechols L1 and L3 with triphenylantimony(V) dibromide in the presence of triethylamine leads to the corresponding triphenylantimony(V) catecholates (6-(CH2-S-tBu2Phenol)-3,5-DBCat)SbPh3 (1) and (6-(S-Phenol)-3,5-DBCat)SbPh3 (2). The electrochemical properties of catechols L1L3 and catecholates 1 and 2 were investigated using cyclic voltammetry. The electrochemical oxidation of L1L3 at the first stage proceeds with the formation of the corresponding o-benzoquinones. The second process is the oxidation of the phenolic moiety. Complexes 1 and 2 significantly expand their redox capabilities, owing to the fact that they can act as the electron donors due to the catecholate metallocycle capable of sequential oxidations, and as donors of the hydrogen atoms, thus forming a stable phenoxyl radical. The molecular structures of the free ligand L1 and complex 1 in the crystal state were determined by single-crystal X-ray analysis. View Full-Text
Keywords: redox-active ligand; catechol; thioether; antimony; X-ray; cyclic voltammetry; electronic paramagnetic resonance redox-active ligand; catechol; thioether; antimony; X-ray; cyclic voltammetry; electronic paramagnetic resonance
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MDPI and ACS Style

Smolyaninov, I.V.; Poddel’sky, A.I.; Smolyaninova, S.A.; Arsenyev, M.V.; Fukin, G.K.; Berberova, N.T. Polyfunctional Sterically Hindered Catechols with Additional Phenolic Group and Their Triphenylantimony(V) Catecholates: Synthesis, Structure, and Redox Properties. Molecules 2020, 25, 1770.

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