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Relevant academic research and scientific papers

Some observations relating to the stability of the BODIPY fluorophore under acidic and basic conditions

4,4-Difluoro-4-bora-1,3,5,7-tetramethyl-2,6-diethyl-8-methyl-3a, 4a-diaza-s-indacene (BODIPY) fluorophore was transformed into its corresponding 4,4-dimethyl, 4,4-dimethoxy and 4,4-diphenyl analogues. The stabilities of these BODIPY fluorophores in acidic

Synthesis and photophysical properties of borondipyrromethene dyes bearing aryl substituents at the boron center

Several borondipyrromethene (Bodipy) dyes bearing an aryl nucleus linked directly to the boron center have been prepared under mild conditions. The choice of Grignard or lithio organo-metallic reagents allows the isolation of B(F)(aryl) or B(aryl)2/

First highly efficient and photostable e and Ca derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) as dye lasers in the liquid phase, thin films, and solid-state rods

A new library of E- and C-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives has been synthesized through a straightforward protocol from commercially available BODIPY complexes, and a systematic study of the photophysical properties and lase

Heavy-Atom Free spiro Organoboron Complexes As Triplet Excited States Photosensitizers for Singlet Oxygen Activation

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.

Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water

A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with a wide range of functional groups. Without the need for a strong inorganic base or an expensive noble-metal catalyst, this process can be applied to the efficient preparation of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.

Masking and demasking strategies for the BF2-BODIPYs as a tool for BODIPY fluorophores

An efficient and chemoselective route for transforming BF2-BODIPYs to Et2B-BODIPYs (masking) was developed using Et2AlCl. The Et groups can be easily replaced with F atoms using BF3·Et2O in moist CH2Cl2 to regenerate the BF2-BODIPYs (demasking). The masking-demasking strategy is very useful for synthesizing functionalized BODIPYs via nucleophilic and reductive reactions. The masking strategy was used to synthesize a BODIPY dimer by McMurry coupling of a formyl Et2B-BODIPY, while a new BODIPY with an asymmetrically substituted B-center was synthesized using the demasking strategy.

New fluorescent aryl- or ethynylaryl-boron-substituted indacenes as promising dyes

A generic design principle based on the use of organometallic (Li or Mg) reagents for the substitution of the fluoro ligands in difluoroboradiazaindacene is described. A library of compounds bearing various substituents (butyl, phenyl, naphthyl, pyrenyl, ethynylnaphthyl, ethynylfluorenyl, ethynylcarbazoyl, ethynylperylenyl, ethynylthiophenyl and ethynylterpyridinyl) has been prepared and characterized. Electrochemical and photochemical measurements show that these novel dyes remain redox-active and strongly luminescent. They offer an interesting perspective for applications in labelling and electroluminescence. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.