Luminescent Complexes Research Articles

A glycyrrhetinic acid-iridium(III) conjugate as a theranostic NIR probe for hepatocellular carcinoma with mitochondrial-targeting ability

Hepatocellular carcinoma (HCC) is a major contributor to global mortality rates, but current treatment options have limitations. Advanced theranostics are needed to effectively integrate diagnosis and therapeutic of HCC. Glycyrrhetinic acid (GA) has abundant binding sites with glycyrrhetinic acid receptors (GA-Rs) on the surface of HCC cells and has also been reported to possess ligands with mitochondrial-targeting capability but with limited efficacy. Herein, we report a near-infrared (NIR) luminescent theranostic complex 1 through conjugating an iridium(III) complex to GA, which exhibits the desired photophysical properties and promotes mitochondrial-targeting capability. Complex 1 was selectively taken up by HepG2 liver cancer cells and was imaged within mitochondria with NIR emission. Complex 1 targeted mitochondria and opened mitochondrial permeability transition pores (MPTPs), resulting in ROS accumulation, mitochondrial damage, disruption of Bax/Bcl-2 equilibrium, and tumor cell apoptosis, resulting in significantly improved anticancer activity compared to GA. This work offers a methodology for developing multifunctional theranostic probes with amplified specificity and efficacy.

Linkage of the Dinuclear Gold(I) Complex Luminescence and Origin of Endocyclic Amino Group of Cyclic P2N2-Bridging Ligands.

Gold(I) complexes of LAu2Cl2 composition based on P2N2 ligands, namely 1,5-diaza-3,7-diphosphacyclooctanes, containing ethylpyridyl substituents at the phosphorus atoms and sp2- or sp3-hybridized endocyclic nitrogen atoms were synthesized. The SCXRD analysis indicated the strong impact of the geometry of the nitrogen atom on the structure and conformational flexibility of the complexes. The N-aryl substituted ligand with the planar endocyclic nitrogen atom provides higher flexibility of the complex and an ability to bind the solvent molecules in the "host-guest" mode, whereas that kind of behavior is forbidden for the complex with an N-alkyl substituted ligand with a pyramidal nitrogen atom. The substituents at nitrogen atoms also control the origin of the emission, which is phosphorescence for the N-aryl substituted complex and fluorescence for the N-alkylaryl substituted complex. The phosphorescent gold(I) complex displays high cytotoxicity without selectivity toward the m-HeLa and normal cells, but the core-shell nanoparticles formed on the base of the complex demonstrate reduced cytotoxicity. The luminescence of the NPs allows tracking the complexes in the cell samples.

Two-Photon Circularly Polarized Luminescence of Chiral Eu Complexes.

We report the synthesis of chiral lanthanide complexes with extended π conjugation for efficient circularly polarized luminescence (CPL) via two-photon excitation (2PE). The pyridine bis-oxazoline (PyBox) core provides the chiral Ln3+ environment, while the extension of the conjugated backbone through the pyridine 4-position with a phenylacetylene unit increases the two-photon absorption cross section. This work presents an important step toward the development of chiral systems displaying enhanced nonlinear optical properties, with potential applications in imaging and sensing, as well as in photodynamic therapy due to the selective excitation of molecules within a specific focal volume.

Highly luminescent soft aggregates and films assembled by amphiphilic polyoxometalate complex in a polymerizable aprotic ionic liquid

Hybrid co-assembly from lanthanide-containing polyoxometalates (POMs) and surfactants could efficiently optimize the formed aggregate luminescent properties and structural diversity. Meanwhile, compared to conventional solvents, aprotic ionic liquids (ILs) are not only excellent assembly media but also ideal solvents for luminescent lanthanide compounds. Therefore, in this work, the luminescent amphiphilic POM complex, namely surfactant-encapsulated POM hybrid (SEP) was initially prepared mainly through electrostatic interaction from polyanionic lanthanide-containing POM, Na9(EuW10O36)·32H2O (EuW10) and cationic surfactant, 1-octadecyl-3-methylimidazolium bromide ([C18mim]Br, OB). Then, highly luminescent lamellar micro-fiber aggregates were assembled by SEP in a polymerizable imidazolium-IL solvent, i.e. 1-vinyl-3-butyl imidazolium terafluoroborate ([Vbim]BF4). After morphology and structure characterizations for soft aggregates in detail, a lamellar aggregation arrangement mechanism was proposed. Further through in situ photopolymerization for such aggregate matrices, the flexible and organized films with enhanced luminescent properties were obtained. Our work indicates that the rational design of polymerizable organized aggregate matrices in ILs could greatly improve the photophysical properties of such luminescent soft materials and also expand their practical applications.

Synthesis of iron oxide nanocubes and their incorporation with luminescent lanthanide (Ln = Tb/ Eu)-Terephthalate complex in silica nanospheres using a reverse microemulsion method

Luminescent magnetic nanocomposites are of interest because of their promising applications in the biomedical field. This article reports the preparation of silica-coated lanthanide terephthalate complexes, Ln-TA (Ln = Tb and Eu) containing luminescent magnetic nanocomposites. Cubic-shaped iron oxide nanoparticles were synthesized through the thermal decomposition of the iron-oleate complex. Then, polymerization of tetraethyl ortho silicate in a water-in-oil reverse microemulsion in the presence of previously prepared iron oxide nanocubes and a terbium (Tb3+)/europium (Eu3+)-terephthalate (TA) complex was performed to obtain luminescent magnetic Fe3O4@Ln-TA (Ln = Tb, Eu)/SiO2 nanocomposites. The size (8.9 nm) and cubic shape of magnetic core were determined via transmission electron microscopy and the superparamagnetic behavior using a vibrating sample magnetometer. Energy dispersive X-ray analysis and inductively coupled plasma optical emission spectroscopy found that the luminescent Tb-TA and Eu-TA complexes were incorporated in the magnetic silica nanocomposites. The nanocomposites, Fe3O4@Ln-TA/SiO2, exhibited distinct luminescent green and red emission peaks and showed promise as a T1 contrast agent for magnetic resonance imaging.

Targeted, Molecular Europium(III) Probes Enable Luminescence-Guided Surgery and 1 Photon Post-Surgical Luminescence Microscopy of Solid Tumors.

Discrete luminescent lanthanide complexes represent a potential alternative to organic chromophores due to their tunability of optical properties, insensitivity to photobleaching, and large pseudo-Stokes shifts. Previously, we demonstrated that the lack of depth penetration of UV excitation required to sensitize discrete terbium and europium complexes can be overcome using Cherenkov radiation emitted by clinically employed radioisotopes in situ. Here, we show that the second-generation europium complexes [Eu(III)(pcta-PEPA2)] and [Eu(III)(tacn-pic-PEPA2)] (Φ = 57% and 76%, respectively) lower the limit of detection (LoD) to 1 nmol in the presence of 10 μCi of Cherenkov emitting isotopes, 18F and 68Ga. Bifunctionalization provides access to cysteine-linked peptide conjugates with comparable brightness and LoD. The conjugate, [Eu(tacn-(pic-PSMA)-PEPA2)], displays high binding affinity to prostate-specific membrane antigen (PSMA)-expressing PC-3 prostate cancer cells in vitro and can be visualized in the membrane-bound state using confocal microscopy. Biodistribution studies with the [86Y][Y(III)(tacn-(pic-PSMA)-PEPA2)] analogue in a mouse xenograft model were employed to study pharmacokinetics. Systemic administration of the targeted Cherenkov emitter, [68Ga][Ga(III)(PSMA-617)], followed by intratumoral injection or topical application of 20 or 10 nmol [Eu(III)(tacn-(pic-PSMA)-PEPA2)], respectively, in live mice resulted in statistically significant signal enhancement using conventional small animal imaging (620 nm bandpass filter). Optical imaging informed successful tumor resection. Ex vivo imaging of the fixed tumor tissue with 1 and 2 photon excitation further reveals the accumulation of the administered Eu(III) complex in target tissues. This work represents a significant step toward the application of luminescent lanthanide complexes for optical imaging in a clinical setting.

Luminescent Platinum Complexes with π-Extended Aryl Acetylide Ligands Supported by Isocyanides or Acyclic Diaminocarbenes.

In this work, we present a series of luminescent platinum acetylide complexes with acetylides that are electronically modified and/or π-extended. Six isocyanide-supported complexes with the general formula cis-[Pt(CNAr)2(C≡CR)2] and six acyclic diaminocarbene (ADC) complexes of the form trans-[Pt(ADC)2(C≡CR)2], all using the same five acetylide ligands, are described. The compounds are characterized by multinuclear NMR, FT-IR, and single-crystal X-ray diffraction. In most cases, the phosphorescence arises from an acetylide-centered 3(π → π*) excited state, although in one of the isocyanide compounds there is evidence for a charge-transfer excited state. The photoluminescence wavelength depends strongly on the substitution pattern and extent of the π conjugation on the acetylide, with maxima spanning the range of ca. 460-540 nm. Most photoluminescence lifetimes are long, beyond 50 μs, and quantum yields are low to moderate, 0.043-0.27. The photoluminescence quantum yields and lifetimes in these compounds do not systematically improve in the ADC complexes compared to the isocyanide versions, suggesting the neutral ligand σ-donor character does not play a large role in the excited-state dynamics when the triplet excited state is delocalized over a large π system.

Construction of bifunctional CdII luminescent coordination complexes and efficient detection of Cr2O72− and 2,4,6-trinitrophenol

Three new CdII coordination polymers (CPs) based on a new flexible large π-electron-rich bis(pyridinyl-imidazole) ligand 9,10-bis((2-(pyridin-2-yl)-1H-imidazole-1-yl)methyl)anthracene (bpima) have been synthesized under solvothermal conditions using a mixed-ligand strategy: {[Cd(bpima)0.5(nda)(H2O)]·DMF} (CP 1), {[Cd(bpima)0.5(oba)]·DMF·2H2O} (CP 2), {[Cd(bpima)0.5(ipa)(H2O)]·DMF·2H2O} (CP 3), (H2nda = naphthalene-1,4-dicarboxylic acid; H2oba = 4,4′-oxydibenzoic acid and H2ipa = 5-(tert-butyl)isophthalic acid). CP 1 and CP 2 both feature 2D layer structures with hcb and sql topology, respectively. CP 3 shows 1D ladder-like double-chain structure. In additional, luminescent properties of CP 1 and CP 3 have been systematically investigated and demonstrated multi-responsive luminescent sensitivities. Two compounds can be used for detection of Cr2O72− and 2,4,6-trinitrophenol (TNP) with high sensitivity (High quenching efficiency Ksv: for Cr2O72−: 5.07 × 104 M−1 for CP 1 and 7.38 × 104 M−1 for CP 2; for TNP: 4.87 × 104 M−1 for CP 1 and 5.13 × 104 M−1 for CP 2. low detection limit values: for Cr2O72−: 0.56 μM for CP 1 and 0.38 μM for CP 2; for TNP: 0.63 μM for CP 1 and 0.52 μM for CP 2) and as well as good recyclability. In addition, the sensing mechanism for Cr2O72− and TNP is also discussed by experimental studies and theory calculations, which was attributed to the co-existence of competitive absorption (CA), fluorescence resonance energy transfer (FRET) and photoinduced electron transfer (PET) progress for TNP and CA progress for Cr2O72−, respectively. Moreover, simple fluorescent filter paper based on CP 1 has been developed to achieve detection of Cr2O72− and TNP via the unaided eye, which has great potential for practical applications.

Upconversion Luminescence in Mononuclear Yb/Sm Co‐crystal Assemblies at Room Temperature

AbstractMetal‐based upconversion luminescence transforming high‐energy photons into low‐energy photons is an attractive anti‐Stokes shift process for fundamental research and promising applications. In this work, we developed the upconversion luminescence in co‐crystal assemblies consisting of discrete mononuclear Yb and Sm complexes. The characteristic visible emissions of Sm3+ were observed under the excitation of absorption band of Yb3+ at 980 nm. A series of co‐crystal assemblies were investigated based on mononuclear Yb and Sm complexes, and the strongest luminescence was obtained when the molar concentration between Yb3+ and Sm3+ is equivalent. The crystal structure was fully characterized by the single crystal X‐ray diffraction and upconverting energy transfer mechanisms were verified as cooperative sensitization upconversion and energy transfer upconversion. This is the first example of Sm3+‐based upconverting luminescence in discrete lanthanide complexes which present as co‐crystal assemblies at room temperature.

Polarity-Tunable Luminescence and Intersystem Crossing of a Zinc(II) Diimine Dithiolate Complex.

Combined density functional theory and multireference configuration interaction methods including spin-orbit interactions have been employed to investigate the photophysical properties and deactivation pathways of a zinc diimine dithiolate complex involving the phenanthroline derivative bathocuproine and the dianionic dithiosquarate as chelating ligands. Zn(batho)(dtsq) is one of the few luminescent zinc complexes for which triplet emission had been reported in the solid state [Gronlund, P. Inorg. Chim. Acta 1995, 234, 13-18]. Because of the high dipole moment of the complex in the electronic ground state, ligand-to-ligand charge-transfer (LLCT) states experience strong hypsochromic shifts in polar media, while ligand-centered (LC) states are nearly unaffected. Rate constants for the thermally activated upconversion of the TLLCT population to the SLLCT state are promising due to a small singlet-triplet energy gap and the participation of the sulfur in the electronic excitation, but the TLLCT state is not the lowest-lying excited triplet state in ethanol solution. In addition to the TLLCT electronic structure, TLC(batho)' and TLC(dtsq) ππ* excitations form minima on the T1 potential energy surface. The SLLCT luminescence is expected to be quenched at the nanosecond time scale by the dark TLC(dtsq)ππ* state. Moreover, a TLC(dtsq)σπ* state has been identified, which leads to degradation of the compound. In mildly polar media, the dark triplet LC states are energetically inaccessible and the lowest excited singlet and triplet states clearly exhibit an LLCT character. However, their mutual spin-orbit coupling is reduced to the extent that reverse intersystem crossing is not very likely at room temperature. While Zn(diimine)(dithiolate) complexes continue to be perceived as an interesting substance class with potential application as emitters in electroluminescent devices, the particular Zn(batho)(dtsq) complex is not considered suitable for that purpose.

Multiple Triplet Metal-Centered Jahn-Teller Isomers Determine Temperature-Dependent Luminescence Lifetimes in [Ru(bpy)3 ]2.

Understanding the factors that determine the luminescence lifetime of transition metal compounds is key for applications in photocatalysis and photodynamic therapy. Here we show that for (bpy = 2,2'-bipyridine), the generally accepted idea that emission lifetimes can be controlled optimizing the energy barrier from the emissive triplet metal-to-ligand charge-transfer (3 MLCT) state to the thermally-activated triplet metal-centered (3 MC) state or the energy gap between both states is a misconception. Further, we demonstrate that considering a single relaxation pathway determined from the minimum that is lowest in energy leads to wrong temperature-dependent emission lifetimes predictions. Instead, we obtain excellent agreement with experimental temperature-dependent lifetimes when an extended kinetic model that includes all the pathways related to multiple Jahn-Teller isomers and their effective reaction barriers is employed. These concepts are essential to correctly design other luminescent transition metal complexes with tailored emission lifetimes based on theoretical predictions.

Mehrere Triplett-Metall-zentrierte Jahn-Teller-Isomere bestimmen die temperaturabhängigen Lumineszenzlebensdauern in [Ru(bpy)3]2.

AbstractEin genaues Verständnis der Faktoren, welche die Lumineszenzlebensdauer von Übergangsmetallverbindungen bestimmen, ist für Anwendungen in der Photokatalyse und der photodynamischen Therapie von entscheidender Bedeutung. Die im Falle von [Ru(bpy)3]2+ (bpy=2,2’‐Bipyridin) allgemein akzeptierte Theorie besagt, dass die Emissionslebensdauer durch Optimierung der Energiebarriere zwischen dem emittierenden Triplett‐Zustand des Metall‐Liganden‐Ladungstransfers (3MLCT) und dem thermisch aktivierten Triplett‐Zustand des Metall‐Zentrums (3MC), oder der Energielücke zwischen beiden Zuständen gesteuert werden kann. Hier zeigen wir, dass dies nicht allgemeingültig ist. Darüber hinaus demonstrieren wir, dass die Betrachtung eines einzelnen Relaxationspfades, der vom energetisch niedrigsten Minimum aus bestimmt wird, zu falschen Vorhersagen der temperaturabhängigen Emissionslebensdauer führt. Stattdessen erhalten wir eine ausgezeichnete Übereinstimmung mit den experimentellen temperaturabhängigen Lebensdauern, wenn ein erweitertes kinetisches Modell herangezogen wird, welches alle Pfade im Zusammenhang mit mehreren Jahn–Teller‐Isomeren und ihren effektiven Reaktionsbarrieren beinhaltet. Diese Konzepte sind für das Design weiterer lumineszierender Übergangsmetallkomplexe mit individuell angepassten Emissionslebensdauern auf der Grundlage theoretischer Vorhersagen unerlässlich.

Europium(III) and gallic acid ligand coordination compounds: synthesis, characterization, photophysical processes, and optimization of luminescent properties

We obtained EuIII, GdIII, and GdIII doped with EuIII (1 at.% and 5 at.%) complexes with the ligand derived from 3,4,5-trihydroxybenzoic acid (H4Gal). Synthetic routes are proposed from acetate and chloride solutions of the trivalent lanthanides. We demonstrated the decomposition of the ligands 3,4,5-trihydroxybenzoate (H3Gal ≡ L–) and 3-hydroxo-4,5-dihydroxybenzoate (H2Gal2– ≡ L’2–) in an acetic solution medium. [LnLL’(H2O)2] complexes are obtained in a metal chloride solution medium. We studied the complexes in the solid state. We described the photophysical processes in the complexes, and they resulted in an energy diagram of the EuIII compounds in which the position of the states related to the LMCT transition are intermediate to the ligand's singlet (S1) and triplet (T1) states. We obtained the position of the triplet state (T1) from the luminescence of the GdIII complex. We performed the calculations of the EuIII complex's electronic structure using the Lumpac software to confirm the propositions obtained through experiments. The proposition is that the excitation in the LMCT state rapidly populates the T1 state, and the L–L’2–→EuIII back energy transfer may occur. One of the possible disadvantages of the complexes is the enormous non-radioactive deactivation due to the oscillators (OH) and (CH). The EuIII characteristic luminescence is of little intensity. We obtained GdIII compounds doped with EuIII at 1.0 and 5.0 at.% to optimize luminescent properties. We obtained the emission and excitation spectra of the complexes at 77 and 17 K, showing ligands' phosphorescence superimposed on the characteristic emissions 5D0 →7FJ (J = 0–4) of the EuIII ion.

Quantitative and Multiplexed Chopper-Based Time-Gated Imaging for Bioanalysis on a Smartphone.

Smartphones are emerging platforms for point-of-care diagnostics (POCDs), where the on-board camera is, for example, used to image fluorescence. Many laboratory instruments are capable of time-gated (TG) photoluminescence (PL) measurements─an analytical method leveraged by multiple commercial assay kits. When paired with long-lived PL emitters such as luminescent lanthanide complexes (LLCs), time-gating eliminates background from sample autofluorescence and many other sources. This capability is amenable to minimally processed samples and would thus be useful for POCDs on a smartphone-based platform. Here, we report a double-chopper design for TG PL imaging using a portable, 3D-printed, smartphone-based device. The rotation speed, dimensions, and overlap of the chopper blades and gaps set the timing parameters, with delay times on the order of hundreds of microseconds to milliseconds. The device was capable of quantitative TG imaging of PL from terbium(III) and europium(III) LLCs, including rejection of short-lived PL background from serum and tissue phantoms, spectral and temporal multiplexing, a model time-gated Förster resonance energy transfer (TG-FRET) assay, and imaging of cells. As the first smartphone-based demonstrations of these important analytical capabilities, this work is an important foundation for developing POCD methods based on TG PL imaging.

Mechanically induced structural transformations in luminescent gold complexes

Mechanically induced structural transformations in luminescent gold complexes

Population and decay of the HenICl(β1) clusters

The letter presents the results of studies of population and decay of the {2,0}He2ICl(β1,vβ = 0) and {1,1}He2ICl(β1,vβ = 0) clusters. Action, pump–probe and luminescence excitation spectra as well as luminescence spectra themselves have been measured. The T-shaped HeICl(E,vE = 0 andD′,vD′ = 0) complex luminescence has been observed when the {2,0}He2ICl(β1,vβ = 0) cluster is populated. It has been shown that a population of the {1,1}He2ICl(A,13,nA) cluster at the energy higher than its dissociation threshold is accompanied by the T-shaped HeICl(A,13,nA) formation.

Effects of water molecules on luminescence in europium and terbium coordination polymers with p-fluorobenzoic acid as ligand

Our previous experimental observations show that the crystal structure of lanthanide luminescent complexes synthesized in aqueous solution usually contains a large number of coordination water molecules or free water molecules. In order to probe the influence of water molecules on luminescent processes of lanthanide complexes, the photoluminescence properties of Ln-FBA (Ln = Eu and Tb, FBA = p-fluorobenzoic acid) coordination polymers at different ambient temperatures, in different solvents and aqueous DMSO solutions with different volume concentrations were systematically investigated. The experiment results show that the presence of water molecules can promote the energy transfer from FBA ligand to Ln3+, at the same time, can cause luminescent non-radiation quenching of lanthanide ions. In addition, the variation of emission intensity ratio of 615 nm/591 nm peaks of Eu3+ with increasing the volume concentration of H2O can be potentially used for the quantitatively detection of water traces in organic solvents. In order to suppress the non-radiation quenching caused by the water molecules, Ln-FBA (Ln = Eu and Tb) coordination polymers were embedded into the PVP matrix to prepare Ln-FBA@PVP hybrid materials. The photoluminescence investigation indicates that PVP can not only block the quenching effect of water molecules on luminescence, but also effectively sensitize Eu3+ and Tb3+ luminescence. These experimental conclusions are useful for probing the influence of water molecules on luminescent processes of lanthanide complexes, quantitatively detecting water traces in organic solvents and enhancing the photoluminescence intensity in lanthanide complexes.

Synthesis, structure of luminescence complexes and metalopolymers of Dy(III) and influence of the nature of substitutes on their emission

The new complexes of Dy (III) other β-diketones containing unsaturated, alkyl- and aryl- substituents were obtainted. Their heteroligand complexes with phenanthroline were synthesized. Quantum-chemical calculations of ligand molecules and metal complexes were performed. The main energy characteristics of ligand molecules were calculated: enthalpy of formation, total energy of the molecule and bond lengths, electronic population parameters of ligands. Metal polymers based on synthesized complexes were obtained by the method of radical polymerization. The composition and structure of synthesized complexes and metal polymers are established. It is shown that during polymerization the coordination environment of the central ion remains unchanged. The spectral-luminescent characteristics of the synthesized compounds were studied. The peculiarities of the influence of substituents in the diketonate fragment on the luminescent properties of metal complexes have been established. It is shown that the emission intensity of powdered samples depends on their morphology and dispersion.

Preparation and optical studies of octacoordinated luminescent complexes of Dy(III) derived from fluorinated β-diketone and heteroaromatic neutral ligands

A series of ternary complexes of dysprosium tris-β-diketonate was prepared by using phenanthroline and its substituted derivatives as neutral ligands. The complex formation or the coordination mode of organic moieties was analysed by elemental, infrared, proton NMR and UV–Visible analyses. The anhydrous nature of prepared complexes was illustrated by using thermogravimetric and infrared studies. The band gap was also measured which is present in the range of conducting zone. The luminescence characteristics were measured in solid and solution. The complex upon excitation under UV light generates emission in the yellow region which indicates proficient energy transference from coordinated moieties to the central Dy(III) ion. The correlated color temperature (CCT) of Dy(III) complexes has been calculated and found to be ∼ 5000 K which belongs to a cold light region. The contribution of 4F9/2 → 6H13/2 transition (75 %) is highest towards total radiative processes and it might be regarded as an acceptable transition for laser amplification. The prepared complexes of Dy(III) could be utilized in fabricating OLEDs and displays due to their band gap value, large thermal stability and high luminous characteristics.

Ion beam induced luminescence analysis of europium complexes in styrene-divinylbenzene copolymer-coated spherical silica by proton and argon ion beams irradiation

Ion beam induced luminescence (IBIL) analysis of adsorbents containing Eu complexes was carried out using a 3-MV single-ended accelerator and an azimuthally varying field cyclotron to evaluate structures of complexes in an extraction chromatography. Some adsorbents were prepared by impregnating a styrene-divinylbenzene copolymer-coated porous silica particle (SiO2-P) with extractants. The IBIL spectra of Eu complexes in the adsorbents produced some differences depending on the kinds of extractants. The experimental results imply that the difference in the IBIL spectra of Eu complexes in the adsorbents is caused by the difference in the structures. The only clear luminescence peak in the alkyl diamide amine (ADAAM) with n-octyl and 2-ethylhexyl alkyl chains (ADAAM(Oct, N(EH))) adsorbent was not observed by H+ ion beam irradiation. Meanwhile, the luminescence of Eu could be detected by irradiation of an Ar8+ ion beam. The luminescence of Eu complexes is presumed to be easily detected by high linear energy transfer (LET) beam irradiation. The symmetric properties of Eu complexes were evaluated with the luminescence due to the 5D0 → 7F2 transition, and it is implied that ADAAM with 2-ethylhexyl alkyl chains (ADAAM(EH, N(EH))) is a high asymmetry property. The luminescence intensity of Eu complexes in the adsorbent decreased with the ion beam irradiation because extractants were damaged by the ion beam. This phenomenon was clearly observed by irradiation of high LET ion beam, Ar8+.