ORTEP Drawing Research Articles

An Aggregation-Induced Emission Optical Highlighter for the Studies of Endoplasmic Reticulum-Lipid Droplet Content Dynamics

An Aggregation-Induced Emission Optical Highlighter for the Studies of Endoplasmic Reticulum-Lipid Droplet Content Dynamics

Crystal Structure of 3-Bromo-7-(dimethylamino)-4-methylcoumarin

Coumarin derivatives are a useful component for developing new materials, such as fluorescence materials and laser dyes; non-linear optical materials and reagents; photorefractive materials; photoresistors; intermediates for drug synthesis; luminescence materials; analytical reagents, etc.1,2 Coumarin 311, 7-(dimethylamino)-4-methylcoumarin, is also used as laser dyes. It gives laser emission at around 453 nm in ethanol. The crystal structure of coumarin 311 has already been reported.3 However the fluorence property and crystal structure of 3-bromo-7-(dimethylamino)-4-methylcoumarin (1) has not yet been reported. We now report on the crystal structure of 1 with the aim of the contributing to a deeper understanding of the substituent effect at the 3-position of coumarin 311 on the structure and crystal packing. Compound (1), shown in Fig. 1, was synthesized by the reaction of 7-(dimethylamino)-4-methylcoumarin with bromine in glacial acetic acid, as reported in a previous paper.4 The spectral data of 1 are as follows: mp 168 – 169 C, 1H NMR (CDCl3) d 2.53 (3H, s), 3.06 (6H, s), 6.48 (1H, d, J = 2.6 Hz), 6.62 (1H, dd, J = 9.0 Hz, 2.6 Hz), and 7.43 (1H, d, J = 9.0 Hz). 13C NMR (CDCl3) d 19.15, 40.1(2C), 97.7, 106.2, 109.3, 109.4, 125.8, 151.5, 152.8, 154.1, and 158.0. Compound (1) gave a strong emission band at 442 nm in chloroform solution (1.0 ¥ 10–5 M) when excited at 380 nm. Single crystals of 1 were grown in chloroform at room temperature. Data collection and refinement parameters are listed in Table 1. The H atoms were positioned with the idealized geometry, and were refined to be isotropic (Uiso(H) = 1.2Ueq(C)) using a riding model with C–H = 0.95 A for aromatic H atoms and C–H = 0.98 A for methyl H atoms. The selected bond distances and angles are collected in Table 2. An ORTEP drawing of the molecule of 1 is shown in Fig. 2. The molecule is almost planar with a maximum deviation of –0.154(2)A for N1. The dihedral angle between the pyrone ring Crystal Structure of 3-Bromo-7-(dimethylamino)-4-methylcoumarin

Ab initio ORTEP drawings: a case study of N-based molecular crystals with different chemical nature

The thermal motion of atoms and functional groups is a key characteristic of any molecular crystal, and such motion derived from scattering experiments is conveniently visualised by means of thermal ellipsoids (the famous “ORTEP” drawings). Unfortunately, it is often impossible to obtain the underlying anisotropic displacement parameters (ADPs) for hydrogen atoms, due to their low X-ray scattering power, and sometimes no ADPs can be refined at all even for heavier atoms. In these cases, it would seem advantageous to estimate ADPs by first-principles techniques, and indeed such ab initio ORTEP plots have become available very recently. Here, we test this young method for a representative set of hydrogen-bonded molecular crystals: first, we study urea (CON2H4) as a well-known benchmark, then, its all-nitrogen analogue guanidine (CN3H5); finally, we move on to rubidium guanidinate (RbCN3H4) as a specimen with pronounced ionic interactions. For all three systems, ADPs have been obtained from density-functional theory (DFT) based phonon computations using the PHONOPY software. The results are compared with neutron-diffraction data as the experimental “benchmark” in this regard, and a critical discussion of experimental aspects is given. We observe excellent agreement between experiment and theory for the hydrogen-bonded systems urea and guanidine at low temperature, whereas high-temperature data for guanidine deviate visibly, and the more salt-like RbCN3H4 may suffer from a less-than-ideal description even at 12 K. Both are discussed in depth as there are possible solutions and directions for further research. Generally, the present results shine a favourable light on a future, more routine application of combined experimental/theoretical approaches in chemical crystallography.

Copper(II) and lead(II) complexes based on 2,3,5,6-tetrakis(2-pyridyl)pyrazine as a polydentate ligand

The Cu(II) complexes [Cu(Tppz)(Dipic)] · 8H2O (I) and [Pb2(Tppz)Cl4]n (II), where Tppz, H2Dipic are 2,3,5,6-tetrakis(2-pyridyl)pyrazine, dipicolinic acid, respectively, have been synthesized and characterized by elemental analyses, IR, cyclic voltammetry, and electronic spectral studies. Solid state structures of both complexes have been determined by single crystal X-ray crystallography. An ORTEP drawing of two complexes shows that the coordination geometry around the metal center is a distorted octahedron. There are extensive conventional intermolecular O-H…O, N-H…O, and weaker C-H…O and C-H…Cl non-classical hydrogen bonds, which cause the stability of the crystal structure. Crystal data for I: monoclinic, space group: C2/c, a = 35.421(3), b = 8.422(6), c = 22.824(8) A, β = 101.69(2)°, V = 6668(5) A3, Z = 8. Crystal data for II: triclinic, space group P\(\bar 1\), a = 7.9534(4), b = 8.8682(5), c = 9.4245(5) A, β = 95.086(2)°, V = 655.93(6) A3, Z = 2.

Synthesis, characterization, spectroscopic study, and catalytic behavior of ruthenium(II) o-phenanthroline complex with dipicolinate

A new dipicolinate complex of Ru(II), cis-[Ru(phen)2dipic] · 9.5H2O (1), where dipic is dipicolinate or pyridine-2,6-dicarboxylate and phen is 1,10-phenanthroline, has been synthesized and characterized by elemental analysis, spectroscopic (IR, UV-Vis), cyclic voltammetry, and single-crystal X-ray diffraction. ORTEP drawing of cis-[Ru(phen)2dipic] · 9.5H2O shows that the coordination geometry around Ru(II) is a distorted octahedron. It crystallizes in the triclinic system, with space group P 1, a = 10.4633(2) Å, b = 13.6332(4) Å, c = 13.6637(4) Å, α = 67.516(3)°, β = 69.757(2)°, γ = 77.201(2)°, V = 1680.74(8) Å3, Z = 2, and R int = 0.0311. In 1, two phen are bidentate N,N′ ligands. The Ru(II) in 1 is bonded to dipicolinate through pyridine nitrogen and one oxygen of carboxylate groups, thus pyridine-2,6-dicarboxylate is a bidentate N,O ligand. Efficient and selective oxidation of alcohols with NaIO4 as oxidant was conducted by this complex catalyst in CH3OH/H2O as solvents under air at room temperature.

Heterobimetallic Nitride Complexes from Terminal Chromium(V) Nitride Complexes: Hyperfine Coupling Increases with Distance

Terminal nitride complexes of rhenium, osmium and molybdenum can form complexes with either alkylating agents, Lewis acidic metal halides, or low-valent, coordinatively unsaturated metal complexes. The few reactions of this type with a first-row transition-metal complex are limited to vanadium. Recently, the nitride chemistry of the chromium(V) cation has been significantly expanded by introduction of a preparative route which is based on nitrogen transfer from [Mn(N)(salen)] (salen=N,N’-bis(salicylidene)ethylenediamine) to the chromium(V) cation. With a range of chromium nitride complexes at hand we have investigated their reactivity and found that nucleophilicity is a general property which can be observed during formation of imide complexes with, for example, the trityl cation, tris(pentafluorophenyl)boron, and methyl triflate. In addition we report that terminal chromium(V) nitride complexes coordinate through the nitride ligand to low-valent complexes of the platinum metals. These compounds are possible precursors to bimetallic nitride phases which are gaining in importance as heterogeneous catalysts in, for example, the Haber–Bosch process. Solutions of terminal chromium nitride complexes in noncoordinating solvents treated with electrophiles such as B(C6F5)3 or C(C6H5)3 + quickly yield intensely colored orangered or green solutions. The reactions proceed cleanly as shown by EPR spectra which display a signal from a single S= =2 spin species. Similar reactivity was observed in reactions with either [Rh(cod)Cl]2 or cis-[PtCl2(dmso)2] (cod= 1,5cyclooctadiene, dmso= dimethyl sulfoxide). Structures of some of these systems, characterized by single-crystal X-ray diffraction, are shown in Scheme 1. Experimental and crystallographic details such as ORTEP drawings andmetric parameters of complexes 1–5 (Scheme 1) are available in the Supporting Information (Tables S1 and S1a). Inspection of the structures reveals a number of general aspects: there is a strong propensity for the chromium center to increase its coordination number from five to six upon coordination of the nitride ligand. This propensity is expected and a consequence of the trans influence of either an imide or a bridging nitride ligand which is significantly lower than that of a terminal nitride ligand. Accompanying this, the displacement of Cr out of the plane spanned by the equatorial ligators is diminished from about 0.5 to about 0.2 . The Cr N bond length is elongated from 1.55 in the terminal nitride complexes to approximately 1.60–1.62 in the functionalized systems. Comparison of structure 1 with that of [Cr(N)(salen)] reveals that the metal–salen ligand bonds are significantly shorter when the nitride ligand is functionalized, as expected when two ligands compete for electron donation. However, for the systems derived from [Cr(N)(dbm)2] the situation is less clear (dbm= dibenzoylmethanolate). In complex 2 all the Cr–dbm bonds are longer than in the parent terminal nitride complex, while they are shorter or similar within the limits of uncertainty in complex 5. The B N and C N bonds in 1, 4, and 5 are unexceptional but the N Rh and N Pt bond lengths in 2 and 3 are at about 1.970 and 1.906 , respectively, and very short; the first value belongs to the top 5% of the shortest Rh N bonds and the second belongs to the top 1% of the shortest Pt N bonds. Table 1 compares the Pt N bond of 3 with Pt N bonds of other cis[PtCl2(dmso)L] structures. Scheme 1. Schematic representation of the chromium(V) imide and chromium(V) bridging-nitride complexes.

Mononuclear zinc(II) complex with 2,3,5,6-tetra(2-pyridyl)pyrazine

Complex [Zn(Tppz)Cl2] (I), where Tppz = 2,3,5,6-tetrakis(2-pyridyl)pyrazine, has been synthesized and characterized by elemental analyses, IR, 1H NMR, cyclic voltammetry, and electronic spectral studies. Solid state structures of the complex have been determined by single-crystal X-ray crystallography. The structural determination shows that the mononuclear complex I is a 1D coordination polymer. Also an ORTEP drawing of complex I shows that the coordination geometry around the Zn(II) center is slightly distorted from regular square-based pyramidal. Crystal data for I: triclinic, spase group P\( \bar 1 \), a = 10.171(2), b = 10.3550(13), c = 12.239 (2) A, α = 64.839(9)°, β = 85.736(8)°, γ = 77.842(10)°, V = 1140.3(4) A3, Z = 2.

Rhodium(III) and cadmium(II) complexes based on the polypyridyl ligand 2,3,5,6-tetrakis(2-pyridyl)pyrazine (tppz)

Tppz (2,3,5,6-tetrakis(2-pyridyl)pyrazine) complexes [Rh(tppz)(bpy)Cl][PF 6] 2.acetylacetone (bpy = 2,2′-bipyridine) and [{CdCl 2} 2(μ-tppz)].ethylene glycol have been synthesized and characterized by elemental analyses, IR, 1H NMR, cyclic voltammetry, photoluminescence and electronic spectral studies. Solid state structures of both complexes have been determined by single-crystal X-ray crystallography. The structural determination shows that the dinuclear Cd(II) complex, [{CdCl 2} 2(μ-tppz)], is a 1D coordination polymer. An ORTEP drawing of [Rh(tppz)(bpy)Cl][PF 6] 2.acetylacetone shows that the coordination geometry around the Rh(III) center is a distorted octahedron. [{CdCl 2} 2(μ-tppz)] displays intraligand 1(π–π ∗) fluorescence and can potentially serve as a photoactive material. For the mononuclear Rh(III) complex, only a two-electron reduction process occurs at the metal with the elimination of Cl − ligand. The emission of this complex is assigned as πd ∗ phosphorescence.

Total syntheses and structural revision of alpha- and beta-diversonolic esters and total syntheses of diversonol and blennolide C.

Total syntheses and structural revision of alpha- and beta-diversonolic esters and total syntheses of diversonol and blennolide C.

Transition metal-induced activation of alkynes leading to metal carbene species: synthetic application to new π-conjugated molecules

The in situ generation of furylcarbene complexes by means of transition metals was applied to catalytic carbene reactions, such as Wittig-type olefination and cycloisomerization reactions. In the presence of [Rh(OAc)2]2 as a catalyst and triphenylphosphine as a carbene accepter, carbonyl-ene-ynes 1a reacted with benzaldehyde to give a 2-styrylfuran derivative 3a. The reaction involving phosphine-ylide formation followed by Wittig-type olefination with aldehydes was applied to synthesis of furfurylidene-containing p-extended conjugated molecules. A Ruthenium catalyst underwent cycloisomerization of 1,2-bis(carbonylenyl)acetylene 10a,b to afford 2,2′-bifuran structures. The crystal structure of 5,5′-diphenyl-2,2′-bifuran 11b was determined by X-ray crystallography. The ORTEP drawings of 11b exhibited transoid and highly planar structure. The emission bands of the bisfuran 11b were observed at 414 and 440 nm, its quantum yield (84%) was higher than that of a similar 5,5′-diphenyl-2,2′-bithiophene.

Nitrogen–Carbon Bond Formation from N2 and CO2 Promoted by a Hafnocene Dinitrogen Complex Yields a Substituted Hydrazine

Nitrogen–Carbon Bond Formation from N₂ and CO₂ Promoted by a Hafnocene Dinitrogen Complex Yields a Substituted Hydrazine

Crystal structure, magnetic and electrochemical properties of five-coordinate copper (II) complexes with 1,10-phenanthroline-5,6-dione

Three new five-coordinate Cu II complexes, [Cu(tpy)(phen-dione)](PF 6) 2, [Cu(phen)(phen-dione)Cl]PF 6 and [Cu(bpy)(phen-dione)Cl]PF 6 (tpy = 2,2′;6′,2″-terpyridine, phen = 1,10-phenanthroline and phen-dione = 1,10-phenanthroline-5,6-dione) have been prepared and characterized by elemental analysis, IR and UV–Vis spectroscopies and cyclic voltammetry. The complex of [Cu(tpy)(phen-dione)](PF 6) 2 crystallized with one molecule of acetonitrile. The ortep drawing of [Cu(tpy)(phen-dione)](PF 6) 2 · CH 3CN shows that the coordination geometry around Cu II is a distorted trigonal- bipyramid. Due to the steric hindrance of PF 6 - in the unit cell, the tpy ligands in each complex cation cannot interact in a π–π fashion. The effective magnetic moment ( μ eff) of the complexes was measured by the Evans method. The cyclic voltammograms at Pt disk electrode for these complexes display only one reversible Cu(II)/Cu(I) redox couple.

Syntheses of Aromatic Substituted Hydrazino-thiazole Derivatives to Clarify Structural Characterization and Antioxidant Activity between 3-Arylsydnonyl and Aryl Substituted Hydrazino-thiazoles

This work clarifies the structural characterization and antioxidant activity between aromatic and 3-arylsydnonyl substituted hydrazino-thiazoles by further synthesizing a series of aromatic ring-substituted hydrazino-thiazole derivatives 8a-h and 9a-h. Hydrazino-thiazole derivatives 8a-h and 9a-h were obtained by reacting aromatic or heterocyclic aromatic aldehyde thiosemicarbazones 7a-h with cyclization reagents ethyl 2-chloroacetoacetate (2a) and 2-bromoacetophenone (2b), respectively. The ORTEP drawings of compounds 8g, 8h and 9f provide strong evidence of the structure of aromatic thiazole derivatives 8a-h and 9a-h. Undoubtedly, the structure of compounds 3e-h and 4e-h synthesized by the reaction of 3-aryl-4-formylsydnone thiosemicarbazones 1e-h with cyclization reagents 2a and 2b in the previous work should have the thiazole moiety, and not the thiazoline moiety. Both the new thiazole derivatives 8a-h and 9a-h and the 3-arylsydnonyl-substituted derivatives 3e-h and 4e-h were investigated to determine their antioxidant activity by two tests that have been highly documented-the direct scavenging effect on a stable free 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and the inhibition of the 2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical. Results of this study demonstrate that not only the thiazole ring and the aryl ring has the contribution to the antioxidant activities, the sydnone ring of 3-arylsydnonyl moiety also has its considerable contribution.

Synthesis and Characterization of Altaicadispirolactone.

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Synthesis, structure, spectroscopic, magnetic and electrochemical studies of Ni II phen-dione complex

The first crystal structure of Ni II phen-dione complex is reported. This compound is [Ni(bpy) 2(phen-dione)](PF 6) 2 (bpy = 2,2′-bipyridine and phen-dione = 1,10-phenanthroline-5,6-dione). The complex has been characterized by elemental analysis, IR and electronic absorption spectroscopy and cyclic voltammetry. The electrochemical behavior and electronic spectrum of [Ni(bpy) 2(phen-dione)](OAc) 2 has also been studied in buffered solutions at pH between 1 and 8. ORTEP drawing of [Ni(bpy) 2(phen-dione)](PF 6) 2 · 2CH 3CN shows that the coordination geometry around the Ni II is a distorted octahedron, with bite angles of 78.1–78.8° for all three bidentate ligands and the two pyridyl rings of the bpy ligands are nearly co-planar, as are the two pyridyl rings of phen-dione.

Synthesis and Characterization of High-Spin Cobalt(II)-Based “Inorgainc Tennis Ball”

The cavities in coordination boxes, cages, and capsules are attracting much attention because of their encapsulation, catalytic reaction, and stereoselective transformation properties. “Inorganic Tennis Ball” (“ITB”) was named to the supramolecule obtained from the self-assembly of Cu(BF4)2 and (dach)Pt(BETMP) (dach = trans-1,2-diaminocyclohexane and BETMP = bisethylthiomethylidenepropanedioate). The cavity and hydrophobic pocket in the ITB have shown recognition properties for anions and pyridine molecules. It is essential to modify the metal sites in order to induce novel magnetism, encapsulation or reaction properties from ITB. We have devoted efforts to find out other transition metals that can replace copper(II) in the ITB. We now report the synthesis and characterization of a new cobalt(II)-based ITB and its magnetic properties. BETMP is a multidentate ligand with two sulfur atoms and two carboxylate groups. A diamineplatinum(II) moiety, (dach)Pt(II), was reported to be coordinated to the ligand exclusively by two sulfur atoms while copper(II) ion, on the other hand, by carboxylate oxygens. To reveal the coordination property of cobalt(II) ion to the ligand, cobalt(II) sulfate and potassium sulfate was reacted with two equivalents of Ba[BETMP] in water. After stirring for 2 h, the precipitate (BaSO4) was removed by filtration, and recrystallization in methanol/ether of the crude product obtained by evaporation of the filtrate afforded the crystalline compound K2Co(BETMP)2(HOCH3)2 (1) (Figure 1). Two carboxylates and two methanols coordinate cobalt(II), where the distance from cobalt(II) to methanol oxygen is 2.165(4) A. Compound 1 was reacted with two equivalent (dach)Pt(NO3)2 in methanol. After removal of KNO3 by filtration, crystalline compound [[{(dach)Pt(BETMP)}2Co(OHCH3)]2(NO3)][NO3]3 (2·[NO3]3) was obtained by slow evaporation of the filtrate (Scheme 1). ESI-MS spectrum of the methanol solution of 2·[NO3]3 detected the ions of m/z = 784.7 and 1207.4 which corresponds to [2-(OHCH3)2] and [(2-(OHCH3)2)·NO3], respectively, unique ions proving the existence of the tennis ball structure in the solution. Figure 2 shows the crystal structure of of 2. Compound 2 is a dimer composed of two homo copies. Hydrogen bonding interactions between NH of one copy and carboxylate oxygens of the other (the distances of N...O range from 2.97 to 3.03 A) are important driving forces for the formation of the dimer. The close contacts between two sulfurs in different copies (these distances range from 3.62 to 3.75 A) seem to also contribute to the gathering of the two copies. A NO3− anion is centered at the cavity inside the dimer. The distance between Co(II) and methanol oxygen is 2.129(18) A. This distance, along with that of 1, is similar to those often observed in other cobalt complexes. Figure 3 shows the electron paramagnetic resonance (EPR) spectrum of the compound 2·[NO3]3 in frozen solution state. The broad EPR feature from 75 to 360 mT Figure 1. ORTEP drawing of the anionic part of 1. The molecule has inversion symmetry. Bond distances (A): Co(1)-O(1), 2.042(3); Co(1)-O(4), 2.076(3); Co(1)-O(5), 2.165(4).

Synthesis and Crystal Structure of (2-Hydroxy-5-methylphenyl)-(2-bromophenyl)methanone

The efficiency of benzophenone analogues as chemotherapeutic agents, especially as inhibitors of HIV-1 reverse transcriptase RT, cancer 1 and inflammatory, is well established and their chemistry has been extensively studied. Benzophenones are usually obtained from natural products 2 or by synthetic methods. 3 The importance of these substances is basically due to the diverse biological and chemical properties that they possess. Subsequently, benzophenones are frequently used in medicine and industry. In a typical procedure, 1 (10 g, 0.034 mol) was thoroughly mixed with montmorillonite K 10 clay (1:3 w/w) in the solid state using a vortex mixer and subjected to microwave irradiation at 40% power for 5 min. The completion of the reaction was monitored on TLC and the product was extracted into ether. Finally, it was isolated and recrystallized and the yield of 2 was 89%. A schematic diagram of the molecule is shown in Fig. 1. A single crystal of the title compound with dimensions of 0.3 × 0.3 × 0.3 mm was chosen for X-ray diffraction studies. The crystal and experimental details are given in Table 1. The data were collected on the DIPLabo Image Plate system with graphite-monochromated Mo Kα radiation. Thirty six frames of data were collected in oscillation mode with an oscillation range of 5˚ and processed using Denzo. 4 The reflections were merged with Scalepack. All of the frames could be indexed using primitive monoclinic lattice. The structure was solved by direct methods using SHELXS-97.5 The structure was refined by full-matrix least squares method with anisotropic temperature factors for non-hydrogen atoms using SHELXL-97.5 The hydrogen atoms were fixed at chemically acceptable positions, and were refined with isotropic temperature factors. An ORTEP drawing of the molecule with thermal ellipsoids at 40% probability is shown in Fig. 2. The substitution at the 2-position can promote a steric hindrance that results in the large asymmetry of the molecule (viewed along the C=O bond). The title molecule is indeed asymmetric. The bond length C8‐C10 is 1.454(6)A and C5‐C8 x43

Synthesis and Characterization of Altaicadispirolactone

Altaicadispirolactone was synthesized via a simple route. In this route, levulinic acid was used as a starting material, and bromination followed by hydrolysis and BF3 · OEt2‐catalyzed cyclization were carried out. A single‐crystal ORTEP drawing has been created and more detailed crystallographic data of the compound has been obtained from X‐ray analysis.

Synthesis, structure and spectroscopic study of Rh III polypyridine complexes with phenylcyanamide derivative ligands

Several new Rh III complexes, [Rh(tpy)(bpy)L](PF 6) 2 (tpy=2,2′:6′,2″-terpyridine, bpy=2,2′-bipyridine, and L=monoanions of phenylcyanamide(pcyd)), 4-methylphenylcyanamide (4-MePcyd), 2,4-dimethylphenylcyanamide (2,4-Me 2pcyd), 4-methoxyphenylcyanamide (4-MeOPcyd), 2-chlorophenylcyanamide (2-Clpcyd) and 2,5-dichlorophenylcyanamide (2,5-Cl 2pcyd) have been synthesized and characterized by elemental analysis, IR, 1H NMR and electronic absorption spectroscopies. ORTEP drawing of [Rh(tpy)(bpy)(2,5-Cl 2pcyd)](PF 6) 2·1/2CH 3CN shows three pyridyl rings of the tpy ligand that are nearly coplanar, as are the two rings of bpy. The anionic cyanamide group is coordinated end-on by the nitrile nitrogen to the Rh III. The Rh III–NCN bond is bent, having an angle of 125.4°. This bent bond is largely determined by the σ-bonding interaction of a cyanamide non-bonding electron pair in a sp 2 hybrid orbital.

Doubly ortho-linked quinoxaline/triarylamine hybrid as a bifunctional, dipolar electroluminescent template for optoelectronic applications

The titled hybrid (Q-H) works as a clippable optoelectronic unit. Q-spacer-Q systems function as efficient orange emitters reaching EL intensities (L) of up to 6840 cd m-2 with etaext of 0.77% and operation efficiencies of 1.60 cd A-1 and 0.8 lm W-1. Notably, Q-An acts as a (bluish) green emitter, reaching L of 12347 cd m-2 with similar operational efficiency.