<i>o</i>-Carborane-based fluorophores as efficient luminescent systems both as solids and as water-dispersible nanoparticles

Sinha, Sohini; Kelemen, Zsolt; Humpfner, Evelyn; Ratera, Imma; Malval, Jean‐Pierre; Jurado, José P.; Viñas, Clara; Teixidor, Francesc; Núñez, Rosario

doi:10.1039/d1cc07211k

Cited by 18 publications

(10 citation statements)

References 51 publications

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“…Recently, organic nanoparticles (ONPs) [ 28 ] and radical‐based ONPs have been proposed as fluorescence probes for in vitro bioimaging. [ 29 ] Indeed, polyhalogenated trityl radicals can achieve long‐wavelength emission without the need of an extended conjugated system.…”

Section: Introductionmentioning

confidence: 99%

“…The simplest strategy, in order to have a dual emission, is to bind together two different emitting species with different thermal quenching of the emission, or exploit different states of aggregation of the same fluorophore, like in the case of excimers. [12,15,24,26,27] Recently, organic nanoparticles (ONPs) [28] and radicalbased ONPs have been proposed as fluorescence probes for in vitro bioimaging. [29] Indeed, polyhalogenated trityl radicals can achieve long-wavelength emission without the need of an extended conjugated system.…”

Section: Introductionmentioning

confidence: 99%

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Ratiometric Nanothermometer Based on a Radical Excimer for In Vivo Sensing

Blasi

Gonzalez‐Pato

Rodrı́guez

et al. 2023

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Ratiometric fluorescent nanothermometers with near‐infrared emission play an important role in in vivo sensing since they can be used as intracellular thermal sensing probes with high spatial resolution and high sensitivity, to investigate cellular functions of interest in diagnosis and therapy, where current approaches are not effective. Herein, the temperature‐dependent fluorescence of organic nanoparticles is designed, synthesized, and studied based on the dual emission, generated by monomer and excimer species, of the tris(2,4,6‐trichlorophenyl)methyl radical (TTM) doping organic nanoparticles (TTMd‐ONPs), made of optically neutral tris(2,4,6‐trichlorophenyl)methane (TTM‐αH), acting as a matrix. The excimer emission intensity of TTMd‐ONPs decreases with increasing temperatures whereas the monomer emission is almost independent and can be used as an internal reference. TTMd‐ONPs show a great temperature sensitivity (3.4% K−1 at 328 K) and a wide temperature response at ambient conditions with excellent reversibility and high colloidal stability. In addition, TTMd‐ONPs are not cytotoxic and their ratiometric outputs are unaffected by changes in the environment. Individual TTMd‐ONPs are able to sense temperature changes at the nano‐microscale. In vivo thermometry experiments in Caenorhabditis elegans (C. elegans) worms show that TTMd‐ONPs can locally monitor internal body temperature changes with spatio‐temporal resolution and high sensitivity, offering multiple applications in the biological nanothermometry field.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ratiometric Nanothermometer Based on a Radical Excimer for In Vivo Sensing

Blasi

Gonzalez‐Pato

Rodrı́guez

et al. 2023

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“…For developing polymeric-carrier-coated theranostic modalities, efforts were made for therapy along with MRI imaging, , the use of [ 18 F]FBPA for PET, with polymer-coated magnetic nanoparticles along with hyperthemia antigen-targeting polymeric formulations for PET, and PEGylated Au NPs for SPECT imaging were reported . Additionally, BNCT in combination with fluorescent molecules or luminescent nanoformulations has also been explored. − These systems exhibited theranostic applications, but continuous imaging in vivo for observing a progress of drug interaction and therapy may not be possible in the absence of an external source for excitation. Although, very recently ZnGa 2 O 4 :Cr 3+ ,Sn 4+ -based PLNPs have been explored for theranostic applications as NIR imaging and doxorubicin delivery to treat glyomas, their applications for BNCT have not been explored to the best of authors’ knowledge.…”

Section: Introductionmentioning

confidence: 99%

Multimodal Applications of Zinc Gallate-Based Persistent Luminescent Nanoparticles in Cancer Treatment: Tumor Margining, Diagnosis, and Boron Neutron Capture Therapy

Sharma

Phapale

et al. 2022

ACS Appl. Bio Mater.

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On the basis of the boron neutron capture therapy (BNCT) modality, we have designed and synthesized a zinc gallate (ZnGa2O4)-based nanoformulation for developing an innovative theranostic approach for cancer treatment. Initially, the (ZnGa1.995Cr0.005O4 or ZnGa2O4:(0.5%)Cr persistent luminescence nanoparticles (PLNPs) embedded on silica matrix were synthesized. Their surface functionalization was performed using organic synthesis strategies to attach the amine functional moieties which were further coupled with poly(vicinal diol). These diols were helpful for conjugation with 10B(OH)3, which subsequently served to couple with an in-house-synthesized variant of pH-(low)-insertion peptide (pHLIP) finally giving a tumor-targeting nanoformulation. Most importantly, the polymeric diols helped in conjugation of a substantial number of 10B to provide the therapeutic dose required for effective BNCT. This nanoformulation internalized substantially (∼80%) to WEHI-164 cancer cells within 6 h. Tumor homing studies indicated that the accumulation of this formulation at the acidic tumor site was within 2 h. The in vitro evaluation of the formulation against WEHI-164 cancer cells followed by neutron irradiation revealed its potent cytotoxicity with IC50 ∼ 25 μM. In the case of studies on animal models, the melanoma-induced C57BL/6 and fibrosarcoma-induced BALB/c mice were treated with formulations through intratumoral and intravenous injections, respectively, followed by neutron irradiation, leading to a significant killing of the cancer cells, which was evidenced by a reduction in tumor volume (75–80%) as compared with a control tumor. Furthermore, the histopathological studies confirmed a damaging effect only on tumor cells, while there was no sign of damage to the vital organs in treated mice as well as in controls.

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“…In addition, the unencapsulated inverted PSC with the PDI-Cb interlayer has good photo-and thermal stability because it shows 9.3% efficiency degradation after continuous 1 sun light soaking for 1000 h at 85 °C in N 2 atmosphere. unique photophysical properties, [29][30][31][32][33][34] and use in optoelectronic applications, such as nonlinear optics (NLO), [35,36] solar cells, [37] and organic light-emitting diodes (OLEDs). [38,39] Here, diphenyl-o-carboranyl groups were introduced at the bay positions of the PDI unit, PDI-Cb, to investigate the synergistic effect of the PDI and o-Cb units.…”

Section: Introductionmentioning

confidence: 99%

“…[ 25,26 ] As a result, o‐Cb derivatives can act as an electron acceptor in the dyad system. Accordingly, o‐Cb derivatives have been investigated to study their electron‐accepting abilities, [ 27,28 ] unique photophysical properties, [ 29–34 ] and use in optoelectronic applications, such as nonlinear optics (NLO), [ 35,36 ] solar cells, [ 37 ] and organic light‐emitting diodes (OLEDs). [ 38,39 ]…”

Section: Introductionmentioning

confidence: 99%

Electron‐Accepting PDI–Cb Interlayer for over 22% Inverted Perovskite Solar Cells with Photo‐ and Thermal Stability

Heo

Lee

et al. 2022

Solar RRL

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To investigate the synergistic effect of perylene diimide (PDI) unit and diphenyl‐o‐carboranyl (Cb) group, PDI–Cb with Cb groups at the bay positions of the PDI unit is synthesized. By introducing 3D carboranyl group into the bay position, PDI–Cb shows distorted geometry between PDI core and the adjacent phenyl ring of Cb due to the ring torsions, which can suppress the aggregation tendency. Furthermore, the proper lowest unoccupied molecular orbital (LUMO) energy level of −4.12 eV may be beneficial to extract electrons from the perovskite efficiently. By introducing PDI–Cb interlayer at perovskite/C60 interface, the inverted perovskite solar cells (PSCs) have significantly enhanced efficiency from 19.98% to 22.31% at 1 sun condition (AM1.5G 100 mW cm−2) because the PDI–Cb interlayer promotes charge extraction thanks to the electron‐accepting ability of Cb group; thereby, it reduces carrier recombination significantly. In addition, the unencapsulated inverted PSC with the PDI–Cb interlayer has good photo‐ and thermal stability because it shows 9.3% efficiency degradation after continuous 1 sun light soaking for 1000 h at 85 °C in N2 atmosphere.

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o-Carborane-based fluorophores as efficient luminescent systems both as solids and as water-dispersible nanoparticles

Abstract: A set of o-carborane appended π-conjugated fluorophores and their light-emitting properties in solid state are reported. The aggregation-induced emission enhancement (AIEE) exhibited for one of the fluorenyl derivatives paved the...

Cited by 18 publications

References 51 publications

Ratiometric Nanothermometer Based on a Radical Excimer for In Vivo Sensing

Ratiometric Nanothermometer Based on a Radical Excimer for In Vivo Sensing

Multimodal Applications of Zinc Gallate-Based Persistent Luminescent Nanoparticles in Cancer Treatment: Tumor Margining, Diagnosis, and Boron Neutron Capture Therapy

Electron‐Accepting PDI–Cb Interlayer for over 22% Inverted Perovskite Solar Cells with Photo‐ and Thermal Stability

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