Synthesis of 4,4′-functionalized BODIPYs from dipyrrins

Nguyen, Alex L.; Fronczek, Frank R.; Smith, Kevin M.; Vicente, M. Graça H.

doi:10.1016/j.tetlet.2015.09.119

Cited by 11 publications

(7 citation statements)

References 29 publications

(39 reference statements)

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“…[19] Surprisingly,a longside the expected BODIPY (rac)-2,w eo bserved the formation, in 8% yield, of an unsymmetrical helically chiral BODIPY 3 containing ap reviously unreported tetradentate" confused" N,N,O,C-boron-chelation motif,i nw hich the binding of one of the 3,5-ortho-phenolic substituents is inverted in comparison to that of the parentc ompound 2. [20][21][22] Switching the starting materialt ot he potential more reactive 3,5-dibromo-BODIPY 1b resulted an improved 36 %y ield of (rac)-3.W ep ropose that (rac)-3 is formed through ac omplex series of reaction steps involving:M etathesis of the BF 2 group with the boron of (2-hydroxyphenyl)boronic acid, nucleophilic aromatic substitution (S N Ar) of aryl bromide by the phenolic hydroxy group, Suzuki couplingw ith as econd equivalent of (2-hydroxyphenyl)boronica cid and finally chelation of the boron by the free phenolic hydroxy group (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Circularly Polarised Luminescence from Helically Chiral “Confused” N,N,O,C‐Boron‐Chelated Dipyrromethenes (BODIPYs)

Clarke

Alsimaree

et al. 2017

ChemPhotoChem

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Chiral organic fluorophores have significant promise in the development of efficient emitters of circularly polarized light. Herein we describe a helically chiral boron dipyrromethene (BODIPY) with a hitherto unreported N,N,O,C‐boron‐chelation motif, synthesised by means of a one‐pot boron metathesis, nucleophilic aromatic substitution (SNAr), Suzuki coupling, boron chelation, cascade reaction. Resolution of the racemic BODIPY (by preparative HPLC on a chiral stationary phase) allowed examination of the chiroptical properties of the resulting enantiomers (λmax(abs)=593 nm, λmax(em)=622 nm, ϵ=30 000 m−1 cm−1, φF=0.49, |glum|=3.7×10−3 (hexane)). This is the first example of circularly polarised emission from a non‐C2‐symmetric helically chiral N,N,O,C‐BODIPY and as such provides a valuable benchmark for future developments in this compound series.

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Section: Resultsmentioning

confidence: 99%

Circularly Polarised Luminescence from Helically Chiral “Confused” N,N,O,C‐Boron‐Chelated Dipyrromethenes (BODIPYs)

Clarke

Alsimaree

et al. 2017

ChemPhotoChem

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“…Many functional groups, however, were not tolerated in this method. Alternatively, successive substitution reactions of organo dichloroboron BCl 2 R by a dipyrromethene and fluoride produced BFR-BODIPY (Figure b), although BFPh-BODIPY is the sole example synthesized by this method. Here, we disclose a versatile synthesis of BFR-BODIPY through convergent coupling between BF 2 R and dipyrromethene that proceeded under mild conditions with high functional group tolerance (Figure c).…”

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confidence: 99%

Convergent and Functional-Group-Tolerant Synthesis of B-Organo BODIPYs

et al. 2018

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Boron-dipyrromethenes (BODIPYs) are one of the most important fluorescent materials. Despite their potential unique properties, however, B,B-fluoro-organo BODIPYs (BFR-BODIPYs) possessing an organo group (R) on the boron center have not been studied in detail, due in part to challenges related to their synthesis. In this paper, a convergent synthesis of BFR-BODIPYs operative under mild conditions is reported. Conversions of the thus-synthesized functionalized BFR-BODIPYs by cross-coupling, condensation, and S N 2 reactions at the R group are also demonstrated.

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“…We then turned our attention to borondiphenyl BODIPY 15 , a more chemically robust yet fluorescent BODIPY analogue [ 40 ]. Access to 15 was also affected by slightly modifying our one-pot procedure [ 38 ], from phthalide and pyrrole, by simply replacing BF 3 .OEt 2 by B(Ph) 3 in the borondipyrromethene ring closing reaction ( Scheme 2 b) [ 41 ].…”

Section: Resultsmentioning

confidence: 99%

A Concise Synthesis of a BODIPY-Labeled Tetrasaccharide Related to the Antitumor PI-88

et al. 2021

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A convergent synthetic route to a tetrasaccharide related to PI-88, which allows the incorporation of a fluorescent BODIPY-label at the reducing-end, has been developed. The strategy, which features the use of 1,2-methyl orthoesters (MeOEs) as glycosyl donors, illustrates the usefulness of suitably-designed BODIPY dyes as glycosyl labels in synthetic strategies towards fluorescently-tagged oligosaccharides.

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Synthesis of 4,4′-functionalized BODIPYs from dipyrrins

Cited by 11 publications

References 29 publications

Circularly Polarised Luminescence from Helically Chiral “Confused” N,N,O,C‐Boron‐Chelated Dipyrromethenes (BODIPYs)

Circularly Polarised Luminescence from Helically Chiral “Confused” N,N,O,C‐Boron‐Chelated Dipyrromethenes (BODIPYs)

Convergent and Functional-Group-Tolerant Synthesis of B-Organo BODIPYs

A Concise Synthesis of a BODIPY-Labeled Tetrasaccharide Related to the Antitumor PI-88

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