Near IR emitting BODIPY fluorophores with mega-stokes shifts

Martin, Aaron; Long, Conor; Forster, Robert J.; Keyes, Tia E.

doi:10.1039/c2cc31150j

Cited by 65 publications

(55 citation statements)

References 24 publications

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“…[48] The BODIPY core contains para-dimethylaminoaryl substituents but the degree to which the p-system on the aryl group can interact with the BODIPY core p-system is restricted by the presence of methyl groups at the 1-, 3-, 5-, and 7-positions (Scheme 1). In addition, a naphthyridyl unit is coupled to the BODIPY core at the meso position by a para aryl link that may or may not contain a 3-fluoro substituent.…”

Section: Introductionmentioning

confidence: 99%

Naphthyridyl‐Substituted 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) Luminophores: Photophysics and Application as Molecular Imaging Probes in Live Cells

et al. 2013

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The synthesis, optical properties, and cellular uptake of a family of 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) derivatives that incorporate a naphthyridine substituent at the 8‐position of the BODIPY core and either alkyl, bromo, or dimethylamino aryl groups at the 2‐ and 6‐positions are described. The family of compounds is classified, based on their optical properties, into two types; Class I, compounds with alkyl substituents at the 2‐ and 6‐positions show intense solvent‐independent emission, which arises from the BODIPY core with no involvement of the naphthyridine. Class II, the dimethylaminoaryl‐containing compounds exhibit charge transfer transitions that lead to NIR fluorescence and remarkably large Stokes shifts, which make them potentially attractive in bioimaging. Class II compounds exhibit complex solvent dependence. There is evidence for dual fluorescence from multiple rotamers; this is rationalized with the aid of time‐dependant density functional theory (TDDFT) calculations. A representative compound from each class was PEGylated, which rendered them water soluble, but their photophysical properties were maintained in aqueous buffered media. The uptake of the PEGylated BODIPY compounds and the nonPEGylated parent compounds by live mammalian cells was compared by using confocal fluorescence microscopy and resazurin blue cytotoxicity assays were performed. All compounds tested exhibited good cell uptake, were largely nuclear excluding, and had low toxicity at 10 μM. This is to our knowledge the first demonstration of such a mega‐Stokes‐shifted BODIPY probe in cell imaging.

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Section: Introductionmentioning

confidence: 99%

Naphthyridyl‐Substituted 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) Luminophores: Photophysics and Application as Molecular Imaging Probes in Live Cells

et al. 2013

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“…After 8 h reflux in toluene the 3,5-diphenyl-BODIPY 5a was isolated in 45%, 35% and 52% yields, respectively. These moderate yields led us to investigate Pd(dppf)Cl 2 as the catalyst, 25,26 since Pd(0)–bidentate ligand complexes are more reactive in the oxidative addition of aryl iodide. Using Pd(dppf)Cl 2 as the catalyst, BODIPY 5a was obtained from 1a in 73%, after only 2 h reflux in toluene and in the presence of K 2 CO 3 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and spectroscopic properties of β,β′-dibenzo-3,5,8-triaryl-BODIPYs

2016

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A series of β,β′-bicyclo-3,5-diaryl-BODIPYs were synthesized from the corresponding β,β′-bicyclo-3,5-diiodo-BODIPYs (1a,b) via Pd(0)-mediated Suzuki cross-coupling reactions in 82–92% yields. Subsequent aromatization with DDQ afforded the corresponding β,β′-dibenzo-aryl-BODIPYs, which showed red-shifted absorptions and emissions in the near-IR range. The dibenzo-appended BODIPYs showed characteristic 1H-, 13C-, 11B- and 19F-NMR shifts, and nearly planar conformations by X-ray crystallography.

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“…An important geometry change in the S 1 state is also expected for 3a-g because of the intramolecular charge transfer accompanying the HOMO to LUMO excitation (vide infra). It is worth noting that large Stokes shifts are of significant value in imaging and sensing applications because they eliminate self-quenching and allow the use of fluorophores at higher concentrations [26].…”

Section: Photophysical Properties Of 3a-g In Solutionmentioning

confidence: 99%

Solution-and solid-state emitters with large Stokes shifts combining pyrene and 4-hydroxythiazole fluorophores

et al. 2015

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Near IR emitting BODIPY fluorophores with mega-stokes shifts

Abstract: A novel Near Infra-Red emitting BODIPY derivative is presented which exhibits the largest Stokes shift thus far reported for a BODIPY compound.

Cited by 65 publications

References 24 publications

Naphthyridyl‐Substituted 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) Luminophores: Photophysics and Application as Molecular Imaging Probes in Live Cells

Naphthyridyl‐Substituted 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) Luminophores: Photophysics and Application as Molecular Imaging Probes in Live Cells

Synthesis and spectroscopic properties of β,β′-dibenzo-3,5,8-triaryl-BODIPYs

Solution-and solid-state emitters with large Stokes shifts combining pyrene and 4-hydroxythiazole fluorophores

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