Monitoring of the ADP/ATP Ratio by Induced Circularly Polarised Europium Luminescence

Shuvaev, Sergey; Fox, Mark A.; Parker, David

doi:10.1002/ange.201801248

Cited by 29 publications

(13 citation statements)

References 28 publications

(50 reference statements)

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“…The organic phase was dried by rotary evaporation followed with column chromatography (petroleum ether/ ethyl acetate = 10:1) purification to afford R/S-3 (3.88 g, 78%) as a white solid. 1 (20 mL) was added to the reaction. After stirring at room temperature overnight, hydrochloric acid (2.0 mol L −1 ) was used to neutralize the solution.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Circularly Polarized Electroluminescence of Thermally Activated Delayed Fluorescence-Active Chiral Binaphthyl-Based Luminogens

Wang¹,

Yu²,

Hu³

et al. 2019

ACS Appl. Mater. Interfaces

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Two pairs of thermally activated delayed fluorescence (TADF)active chiral luminogens (R/S-1 and R/S-2) can be achieved by introducing D− A-type groups to chiral BINOL skeletons. The resulting chiral luminogens can exhibit aggregation-induced emission properties in THF−water mixtures and TADF emission in a doped-film state. The absolute photoluminescence quantum yield (Φ PL ) and delayed fluorescence lifetimes (τ delayed ) were measured to be 18.5% and 1.03 μs for R-1 and 15.7% and 0.97 μs for R-2. However, only R/S-1 with the fixed conjugation structure can emit circularly polarized luminescence signals, and g lum can reach 1.6 × 10 −3 in toluene solution and 9.2 × 10 −4 in the neat film. Most importantly, R/S-1 was chosen as the emitting layers for orangered circularly polarized organic light-emitting diodes, which can display low turnon voltage (V on ) of 3.4 V, high maximum brightness (L max ) up to 40 470 cd m −2 , moderate external quantum efficiency of 4.1%, as well as circularly polarized electroluminescence signal with g EL = −0.9 × 10 −3 /+1.0 × 10 −3 .

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Circularly Polarized Electroluminescence of Thermally Activated Delayed Fluorescence-Active Chiral Binaphthyl-Based Luminogens

Wang¹,

Yu²,

Hu³

et al. 2019

ACS Appl. Mater. Interfaces

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“…Thanks to the first peculiarity, one can use time-gated detection to mitigate the interference of background fluorescence originating from the biological sample and hence to isolate the Ln(III) luminescence. This advantageous feature has been exploited, for example, to obtain a high signal-to-noise (S/N) ratio by means of Eu(III)-based probes in the detection of intracellular pH 7 as well as other important bioanalytes, such as bicarbonate, 8 , 9 citrate, 10 lactate, 11 ATP, 12 , 13 and vitamin C. 14 Based on the antenna effect, the luminescence intensity of the metal ion can be considerably enhanced if the ligand is capable of strongly absorbing and efficiently transferring the UV excitation to the Ln(III) center. At the same time, high values of the emission quantum yield are required.…”

Section: Introductionmentioning

confidence: 99%

Effect of the Heteroaromatic Antenna on the Binding of Chiral Eu(III) Complexes to Bovine Serum Albumin

et al. 2020

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The cationic enantiopure ( R,R ) and luminescent Eu(III) complex [Eu(b iso Qcd)(H 2 O) 2 ] OTf (with b iso Qcd = N,N′ -bis(2- iso quinolinmethyl)- trans -1,2-diaminocyclohexane N,N′ -diacetate and OTf = triflate) was synthesized and characterized. At physiological pH, the 1:1 [Eu(b iso Qcd)(H 2 O) 2 ] + species, possessing two water molecules in the inner coordination sphere, is largely dominant. The interaction with bovine serum albumin (BSA) was studied by means of several experimental techniques, such as luminescence spectroscopy, isothermal titration calorimetry (ITC), molecular docking (MD), and molecular dynamics simulations (MDS). In this direction, a ligand competition study was also performed by using three clinically established drugs (i.e., ibuprofen, warfarin, and digitoxin). The nature of this interaction is strongly affected by the type of the involved heteroaromatic antenna in the Eu(III) complexes. In fact, the presence of iso quinoline rings drives the corresponding complex toward the protein superficial area containing the tryptophan residue 134 (Trp134). As the main consequence, the metal center undergoes the loss of one water molecule upon interaction with the side chain of a glutamic acid residue. On the other hand, the similar complex containing pyridine rings ([Eu(bpcd)(H 2 O) 2 ]Cl with bpcd = N,N′ -bis(2-pyridylmethyl)-trans-1,2-diaminocyclohexane N,N′ -diacetate) interacts more weakly with the protein in a different superficial cavity, without losing the coordinated water molecules.

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“…As such, lanthanide-based receptors for anions can also behave as molecular sensors: gadolinium(III) complexes as relaxivity probes or responsive MRI contrast agents, , and terbium(III) and europium(III) analogues as luminescent ones . Given these advantages, many lanthanide complexes have been reported as probes for anions including phosphate, − carbonate, ,,− fluoride, − cyanide, , and carboxylates such as acetate, ,, lactate, ,, citrate, − oxalate, malonate, and salicylate …”

Section: Introductionmentioning

confidence: 99%

The Stability of the Complex and the Basicity of the Anion Impact the Selectivity and Affinity of Tripodal Gadolinium Complexes for Anions

et al. 2019

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The affinities and selectivities of lanthanide complexes with open coordination sites for anions vary considerably with the chelate. In order to determine the effect of the stability of a lanthanide complex on its affinity for anions, five different complexes featuring different bidentate chelating moieties were synthesized, and their affinity for anions in water at neutral pH were evaluated by longitudinal relaxometry measurements. The chelates comprise both oxygen and nitrogen donors including maltol, 1,2-hydroxypyridinone, hydroxamic acid, pyridin-2-ylmethanol, and carbamoylmethylphosphonate diester. They were chosen to span a range of basicities all the while maintaining a similar tripodal tris-bidentate architecture, thereby allowing for a direct study of the role of the coordinating motif on the supramolecular recognition of anions by the corresponding Gd III complex. Overall, for ligands containing the same number of protonation steps, and therefore the same charge at neutral pH, the lower the acidity of the chelate (higher ∑pK a 's), the less stable the corresponding Gd III complex, and the higher its affinity for anions. Regardless of the number of protonation steps, the more stable Gd III complexes form ternary or quaternary assemblies with coordinating anions. In contrast, the same anions readily displace the chelate of the least stable complexes, resulting instead in the formation of Gd III •anion precipitates. Irrespective of the chelate, in the absence of steric hindrance at the open coordination site, the affinity of Gd III complexes for anions follows the order phosphate > arsenate > bicarbonate > fluoride. Hence, the selectivity and affinity of Gd III complexes of tripodal tris-bidentate chelates for anions is a function of the stability of the Gd III complex and the basicity of the anion.

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Monitoring of the ADP/ATP Ratio by Induced Circularly Polarised Europium Luminescence

Cited by 29 publications

References 28 publications

Circularly Polarized Electroluminescence of Thermally Activated Delayed Fluorescence-Active Chiral Binaphthyl-Based Luminogens

Circularly Polarized Electroluminescence of Thermally Activated Delayed Fluorescence-Active Chiral Binaphthyl-Based Luminogens

Effect of the Heteroaromatic Antenna on the Binding of Chiral Eu(III) Complexes to Bovine Serum Albumin

The Stability of the Complex and the Basicity of the Anion Impact the Selectivity and Affinity of Tripodal Gadolinium Complexes for Anions

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