Photon‐Upconverting Ionic Liquids: Effective Triplet Energy Migration in Contiguous Ionic Chromophore Arrays

Hisamitsu, Shota; Yanai, Nobuhiro; Kimizuka, Nobuo

doi:10.1002/ange.201505168

Cited by 17 publications

(18 citation statements)

References 42 publications

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“…In this perspective, it is natural to develop triplet energy migration-based photon upconversion (TEM-UC), 10 in which triplet excitons effectively diffuse in densely organized molecular assemblies without molecular diffusion. [21][22][23][24][25][26][27][28][29][30][31][32] Among various assembly systems, molecular crystals with ordered chromophore arrangements should be promising for achieving fast TEM. However, the crystalline systems have suffered from the aggregation of donor molecules and their segregation in acceptor crystals, which caused poor TET efficiency.…”

Section: Introductionmentioning

confidence: 99%

Kinetically controlled crystal growth approach to enhance triplet energy migration-based photon upconversion

et al. 2017

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Nobuo Kimizuka, "Kinetically controlled crystal growth approach to enhance triplet energy migration-based photon upconversion," J. Photon. Energy 8(2), 022003 (2017), doi: 10.1117/1.JPE.8.022003. Abstract. Improving efficiency of triplet-triplet annihilation-based photon upconversion (TTA-UC) in crystalline media is challenging because it usually suffers from the severe aggregation of the donor (sensitizer) molecules in acceptor (emitter) crystals. We show a kinetically controlled crystal growth approach to improve donor dispersibility in acceptor crystals. As the donor-acceptor combination, a benchmark pair of platinum(II) octaethylporphyrin (PtOEP) and 9,10-diphenylanthracene (DPA) is employed. A surfactant-assisted reprecipitation technique is employed, where the concentration of the injected PtOEP-DPA solution holds the key to control dispersibility; at a higher PtOEP-DPA concentration, a rapid crystal growth results in better dispersibility of PtOEP molecules in DPA crystals. The improvement of donor dispersibility significantly enhances the TTA-UC quantum yield. Thus, the inherent function of donor-doped acceptor crystals can be maximized by controlling the crystallization kinetics.

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Section: Introductionmentioning

confidence: 99%

Kinetically controlled crystal growth approach to enhance triplet energy migration-based photon upconversion

et al. 2017

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“…Finally, this singlet excited state returns to the ground state by fluorescent emission of a high-energy photon, thereby realizing upconversion. TTA-UC has been demonstrated in various organic, inorganic, and/or supramolecular materials [15,[18][19][20][21][22], as well as in nano-or micro-sized particles [23][24][25]. For biological applications, i.e., for drug delivery and activation [26,27] or bio-imaging [13,[28][29][30][31][32][33], one of the main problems of TTA-UC is its sensitivity to molecular oxygen, which readily quenches the triplet state chromophores involved in the TTA-UC mechanism.…”

Section: Introductionmentioning

confidence: 99%

Red Light Activation of Ru(II) Polypyridyl Prodrugs via Triplet-Triplet Annihilation Upconversion: Feasibility in Air and through Meat

et al. 2016

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Triplet-triplet annihilation upconversion (TTA-UC) is a promising photophysical tool to shift the activation wavelength of photopharmacological compounds to the red or near-infrared wavelength domain, in which light penetrates human tissue optimally. However, TTA-UC is sensitive to dioxygen, which quenches the triplet states needed for upconversion. Here, we demonstrate not only that the sensitivity of TTA-UC liposomes to dioxygen can be circumvented by adding antioxidants, but also that this strategy is compatible with the activation of ruthenium-based chemotherapeutic compounds. First, red-to-blue upconverting liposomes were functionalized with a blue-light sensitive, membrane-anchored ruthenium polypyridyl complex, and put in solution in presence of a cocktail of antioxidants composed of ascorbic acid and glutathione. Upon red light irradiation with a medical grade 630 nm PDT laser, enough blue light was produced by TTA-UC liposomes under air to efficiently trigger full activation of the Ru-based prodrug. Then, the blue light generated by TTA-UC liposomes under red light irradiation (630 nm, 0.57 W/cm 2 ) through different thicknesses of pork or chicken meat was measured, showing that TTA-UC still occurred even beyond 10 mm of biological tissue. Overall, the rate of activation of the ruthenium compound in TTA-UC liposomes using either blue or red light (1.6 W/cm 2 ) through 7 mm of pork fillet were found comparable, but the blue light caused significant tissue damage, whereas red light did not. Finally, full activation of the ruthenium prodrug in TTA-UC liposomes was obtained under red light irradiation through 7 mm of pork fillet, thereby underlining the in vivo applicability of the activation-by-upconversion strategy.

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“…AIE materials such as (2Z,2'Z)-2,2'-(1,4-phenylene)bis(3-phenylacrylonitrile) and 9,10-distyrylanthracene (DSA) have been used as emitters in TTA-UC systems. [24,25] Given that DPA is an ideal emitter for TTA-UC, [5,[26][27][28] we thus determined whether the TPE-DPA derivatives could be used as emitters for solid-state TTA-UC.…”

Section: Tta-uc Studymentioning

confidence: 99%

Tetraphenylethene 9,10‐Diphenylanthracene Derivatives – Synthesis and Photophysical Properties

et al. 2019

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A series of tetraphenylethene 9,10‐diphenylanthracene (TPE‐DPA) derivatives have been synthesized, and their photophysical properties studied. Photoluminescence measurements in PMMA, neat films and nanoparticle dispersions reveal that different aggregation states are formed, which leads to different photophysical behavior. The triplet excited state properties were studied using Pt(II) octaethylporphyrin (PtOEP) as triplet sensitizer. Upconverted emission from the DPA moiety is observed in nanoparticle dispersions of each derivative. A higher upconverted emission intensity is observed in aerated (compared to deaerated) solutions of the derivatives following irradiation, which is attributed to oxidation of the TPE moiety. These results provide valuable insight for the design of AIE luminogens for triplet‐triplet annihilation upconversion (TTA‐UC).

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Photon‐Upconverting Ionic Liquids: Effective Triplet Energy Migration in Contiguous Ionic Chromophore Arrays

Cited by 17 publications

References 42 publications

Kinetically controlled crystal growth approach to enhance triplet energy migration-based photon upconversion

Kinetically controlled crystal growth approach to enhance triplet energy migration-based photon upconversion

Red Light Activation of Ru(II) Polypyridyl Prodrugs via Triplet-Triplet Annihilation Upconversion: Feasibility in Air and through Meat

Tetraphenylethene 9,10‐Diphenylanthracene Derivatives – Synthesis and Photophysical Properties

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