Photostable Polynuclear Ruthenium(II) Photosensitizers Competent for Dehalogenation Photoredox Catalysis at 590 nm

Journal of the American Chemical Society
Simon CerfontaineLudovic Troian-Gautier

Abstract

Higher nuclearity photosensitizers produced dehalogenation yields greater than 90% in the reported [Ru(bpy)3]2+-mediated dehalogenation of 4-bromobenzyl-2-chloro-2-phenylacetate to 4-bromobenzyl-2-phenylacetate with orange light in 7 h, whereas after 72 h yields of 49% were obtained with [Ru(bpy)3]2+. Dinuclear (D1), trinuclear (T1), and quadrinuclear (Q1) ruthenium(II) 2,2'-bipyridine based photosensitizers were synthesized, characterized, and investigated for their photoreactivity. Three main factors were shown to lead to increased yields (i) the red-shifted absorbance of polynuclear photosensitizers, (ii) the more favorable driving force for electron transfer, characterized by more positive E1/2(Ru2+*/+), and (iii) the smaller population of the 3MC state (<0.5% for D1, T1 and Q1 vs 48% for [Ru(bpy)3]2+ at room temperature). Collectively, these results highlight the potential advantages of using polynuclear photosensitizers in phototriggered redox catalysis reactions.

References

Nov 14, 2002·Chemical Reviews·Francisco AlonsoMiguel Yus
Jan 30, 2007·Journal of the American Chemical Society·George B ShawLin X Chen
Jun 26, 2009·Journal of the American Chemical Society·Jagan M R NarayanamCorey R J Stephenson
Nov 12, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Giuseppina La GangaFausto Puntoriero
Sep 30, 2010·Angewandte Chemie·Matthias NeumannKirsten Zeitler
Aug 20, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Kathleen ServatyAndrée Kirsch-De Mesmaeker
Oct 4, 2012·Journal of the American Chemical Society·Megan S LazorskiC Michael Elliott
Apr 25, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ludovic Troian-Gautier, Cécile Moucheron
Dec 23, 2014·Green Chemistry : an International Journal and Green Chemistry Resource : GC·Nicholas A IsleyBruce H Lipshutz
Jun 9, 2016·The Journal of Organic Chemistry·Saemi O PoelmaJavier Read de Alaniz
Jun 11, 2016·Chemical Reviews·Nathan A Romero, David A Nicewicz
Aug 2, 2016·The Journal of Organic Chemistry·Megan H ShawDavid W C MacMillan
Nov 24, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Emanuele La MazzaSebastiano Campagna
Mar 30, 2018·Journal of the American Chemical Society·Guocan LiGerald J Meyer
Oct 24, 2018·Journal of the American Chemical Society·Oliver S Wenger
Jan 24, 2019·Journal of the American Chemical Society·Christoph KerzigOliver S Wenger
Mar 12, 2019·Chemical Reviews·Ludovic Troian-GautierGerald J Meyer
Jul 4, 2019·Organic & Biomolecular Chemistry·Peng-Zi WangWen-Jing Xiao
Jul 30, 2019·Journal of the American Chemical Society·Carla M MortonErik J Alexanian
Jan 17, 2020·Chemical Society Reviews·Guangfu LiMartin R Bryce

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Citations

May 29, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Simon CerfontaineBenjamin Elias
Aug 11, 2020·The Journal of Chemical Physics·Sara A M WehlinGerald J Meyer
Aug 7, 2020·Chemical Communications : Chem Comm·Francisco J BallesterJosé Ruiz
Jul 27, 2021·ACS Applied Materials & Interfaces·Alexandra GelléAudrey Moores
Dec 23, 2020·Inorganic Chemistry·Simon CerfontaineBenjamin Elias
Jan 13, 2021·Journal of the American Chemical Society·Jakob B BilgerOliver S Wenger
Sep 17, 2021·Journal of the American Chemical Society·Akin AydoganLudovic Troian-Gautier

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