917201-08-2Relevant articles and documents
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.
Use of F-BODIPYs as a protection strategy for dipyrrins: Optimization of BF2 removal
Smithen, Deborah A.,Baker, Alexander E. G.,Offman, Matthew,Crawford, Sarah M.,Cameron, T. Stanley,Thompson, Alison
experimental part, p. 3439 - 3453 (2012/05/20)
We recently reported the first general method for the deprotection of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) involving a microwave-assisted procedure for the removal of the BF2 moiety, and liberation of the corresponding free-base dipyrrin. Further optimization of the reaction has resulted in a more convenient and accessible protocol. The availability of this new methodology enables BF2-complexation to be used as a dipyrrin protection strategy. Herein lies a detailed examination of the deprotection reaction, with a view to optimization and gaining mechanistic insight, and its application in facilitating a multistep synthesis of pyrrolyldipyrrins.
Conversion of 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacenes (F-BODIPYs) to dipyrrins with a microwave-promoted deprotection strategy
Crawford, Sarah M.,Thompson, Alison
supporting information; experimental part, p. 1424 - 1427 (2010/06/15)
Chemical eqation presented 4,4-Difluoro-4-bora-3a,4a-diaza-s- indacenes (F-BODIPYs) have been deprotected to give the corresponding free-base dipyrrins by heating a solution of the F-BODIPY in tert-butanol under 600 W of microwave irradiation in the presence of 6 equiv of potassium tert-butoxide for 40 min at 92 C. Investigations of BODIPY modification at the meso position have also been undertaken and a meso-butyl product has been isolated.
The first series of alkali dipyrrinato complexes
Ali, Adeeb Al-Sheikh,Cipot-Wechsler, Judy,Crawford, Sarah M.,Selim, Omar,Stoddard, Rhonda L.,Cameron, T. Stanley,Thompson, Alison
, p. 725 - 735 (2010/09/16)
The first series of alkali dipyrrinato complexes is reported, encompassing lithium, sodium, and potassium salts of meso-unsubstituted and meso-aryl-substituted derivatives. By varying the substituents at the meso position, the intermolecular distance betw
Design and development of a new pyrromethene dye with improved photostability and lasing efficiency: Theoretical rationalization of photophysical and photochemical properties
Mula, Soumyaditya,Ray, Alok K.,Banerjee, Manas,Chaudhuri, Tandrima,Dasgupta, Kamalesh,Chattopadhyay, Subrata
, p. 2146 - 2154 (2008/09/19)
(Chemical Equation Presented) In an attempt to develop a photostable and efficient pyrromethene compound for use in liquid dye lasers, three congeners of the commercially available pyrromethene 567 (PM567) laser dye were synthesized and their photophysical properties, lasing efficiencies, and photochemical stabilities were studied. In general the presence of an aryl group at C-8 of the pyrromethene chromophore increased the photostability. One of the congeners possessing a C-8 trimethoxyphenyl moiety showed significantly improved lasing parameters than PM567. Compared to PM567, the photochemical stability of the new dye was 2-fold, while it showed an equivalent lasing efficiency to that of PM567 at a significantly lower concentration. The increased photostability of these new dye molecules could be explained by theoretical calculation on their capacity to generate singlet oxygen (1O2) and probability of reaction with 1O2. Our calculations were in agreement with the experimental results and indicated that a systematic design of new derivatives of pyrromethene chromophore might lead to improved laser dye molecules.
Highly Sensitive Fluorescence Probes for Nitric Oxide Based on Boron Dipyrromethene Chromophore - Rational Design of Potentially Useful Bioimaging Fluorescence Probe
Gabe, Yu,Urano, Yasuteru,Kikuchi, Kazuya,Kojima, Hirotatsu,Nagano, Tetsuo
, p. 3357 - 3367 (2007/10/03)
Boron dipyrromethene (BODIPY) is known to have a high quantum yield (φ) of fluorescence in aqueous solution but has not been utilized much for biological applications, compared to fluorescein. We developed 8-(3,4-diaminophenyl)-2,6-bis(2-carboxyethyl)-4,4
