4373-59-5Relevant articles and documents
A novel and robust heterogeneous Cu catalyst using modified lignosulfonate as support for the synthesis of nitrogen-containing heterocycles
Bai, Rongxian,Gu, Yanlong,Lai, Bingbing,Li, Minghao,Liu, Ping,Ye, Meng
supporting information, p. 2888 - 2902 (2020/12/22)
A waste biomass, sodium lignosulfonate, was treated with sodium 2-formylbenzenesulfonate, and the phenylaldehyde condensation product was then used as a robust supporting material to immobilize a copper species. The so-obtained catalyst was characterized by many physicochemical methods including FTIR, EA, FSEM, FTEM, XPS, and TG. This catalyst exhibited excellent catalytic activity in the synthesis of nitrogen-containing heterocycles such as tricyclic indoles bearing 3,4-fused seven-membered rings, 2-arylpyridines, aminonaphthalenes and 3-phenylisoquinolines. In addition, this catalyst showed to be recyclable and could be reused several times without significant loss in activity during the course of the reaction process.
Colour tuning by the ring roundabout: [Ir(C^N)2(N^N)]+ emitters with sulfonyl-substituted cyclometallating ligands
Ertl, Cathrin D.,Cerdá, Jesús,Junquera-Hernández, José M.,Pertegás, Antonio,Bolink, Henk J.,Constable, Edwin C.,Neuburger, Markus,Ortí, Enrique,Housecroft, Catherine E.
, p. 42815 - 42827 (2015/05/27)
A series of cationic bis-cyclometallated iridium(iii) complexes [Ir(C^N)2(N^N)]+ is reported. Cyclometallating C^N ligands are based on 2-phenylpyridine with electron-withdrawing sulfone substituents in the phenyl ring: 2-(4-methylsulfonylphenyl)pyridine (H1) and 2-(3-methylsulfonylphenyl)pyridine (H2). 2-(1H-Pyrazol-1-yl)pyridine (pzpy) and 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine (dmpzpy) are used as electron-rich ancillary N^N ligands. The complexes have been fully characterized and the single crystal structure of [Ir(2)2(dmpzpy)][PF6]·MeCN has been determined. Depending on the position of the methylsulfonyl group, the complexes are green or blue emitters with vibrationally structured emission maxima at 491, 523 nm for [Ir(1)2(N^N)][PF6] or 463, 493 nm for [Ir(2)2(N^N)][PF6] in MeCN solution. The marked vibrational structure and the absence of a rigidochromic shift, together with theoretical predictions based on density functional theory calculations, confirm the 3LC nature of the emitting triplet state. All four complexes have relatively high photoluminescence quantum yields in de-aerated solution (53 to 77%). On going from solution to powder samples, the emission is red-shifted and the quantum yields are considerably lower (≤11%). The complexes were tested in light-emitting electrochemical cells (LECs) achieving maximum luminances of 141 cd m-2 when operated at 100 A m-2 using pulsed current driving conditions.
Green-emitting iridium(iii) complexes containing sulfanyl- or sulfone-functionalized cyclometallating 2-phenylpyridine ligands
Constable, Edwin C.,Ertl, Cathrin D.,Housecroft, Catherine E.,Zampese, Jennifer A.
, p. 5343 - 5356 (2014/04/03)
A series of [Ir(C^N)2(bpy)][PF6] complexes in which the cyclometallating ligands contain fluoro, sulfane or sulfone groups is reported. The conjugate acids of the C^N ligands in the complexes are 2-(4-fluorophenyl)pyridine (H1), 2-(4-methylsulfonylphenyl)pyridine (H3), 2-(4-tbutylsulfanylphenyl)pyridine (H4), 2-(4- tbutylsulfonylphenyl)pyridine (H5), 2-(4- ndodecylsulfanylphenyl)pyridine (H6), 2-(4- ndodecylsulfonylphenyl)pyridine (H7). The single crystal structures of H3 and H5 are described. [Ir(C^N)2(bpy)][PF6] with C^N = 1, 3, 4, 5 and 7 were prepared from the appropriate [Ir2(C^N) 4Cl2] dimer and bpy; the structure of [Ir 2(3)4Cl2]·2CH2Cl2 was determined. [Ir(6)2(bpy)][PF6] was prepared by nucleophilic substitution starting from [Ir(1)2(bpy)][PF 6]. The [Ir(C^N)2(bpy)][PF6] complexes have been characterized by NMR, IR, absorption and emission spectroscopic and mass spectrometric methods. The single crystal structures of enantiomerically pure Δ-[Ir(1)2(bpy)][PF6] and of rac-4{[Ir(1) 2(bpy)][PF6]}·Et2O·2CH 2Cl2 are described, and the differences in inter-cation packing in the structures compared. [Ir(1)2(bpy)][PF6], [Ir(4)2(bpy)][PF6] and [Ir(6)2(bpy)][PF 6] (fluoro and sulfane substituents) are yellow emitters (λmaxem between 557 and 577 nm), and the room temperature solution emission spectra are broad. The sulfone derivatives [Ir(3)2(bpy)] [PF6], [Ir(5)2(bpy)][PF6] and [Ir(7) 2(bpy)][PF6] are green emitters and the emission spectra are structured (λmaxem = 493 and 523 to 525 nm). High photoluminescence quantum yields (PLQYs) of 64-74% are observed for the sulfone complexes in degassed solutions. The emission lifetimes for the three complexes containing sulfone substituents are an order of magnitude longer (2.33 to 3.36 μs) than the remaining complexes (0.224 to 0.528 μs). Emission spectra of powdered solid samples have also been recorded; the broad emission bands have values of λmaxem in the range 532 to 558 nm, and PLQYs for the powdered compounds are substantially lower (≤23%) than in solution. Trends in the redox potentials for the [Ir(C^N)2(bpy)][PF6] complexes are in accord with the observed emission behaviour. This journal is the Partner Organisations 2014.
