Highly Dispersible and Stable Anionic Boron Cluster–Graphene Oxide Nanohybrids

Cabrera‐González, Justo; Cabana, Laura; Ballesteros, Belén; Tobias, Gerard; Núñez, Rosario

doi:10.1002/chem.201505044

Cited by 19 publications

(17 citation statements)

References 43 publications

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“…[28,29] COSANh as ad ispersed negative charget hat gives rise to electrostatic interactions, [30] and ah ydrophobic surface that can engagei nn onbondingi ntermolecular interactions through its weakly polarized BÀHa nd CÀHb onds. [31,32] These inorganic anions have been shown to possesse xceptional chemicala nd thermals tability, [33][34][35] amphiphilicity, [36][37][38][39][40][41][42] as well as unusual physicochemical properties in water that confer an ability to self-assemble into micelles and monolayer vesicles. [36,41,43] The visualization of lipidic membranes by COSAN-containingf luoresceinp robes has also been reported.…”

Section: Introductionmentioning

confidence: 99%

Organotin Dyes Bearing Anionic Boron Clusters as Cell‐Staining Fluorescent Probes

Muñoz‐Flores

Cabrera‐González

Viñas

et al. 2018

Chemistry A European J

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Within the cell nucleus, in the nucleoli, ribosomal RNAs are synthesized and participate in several biological processes. To better understand nucleoli-related processes, their visualization is often required, for which specific markers are needed. Herein, we report the design of novel fluorescent organotin compounds derived from 4-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)benzohydrazide and their cytoplasm and nucleoli staining of B16F10 cells in vitro. Tin compounds bearing an aliphatic carbon chain (-C H ) and an electron-donating group (-OH) were prepared, and the latter could be derivatized to bear the boron cluster anions [B H ] and [3,3'-Co(1,2-C B H ) ] (COSAN). All of the conjugates have been fully characterized and their luminescence properties have been assessed. In general, they show good quantum yields in solution (24-49 %), those for the COSAN derivatives being lower. Remarkably, the linking of [B H ] and COSAN to the complexes made them more soluble, without being detrimental to their luminescence properties. Living B16F10 cells were treated with all of the compounds to determine their fluorescence staining properties; the compounds bearing the aliphatic chain showed a reduced staining capacity due to the formation of aggregates. Notably, the complexes bearing different boron clusters showed different staining effects; those bearing [B H ] showed extraordinary staining of the nucleoli and cytoplasm, whereas those bearing COSAN were only detected in the cytoplasm. The remarkable fluorescence staining properties shown by these organotin compounds make them excellent candidates for fluorescence bioimaging in vitro.

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Section: Introductionmentioning

confidence: 99%

Organotin Dyes Bearing Anionic Boron Clusters as Cell‐Staining Fluorescent Probes

Muñoz‐Flores

Cabrera‐González

Viñas

et al. 2018

Chemistry A European J

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“…Anionic metallacarboranes, in especial the well-known cobaltabisdicarbollide, usually called COSAN, [3,3'-Co-(C 2 B 9 H 11 ) 2 ] À , have demonstrated to have extraordinary chemical, thermal and photochemical stabilities. [12][13][14] COSAN is an hydrophobic species, [15,16] with low nucleophilic character, high molecular volume and low charge density. [17] The hydrophobic nature of COSAN provides to its protonated form and sodium salt exceptional amphiphilic character, making them soluble in water and organic solvents.…”

Section: Introductionmentioning

confidence: 99%

“…Anionic metallacarboranes, in especial the well‐known cobaltabisdicarbollide, usually called COSAN, [3,3’‐Co(C 2 B 9 H 11 ) 2 ] − , have demonstrated to have extraordinary chemical, thermal and photochemical stabilities [12–14] . COSAN is an hydrophobic species, [15,16] with low nucleophilic character, high molecular volume and low charge density [17] .…”

Section: Introductionmentioning

confidence: 99%

Far‐Red and Near‐Infrared Boron Schiff Bases (BOSCHIBAs) Dyes Bearing Anionic Boron Clusters

et al. 2021

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Here, we report a short series of six new boron Schiff bases (BOSCHIBAs), four of them bearing anionic boron clusters. The boron complexes (1-2) were synthesized by the multicomponent reaction. The Boron Schiff bases were appropriately functionalized with boron cluster anions [B 12 H 12 ] 2À (3-4) and [3,3'-Co(C 2 B 9 H 11 ) 2 ] À (5-6). Remarkably, BOSCHIBAs bearing [B 12 H 12 ] 2À showed fluorescence emission to the NIR and far-red regions (3: 747 nm, 4: 690 nm), while 5 and 6 exhibited emission in the UV region (5: 525 and 6: 475 nm). Notably, complexes 2, 5, and 6 showed the highest photostability, followed by the boron complexes 1 and 3, which suggest that the nature of the boron cluster influences photostability properties. Compounds 3-4 represent the first example of boron Schiff bases bearing boron cluster anions [B 12 H 12 ] 2À exhibiting fluorescence emission in the NIR and far-red regions, make them potential candidates as fluorescence probes for bioimaging.

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“…[11] The latter makes the protonated form and sodium salts of COSANh ighly amphiphilic, which accounts for their good solubility both in water and organic solvents, as well as for their capacity to self-assemble into micelles andm onolayer vesicles in aqueous media. [12] Because of this combination of properties, COSAN has been efficiently linked to the surface of platforms of different nature,s uch as dendrimers, [13] octasilsesquioxanes, [14] TiO 2 [15] and polymeric nanoparticles, [16] SWCNTs [17] or graphene oxide, [18] giving rise to materials with enhanced solubility,d ispersability,t hermals tability,a nd electrochemical features.…”

Section: Introductionmentioning

confidence: 99%

Reversibly Switchable Fluorescent Molecular Systems Based on Metallacarborane–Perylenediimide Conjugates

Parejo

Chaari

Santiago

et al. 2020

Chemistry A European J

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Icosahedral metallacarboranes are q-shaped anionic molecules in which two icosahedra share one vertex that is am etal center. The most remarkable of these compounds is the anionic cobalt-based metallacarborane [Co(C 2 B 9 H 11) 2 ] À , whose oxidation-reduction processes occur via an outer sphere electron process. This, along with its low density negative charge, makes[ Co(C 2 B 9 H 11) 2 ] À very appealingt o participatei ne lectron-transfer processes. In this work, [Co(C 2 B 9 H 11) 2 ] À is tethered to ap erylenediimided ye to produce the first examples of switchable luminescentm olecules and materials based on metallacarboranes. In particular, the electronic communication of [Co(C 2 B 9 H 11) 2 ] À with the appended chromophore unit in these compounds can be regulated upon application of redox stimuli, which allows the reversible modulation of the emitted fluorescence. As such, they behave as electrochemically-controlled fluorescent molecular switches in solution, which surpass the performance of previous systemsb ased on conjugates of perylendiimides with ferrocene. Remarkably,t hey can form gels by treatment with appropriate mixtureso fo rganic solvents, which result from the self-assembly of the cobaltabisdicarbollide-perylendiimidec onjugates into 1D nanostructures. The interplay between dye p-stackinga nd metallacarborane electronic and steric interactions ultimately governs the supramolecular arrangementi nt hese materials, which for one of the compoundsp repared allows preserving the luminescent behavior in the gel state.

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Highly Dispersible and Stable Anionic Boron Cluster–Graphene Oxide Nanohybrids

Cited by 19 publications

References 43 publications

Organotin Dyes Bearing Anionic Boron Clusters as Cell‐Staining Fluorescent Probes

Organotin Dyes Bearing Anionic Boron Clusters as Cell‐Staining Fluorescent Probes

Far‐Red and Near‐Infrared Boron Schiff Bases (BOSCHIBAs) Dyes Bearing Anionic Boron Clusters

Reversibly Switchable Fluorescent Molecular Systems Based on Metallacarborane–Perylenediimide Conjugates

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