Redox-Active Metallacarborane-Decorated Octasilsesquioxanes. Electrochemical and Thermal Properties

Cabrera‐González, Justo; Arderiu, Víctor Sánchez; Viñas, Clara; Parella, Teodor; Teixidor, Francesç; Núñez, Rosario

doi:10.1021/acs.inorgchem.6b02394

Cited by 37 publications

(52 citation statements)

References 50 publications

(80 reference statements)

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“…The olefin resonances appear in the range d = 67.6-73.2 ppm, and for 7 and 8 the signals of C c -H appear at d = 46.4 and 54.5 ppm. MALDI-TOF mass spectra were recorded in negative-ionm ode for compounds 7 and 8, which showed the molecular ion peak with the boron isotopic distribution.H owever,a sh as been observed previously, [34] it was not possible to obtain MALDI-TOF mass spectra for 5 and 6.…”

Section: Synthesis and Spectroscopic Characterizationmentioning

confidence: 76%

“…Both series give rise to characteristicr esonances of pentacoordinated tin atoms. MALDI-TOF mass spectra were recorded in negative-ionm ode for compounds 7 and 8, which showed the molecular ion peak with the boron isotopic distribution.H owever,a sh as been observed previously, [34] it was not possible to obtain MALDI-TOF mass spectra for 5 and 6. [67][68][69] The 119 Sn shifts of all of the tin compounds are similart ot hose of recently reportedp entacoordinate diorganotin compoundsb earing hydroxybenzoylhydrazone moieties.…”

Section: Synthesis and Spectroscopic Characterizationmentioning

confidence: 84%

“…],r espectively,u nder similar conditions as previously describedf or an ucleophilico xonium ring-opening reaction [34] (Scheme 4). K 2 CO 3 was used as the base ford eprotonation of the -OH group in compounds 1 and 2;t he deprotonated species then act as nucleophilest oi nduce oxoniumr ing-opening.…”

Section: Synthesis and Spectroscopic Characterizationmentioning

confidence: 93%

“…Finally,b oron-rich molecules 5/ 6 and 7/8 weres ynthesized by one-pot reactions with [Bu 4 )],r espectively,u nder similar conditions as previously describedf or an ucleophilico xonium ring-opening reaction [34] (Scheme 4). These compounds were obtaineda sy ellow and orange crystalline solidsi n8 5% and 82 %y ields, respectively.C ompounds 3 and 4 were obtained as oils by the reactions of 1 and 2 with NaHCO 3 and 1bromododecane in acetonitrile.…”

Section: Synthesis and Spectroscopic Characterizationmentioning

confidence: 99%

“…[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%

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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: Synthesis and Spectroscopic Characterizationmentioning

confidence: 76%

Section: Synthesis and Spectroscopic Characterizationmentioning

confidence: 84%

Section: Synthesis and Spectroscopic Characterizationmentioning

confidence: 93%

Section: Synthesis and Spectroscopic Characterizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

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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Tetraphenylethylene–Carborane–Tetraphenylethylene Triad: Influence of Steric Bridge on Aggregation‐Induced Emission Properties

Yin

Yan

et al. 2018

Chemistry An Asian Journal

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A novel tetraphenylethylene (TPE)-bridge-tetraphenylethylene triad has been synthesized, where the o-carboranyl moiety functions as a central bridge and two TPE units are in the lateral positions. This molecular triad has been characterized by various spectroscopic methods, and its structure has been studied by X-ray crystallography as well as theoretical calculations. The impact of the bridging carboranyl unit on the aggregation-induced emission (AIE) characteristics of the TPE-bridge-TPE triad has been investigated. When the central bridge is changed from one-dimensional (1D) alkynyl to three-dimensional (3D) carboranyl, the absolute luminescent quantum yield of the triad increased from 21.2 % to 54.7 % in the solid state, accompanied by a luminescence color change from blue to yellow (94 nm red-shift).

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Geometric structural insights for enhanced radiative efficiency: Spiro[fluorene–carbazole]‐based ortho‐carboranyl luminophores

Ryu

Lee

Kim

et al. 2022

Bulletin Korean Chem Soc

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We herein report the preparation of two compounds (C1 and C2) with an ortho-carborane cage appended at the C4-position of the fluorene (C1) or carbazole (C2) moiety of their spiro[fluorene-carbazole] scaffolds. Photoluminescence spectra of both compounds in solution at 298 K did not demonstrate any emissive trace; however, those of both compounds in solution at 77 K and in the film state exhibited strong orange emission. Interestingly, the quantum efficiency and radiative decay constant of C2 in the film state were much higher than that of C1. This distinctly showed that the position of the ocarborane unit on the scaffold strongly affected the efficiency of the radiative decay process based on intramolecular charge transfer (ICT) transitions. These findings revealed that that the electronic environment of the scaffold-molecule linked with the o-carborane cage plays an important role to control the ICTbased radiative decay process.

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Redox-Active Metallacarborane-Decorated Octasilsesquioxanes. Electrochemical and Thermal Properties

Cited by 37 publications

References 50 publications

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

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

Tetraphenylethylene–Carborane–Tetraphenylethylene Triad: Influence of Steric Bridge on Aggregation‐Induced Emission Properties

Geometric structural insights for enhanced radiative efficiency: Spiro[fluorene–carbazole]‐based ortho‐carboranyl luminophores

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