Redox-controlled chalcogen and pnictogen bonding: the case of a sulfonium/stibonium dication as a preanionophore for chloride anion transport.

Chemical Science
Gyeongjin Park, François P Gabbaï

Abstract

Our interest in the chemistry of tunable chalcogen and pnictogen bond donors as Lewis acidic platforms for the complexation and transport of anions has led us to investigate examples of such compounds that can be activated by redox events. Here, we describe the synthesis of [o-MePhS(C6H4)SbPh3]2+ ([3]2+) and [o-MePhS(C6H4)Sb(p-Tol)3]2+ ([4]2+), two dicationic stibonium/sulfonium bifunctional Lewis acids which were obtained by methylation of the phenylthioether derivatives [o-PhS(C6H4)SbPh3]+ ([1]+) and [o-PhS(C6H4)Sb(p-Tol)3]+ ([2]+), respectively. An evaluation of the chloride anion transport properties of these derivatives using chloride-loaded POPC unilamellar vesicles shows that the activity of the monocations [1]+ and [2]+ greatly exceeds that of the dications [3]2+ and [4]2+, a phenomenon that we assign to the higher lipophilicity of the monocationic compounds. Harnessing this large transport activity differential, we show that [4]2+ can be used as a prechloridophore that is readily activated by reduction of the sulfonium moiety. Indeed, [4]2+ reacts with GSH to afford [2]+ as an active transporter. This activation, which has been monitored in aqueous solution, can also be carried out in situ, in the presence of the chlor...Continue Reading

References

Feb 1, 2007·Chemical Society Reviews·Anthony P DavisBradley D Smith
Jun 6, 2009·Angewandte Chemie·Youngmin KimFrançois P Gabbaï
Jan 8, 2010·Organic Letters·Youngmin KimFrançois P Gabbaï
Jun 4, 2010·Chemical Communications : Chem Comm·Philip A Gale
Aug 7, 2010·Chemical Communications : Chem Comm·Casey R WadeFrançois P Gabbaï
Sep 8, 2010·Chemical Society Reviews·Jeffery T DavisRoberto Quesada
Oct 23, 2010·Nature Chemistry·Haiyan Zhao, François P Gabbaï
Jan 25, 2011·Journal of the American Chemical Society·Sabir HussainAnthony P Davis
Feb 22, 2011·Organic Letters·Haiyan Zhao, François P Gabbaï
Mar 11, 2011·Chemical Society Reviews·Stefan MatileAndrea Fin
Aug 19, 2011·Journal of the American Chemical Society·Nathalie BusschaertPhilip A Gale
Oct 15, 2011·Angewandte Chemie·Andreas Vargas JentzschStefan Matile
Apr 26, 2012·Chemical Communications : Chem Comm·Vittorio SaggiomoRoberto Quesada
Jun 21, 2012·Nature Communications·Andreas Vargas JentzschStefan Matile
Sep 8, 2012·Journal of the American Chemical Society·Iou-Sheng KeFrançois P Gabbaï
Apr 4, 2013·Accounts of Chemical Research·Andreas Vargas JentzschStefan Matile
Apr 5, 2013·Accounts of Chemical Research·Philip A GaleRoberto Quesada
May 2, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Santiago Alvarez
Nov 27, 2014·Angewandte Chemie·Masato Hirai, François P Gabbaï
Feb 24, 2015·Chemical Communications : Chem Comm·Michael J Spooner, Philip A Gale
Jan 11, 2016·Chemistry : a European Journal·Sophie J EdwardsAnthony P Davis
Jul 20, 2016·Journal of the American Chemical Society·Sebastian BenzStefan Matile
Dec 10, 2016·Journal of the American Chemical Society·Tanmoy SahaPinaki Talukdar
Mar 10, 2017·Angewandte Chemie·Sopan Valiba Shinde, Pinaki Talukdar
Apr 6, 2017·Chemical Society Reviews·Philip A GaleRoberto Quesada
Jul 8, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Kamran T MahmudovArmando J L Pombeiro
Jul 7, 2018·Physical Chemistry Chemical Physics : PCCP·Igor MarquesVítor Félix
Aug 1, 2018·Accounts of Chemical Research·Xin WuPhilip A Gale
Aug 29, 2018·Angewandte Chemie·Mengxi YangFrançois P Gabbaï
Sep 19, 2018·Angewandte Chemie·Lukas VogelStefan M Huber
Jan 9, 2019·Journal of the American Chemical Society·Lucia M LeeStefan Matile
May 14, 2019·Journal of the American Chemical Society·Alex J PlajerDominic S Wright
Dec 27, 2019·Journal of the American Chemical Society·Alex J PlajerDominic S Wright
Jun 26, 2020·Angewandte Chemie·Mohamed FaresPhilip A Gale

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Citations

May 15, 2021·Organic & Biomolecular Chemistry·Di YouFrançois P Gabbaï
May 21, 2021·Chemistry : a European Journal·Laura E BickertonMatthew J Langton
Jun 23, 2021·Physical Chemistry Chemical Physics : PCCP·Lucas de Azevedo SantosF Matthias Bickelhaupt
Nov 25, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Vanessa M GonzalezFrançois P Gabbaï

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