1291101-58-0Relevant academic research and scientific papers
Heavy-Atom Free spiro Organoboron Complexes As Triplet Excited States Photosensitizers for Singlet Oxygen Activation
Blacha-Grzechnik, Agata,Durka, Krzysztof,Marek-Urban, Paulina H.,Paplińska, Klaudia,Urban, Mateusz,Wiklińska, Magdalena,Wo?niak, Krzysztof
, p. 12714 - 12722 (2021/09/18)
Herein, we present a new strategy for the development of efficient heavy-atom free singlet oxygen photosensitizers based on rigid borafluorene scaffolds. Physicochemical properties of borafluorene complexes can be easily tuned through the choice of ligand, thus allowing exploration of numerous organoboron structures as potent 1O2 sensitizers. The singlet oxygen generation quantum yields of studied complexes vary in the range of 0.55-0.78. Theoretical calculations reveal that the introduction of the borafluorene moiety is crucial for the stabilization of a singlet charge transfer state, while intersystem crossing to a local triplet state is facilitated by orthogonal donor-acceptor molecular architecture. Our study shows that quantitative oxidation of selected organic substrates can be achieved in 20-120 min of irradiation with only 0.05 mol % loading of a photocatalyst.
Cl-BODIPYs: A BODIPY class enabling facile B-substitution
Lundrigan, Travis,Crawford, Sarah M.,Cameron, T. Stanley,Thompson, Alison
, p. 1003 - 1005 (2012/02/16)
Cl-BODIPYs, synthesized in high yields from dipyrrins under air- and moisture-free conditions, are extremely facile to substitution at boron compared to their corresponding F-BODIPYs, opening up a new route to BODIPYs functionalized at boron.
Investigations into the nucleophilic meso-substitution of f-bodipys and improvements to the synthesis of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Crawford, Sarah M.,Thompson, Alison
experimental part, p. 311 - 322 (2011/04/22)
A series of three F-BODIPYs, with varying levels of steric crowding about the meso-position were selected to investigate nucleophilic meso-substitution of F-BODIPYs. The synthesis of one of these F-BODIPYs, 4,4-difluoro-4-bora-3a,4a- diaza-s-indacene (totally unsubstituted dipyrrin skeleton), was optimized to give higher yields over routine literature procedures. This modified procedure involves oxidation of a dipyrromethane using p-chloranil, instead of DDQ, to give a dipyrrin which is then trapped in situ as its BF2 complex. Nucleophilic meso-alkylation of the series of F-BOIDPYs with n-butyllithium gave meso-butyl F-BODIPYs in moderate to good yields. This work represents a new, synthetically viable method for the synthesis of meso-alkylated F-BODIPYs. Extension of the nucleophilic substitution methodology to meso-arylation was possible. However, the reaction was unselective: substitution at boron, to give the boron-diaryl C-BOIDPYs, occurred preferentially to nucleophilic meso-substitution and thus a mixture of products was obtained. The Japan Institute of Heterocyclic Chemistry.
