Abstract:A small library of carborane-BODIPY/aza-BODIPY dyads were efficiently synthesized by means of a novel convergent synthetic approach, the key step of which is a Pd-catalyzed Heck coupling reaction. The structural characterization and photoluminescence properties of the newly synthesized dyads were evaluated. The presence of the carborane did not significantly alter the photophysical patterns of the BODIPY or aza-BODIPY in the final fluorophores, but it produced a decrease of the emission fluorescent quantum yie… Show more
“…[19][20][21] . Owing to the intrinsic properties of carboranes, they have been used as exceptional building blocks for developing functional organic materials with enhanced thermal and chemical properties 22-25 . In the last decade, the development of boron cluster-based organic -conjugated systems have attracted huge interest as active materials in (opto)electronic devices, such as organic lightemitting diodes (OLEDs), organic field effect transistors (OFETs), solar cells, biological sensors and imaging, [26][27][28] among others. 29,30 It has been demonstrated the remarkable influence of the o-carborane cluster on the photophysical properties of luminescent materials in solution and solid state.…”
m-Carborane has demonstrated to be a perfect platform to boost the fluorescence properties of anthracene, giving rise to high fluorescence quantum yields in solution and also retaining fluorescence emission in the aggregate state.
“…[19][20][21] . Owing to the intrinsic properties of carboranes, they have been used as exceptional building blocks for developing functional organic materials with enhanced thermal and chemical properties 22-25 . In the last decade, the development of boron cluster-based organic -conjugated systems have attracted huge interest as active materials in (opto)electronic devices, such as organic lightemitting diodes (OLEDs), organic field effect transistors (OFETs), solar cells, biological sensors and imaging, [26][27][28] among others. 29,30 It has been demonstrated the remarkable influence of the o-carborane cluster on the photophysical properties of luminescent materials in solution and solid state.…”
m-Carborane has demonstrated to be a perfect platform to boost the fluorescence properties of anthracene, giving rise to high fluorescence quantum yields in solution and also retaining fluorescence emission in the aggregate state.
“…Recently, we have reported that carborane-BODIPY dyads were easily internalized by HeLa cells, those bearing m-carborane clusters being the ones that show the best fluorescence characteristics for cell imaging purposes. 26 Owing to our interest to use fluorescent carborane derivatives for biological purposes, herein we have analysed the cytotoxicity and the potential use of compounds 4-6 as fluorescent probes for biological systems.…”
Section: Biological Assaysmentioning
confidence: 99%
“…Compounds 4-6 were dissolved and filtered following the same protocol as that in a previous work, 26 obtaining a final compound concentration of 10 µM and 0.5% of DMSO (Sigma/ Aldrich). 26 HeLa cells, which were routinely cultured under standard conditions, were used to analyse the cytotoxicity, the cellular uptake and the internalization pathway. 26,27…”
Section: Biological Assaysmentioning
confidence: 99%
“…26 HeLa cells, which were routinely cultured under standard conditions, were used to analyse the cytotoxicity, the cellular uptake and the internalization pathway. 26,27…”
Linking m-carborane to the anthracene dye produces an exceptional enhancement of the fluorescence properties, with quantum efficiencies close to 100% in solution. Dyads were internalized by HeLa cells through endocytosis showing intense blue emission.
“…The interest in carboranes and metallacarboranes as potential units for molecular materials might be endorsed to their remarkable chemical, thermal, and biological stabilities [7][8][9][10][11][12][13][14][15][16][17]. Owing to the properties above of carboranes, they have been used as exceptional building blocks for developing a large variety of fluorescent carborane-containing molecules, in which the cluster is usually linked to a fluorescent π-conjugated organic system, either directly by the C c [18][19][20][21][22][23][24][25][26][27][28][29][30] or through one spacer [7][8][9][31][32][33][34][35][36][37][38][39].…”
High boron content systems were prepared by the peripheral functionalisation of 1,3,5-triphenylbenzene (TPB) and octavinylsilsesquioxane (OVS) with two different anionic boron clusters: closo-dodecaborate (B12) and cobaltabisdicarbollide (COSAN). TPB was successfully decorated with three cluster units by an oxonium ring-opening reaction, while OVS was bonded to eight clusters by catalysed metathesis cross-coupling. The resulting compounds were spectroscopically characterised, and their solution-state photophysical properties analysed. For TPB, the presence of COSAN dramatically quenches the fluorescence emission (λem = 369 nm; ΦF = 0.8%), while B12-substituted TPB shows an appreciable emission efficiency (λem = 394 nm; ΦF = 12.8%). For octasilsesquioxanes, the presence of either COSAN or B12 seems to be responsible for ∼80 nm bathochromic shift with respect to the core emission, but both cases show low emission fluorescence (ΦF = 1.4–1.8%). In addition, a remarkable improvement of the thermal stability of OVS was observed after its functionalisation with these boron clusters.
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