Synthesis of BODIPY dyes through postfunctionalization of the boron dipyrromethene core

Boens, Noël; Verbelen, Bram; Ortiz, María J.; Jiao, Lijuan; Dehaen, Wim

doi:10.1016/j.ccr.2019.213024

Cited by 266 publications

(184 citation statements)

References 551 publications

(502 reference statements)

Supporting

Mentioning

180

Contrasting

Unclassified

Order By: Relevance

“…The use of electrophilic NIS as promotor precluded the use of BODIPYs 6 and 7 as acceptors, owing to the nucleophilicity of the BODIPYs at positions C-2a nd C-6. [34] On the other hand, desilylation of BODIPY-glycosides 20 and 23,l eading to the hydroxyl derivatives 21 and 24 (Scheme 3E and F, respectively), could be efficientlye ffected by treatment with HCl/methanol, as seen before ( Table 1, entry 12). Finally,a ctivation of phenyl thioglycoside 25 with the thiophilic promotor system Ph 2 SO/Tf 2 O, [46] in the presence of 4-tertbutyl-2,6-di-methylpyridine (TBMP), was also possible and yielded glucoside 26 in 68 %y ield, as an (8:1) a/b anomeric mixture with the a-anomer prevailing.…”

Section: Bodipysand Glycosylation Reactionsmentioning

confidence: 66%

“…Thus, derivatives 6 and 7,a nd 8 and 9 differed in the substitution at boron (F vs. CN). Compounds 8 and 9 possessed ethyl substituents at C-2 and C-6 (when compared to 6 and 7)a imed at shielding the BODIPY core towards the electrophilicr eagents [34] required in the activation of some of the glycosyl donors evaluated in this work. Additionally,s ince our planned studies also include the stabilityo ft hese BODIPYs under hydrogenolytic conditions (necessary to deprotect benzylg roups at the glycosylu nits), the hydroxyethyl derivative 10 [35] was also considered as an on-benzylic analogue of 8.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

BODIPYs as Chemically Stable Fluorescent Tags for Synthetic Glycosylation Strategies towards Fluorescently Labeled Saccharides

Uriel

Permingeat

Ventura

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

As eries of fluorescent boron-dipyrromethene (BODIPY,4,,4a-diaza-s-indacene)d yes have been designed to participate, as aglycons, in synthetic oligosaccharide protocols. As such, they served ad ual purpose:f irst, by being incorporated at the beginning of the process( at the reducing-endof the growing saccharide moiety), they can function as fluorescent glycosyl tags, facilitating the detection and purification of the desired glycosidic intermediates,a nd secondly,t he presence of these chromophores on the ensuing compounds grants access to fluorescently labeled saccharides. In this context, as ought-after feature of the fluorescent dyes has been their chemical robustness. Accordingly, some BODIPY derivatives described in this work can withstand the reactionc onditions commonly employed in the chemical synthesiso fs accharides;n amely, glycosylation and protecting-group manipulations. Regarding their photophysical properties,t he BODIPY-labeled saccharides obtained in this work display remarkable fluorescence efficiency in water,r eaching quantum yield values up to 82 %, as well as notable lasing efficienciesa nd photostabilities.[a] Dr.

show abstract

Section: Bodipysand Glycosylation Reactionsmentioning

confidence: 66%

Section: Resultsmentioning

confidence: 99%

BODIPYs as Chemically Stable Fluorescent Tags for Synthetic Glycosylation Strategies towards Fluorescently Labeled Saccharides

Uriel

Permingeat

Ventura

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…There are many reports concerning the derivatization of the N 2bidentate dipyrrins by attaching a variety of substituents, extending the -planar dipyrrin nucleus, and introducing a nitrogen atom into the dipyrrin framework, then preparing the corresponding boron complexes. 16,31,32 These chemical modifications effectively tune the photophysical properties of the N 2 BODIPYs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

Chiba¹,

Nakamura²,

Matsuoka³

et al. 2020

Synlett

View full text Add to dashboard Cite

The dipyrrin–metal complexes and especially the boron complex 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) have recently attracted considerable attention because of their interesting properties and possible applications. We have developed two unique and useful ways to extend versatility and usefulness of the dipyrrin complexes. The first one is the linear and macrocyclic oligomerization of the BODIPY units. These arrangements of the B–F moieties of the oligomerized BODIPY units provide sophisticated functions, such as unique recognition ability toward cationic guest, associated with changes in the photophysical properties by utilizing unprecedented interactions between the B–F and a cationic species. The second one is introduction of additional ligating moieties into the dipyrrin skeleton. The multidentate N2Ox dipyrrin ligands thus obtained form a variety of complexes with 13 and 14 group elements, which are difficult to synthesize using the original N2 dipyrrin derivatives. Interestingly, these unique complexes exhibit novel structures, properties, and functions such as guest recognition, stimuli-responsive structural conversion, switching of the optical properties, excellent stability of the neutral radicals, etc. We believe that these multifunctional dipyrrin complexes will advance the basic chemistry of the dipyrrin complexes and develop their applications in the materials and medicinal chemistry fields.1 Introduction2 Linear Oligomers of Boron–Dipyrrin Complexes3 Cyclic Oligomers of Boron–Dipyrrin Complexes4 A Cyclic Oligomer of Zinc–Dipyrrin Complexes5 Group 13 Element Complexes of N2Ox Dipyrrins6 Chiral N2 and N2Ox Dipyrrin Complexes7 Group 14 Element Complexes of N2O2 Dipyrrins8 Other N2O2 Dipyrrin Complexes with Unique Properties and Functions9 Conclusion

show abstract

“…In this regard, both boron dipyrromethene dyes (BODIPYs) [16] and coumarins [17] are in themselves two of the more widely used fluorophores (Figure 1), and hence have optimal candidates to design multichromophore ongoing energy transfer processes. Indeed, the former luminophores stand out due to their stability, chemical versatility and tunable photophysical signatures [18,19], whereas the latter fluorophores can be also deeply functionalized and display spectral bands at higher energies than the BODIPY core. Thus, both chromophores are complementary from a spectral point of view, and hence are suitable building blocks to be combined in a single molecular structure towards the promotion of intramolecular energy transfer hops.…”

Section: Introductionmentioning

confidence: 99%

Ready Access to Molecular Rotors Based on Boron Dipyrromethene Dyes-Coumarin Dyads Featuring Broadband Absorption

et al. 2020

View full text Add to dashboard Cite

Herein we report on a straightforward access method for boron dipyrromethene dyes (BODIPYs)-coumarin hybrids linked through their respective 8- and 6- positions, with wide functionalization of the coumarin fragment, using salicylaldehyde as a versatile building block. The computationally-assisted photophysical study unveils broadband absorption upon proper functionalization of the coumarin, as well as the key role of the conformational freedom of the coumarin appended at the meso position of the BODIPY. Such free motion almost suppresses the fluorescence signal, but enables us to apply these dyads as molecular rotors to monitor the surrounding microviscosity.

show abstract

Synthesis of BODIPY dyes through postfunctionalization of the boron dipyrromethene core

Cited by 266 publications

References 551 publications

BODIPYs as Chemically Stable Fluorescent Tags for Synthetic Glycosylation Strategies towards Fluorescently Labeled Saccharides

BODIPYs as Chemically Stable Fluorescent Tags for Synthetic Glycosylation Strategies towards Fluorescently Labeled Saccharides

Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

Ready Access to Molecular Rotors Based on Boron Dipyrromethene Dyes-Coumarin Dyads Featuring Broadband Absorption

Contact Info

Product

Resources

About