676525-77-2

Usage

Uses

Used in Chemical Synthesis Industry:
[Ir(dtbbpy)(ppy)2][PF6] is used as a photocatalyst for driving photochemical reactions, such as the coupling of N-arylamines and nitroalkanes via an oxidative aza-Henry reaction. This reaction is essential for the synthesis of various organic compounds and pharmaceuticals.
Used in Polymer and Material Science:
[Ir(dtbbpy)(ppy)2][PF6] is used as a photocatalyst for the atom transfer radical addition (ATRA) of haloalkanes to alkenes and alkynes. This process is vital for the synthesis of new polymers and materials with unique properties and potential applications in various industries.
Used in Pharmaceutical Industry:
[Ir(dtbbpy)(ppy)2][PF6] is used as a photocatalyst for the conversion of 2-bromoanilides to the corresponding 3,3-disubstituted oxindoles. This transformation is crucial for the synthesis of bioactive compounds and drug candidates with potential therapeutic applications.
Used in Organic Chemistry Research:
[Ir(dtbbpy)(ppy)2][PF6] is used as a photocatalyst for aryl-alkyl C-C reductive cross-coupling reactions. This reaction is essential for the synthesis of complex organic molecules and the development of new synthetic methods in organic chemistry.

Reaction

This Iridium catalyst is used in the synthesis of β-amidovinyl sulfones via visible-light photoredox catalysis. Numerous uses of this photoredox catalyst are reported

Upstream product

• 72914-19-3 4,4'-di-tert-butyl-2,2'-bipyridine 
• 26042-63-7 silver(I) hexafluorophosphate 
• 17084-13-8 potassium hexafluorophosphate 
• 870987-64-7 bis-(μ)-chlorotetrakis[2-(2’,4’-difluorophenyl)-5-trifluoromethylpyridinato]-(C2,N)diiridium(III) 

Relevant academic research and scientific papers

Potential-Resolved Multicolor Electrochemiluminescence for Multiplex Immunoassay in a Single Sample

Electrochemiluminescence (ECL) is a highly successful technique used in commercial immunoassays for clinical diagnosis. Developing an ECL-based multiplex immunoassay, with the potential to enable high-throughput detection of multiple biomarkers simultaneously, remains a current research interest yet is limited by a narrow choice of ECL luminophores. Herein we report the synthesis, photophysics, electrochemistry, and ECL of several new ruthenium(II) and iridium(III) complexes, three of which are eventually used as signal reporters for multiplex immunoassay. The ECL behaviors of individual luminophores and their mixtures were investigated in multiple modes, including light intensity, spectrum, and image measurements. The spectral peak separation between Ru(bpy)2(dvbpy)2+ (bpy = 2,2′-bipyridine, dvbpy = 4,4′-bis(4-vinylphenyl)-2,2′-bipyridine), and Ir(dFCF3ppy)2(dtbbpy)+ (dFCF3ppy = 3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl]phenyl, dtbbpy = 4,4′-bis(tert-butyl)-2,2′-bipyridine) was up to 145 nm, thus providing the spectrum-resolved possibility of identifying light signals. The potential-resolved ECL signals were achieved for the mixtures of Ir(ppy)3 (ppy = 2-phenylpyridine) with either Ru(bpy)2(dvbpy)2+ or Ir(dFCF3ppy)2(dtbbpy)+, due to the self-annihilation ECL of Ir(ppy)3 at higher potentials, as confirmed by electrochemistry-coupled mass spectrometry. A multiplex immunoassay free of spatial spotting antibodies on plates or substrates was ultimately devised by combining luminophore-loaded polymer beads with the homogeneous sandwich immunoreaction. Using potential and spectrum dual-resolved ECL as the readout signal, simultaneous recognition of three antigens, namely, carcinoembryonic antigen (CEA), alpha-fetoprotein (AFP), and beta-human chorionic gonadotropin (β-HCG), was demonstrated in a single run for a sample volume of 300 μL. These results contribute to the understanding of ECL generation by multiple luminophores and devising spot-free multiplex immunoassays with less sample consumption.

Luminescence switch-on assay of interferon-gamma using a G-quadruplex-selective iridium(III) complex

In this study, we synthesized a series of 9 luminescent iridium(iii) complexes and studied their ability to function as luminescent probes for G-quadruplex DNA. The iridium(iii) complex 8 [Ir(pbtz)2(dtbpy)]PF6 (where pbtz = 2-phenylbenzo[d]thiazole; dtbpy = 4,4′-di-tert-butyl-2,2′-bipyridine) showed high selectivity for G-quadruplex DNA over single-stranded and double-stranded DNA, and was subsequently utilized for the development of a label-free oligonucleotide-based assay for interferon-gamma (IFN-γ), an important biomarker for a range of immune and infectious diseases, in aqueous solution. We further demonstrated that this assay could monitor IFN-γ levels even in the presence of cellular debris. This assay represents the first G-quadruplex-based assay for IFN-γ detection described in the literature.

Impact of the use of sterically congested Ir(iii) complexes on the performance of light-emitting electrochemical cells

The synthesis, structural and optoelectronic characterization of a family of sterically congested cyclometalated cationic Ir(iii) complexes of the form [Ir(C^N)2(dtBubpy)]PF6 (with dtBubpy = 4,4′-di-tert-butyl-2,2′-bipyridine and C^N = a cyclometalating ligand decorated at the 4-position of the pyridine ring and/or the 3-position of the phenyl ring with a range of sterically bulky substituents) are reported. This family of complexes is compared to the unsubstituted analogue complex R1 bearing 2-phenylpyridinato as cyclometalating ligand. The impact of sterically bulky substituents on the C^N ligands on both the solid state photophysics and light-emitting electrochemical cell (LEEC) device performance is investigated. X-ray diffraction analysis of complexes 1a, R2, 2a, and 1b show an increasing internuclear distance in the solid state, within these four complexes. Emission studies in solution and neat film show that the chosen substituents essentially do not impact the emission energy. The photoluminescence quantum yields (ΦPL) are in the same range (ΦPL ～ 25-31%), except for 1b, which shows a lower ΦPL of 12%. All complexes exhibit similar monoexponential emission lifetimes in the submicrosecond regime. LEECs based on R1, 1a, 1b and R2 were fabricated, showing yellow luminescence and moderate efficiencies and lifetimes. The arguably best performing LEEC device, showing the highest luminance (737 cd m-2), current efficiency (7.4 cd A-1) and EQE (2.6%), employed emitter 1a.

Chemical modification of dehydrated amino acids in natural antimicrobial peptides by photoredox catalysis

Dehydroalanine (Dha) and dehydrobutyrine (Dhb) are remarkably versatile non-canonical amino acids often found in antimicrobial peptides. This work presents the selective modification of Dha and Dhb in antimicrobial peptides through photocatalytic activation of organoborates under the influence of visible light. Ir(dF(CF3)ppy)2(dtbbpy)PF6 was used as a photoredox catalyst in aqueous solutions for the modification of thiostrepton and nisin. The mild conditions and high selectivity for the dehydrated residues show that photoredox catalysis is a promising tool for the modification of peptide-derived natural products.

The coupling of potassium organotrifluoroborates with Baylis–Hillman derivatives via visible-light photoredox catalysis

Catalyzed by Ir[dF(CF3)ppy]2(dtbbpy)PF6, the coupling of potassium organotrifluoroborates with Baylis–Hillman derivatives under visible light irradiation has been developed. Based on the mechanism of reductive quenching cycle, it provides an easy, mild, efficient method for the synthesis of a variety of α,β-unsaturated carboxylic esters derivatives in a broad scope of the substrates.

Microwave-Assisted Synthesis of Heteroleptic Ir(III)+ Polypyridyl Complexes

We report a rapid, one-pot, operationally simple, and scalable preparation of valuable cationic heteroleptic iridium(III) polypyridyl photosensitizers. This method takes advantage of two consecutive microwave irradiation steps in the same reactor vial, avoiding the need for additional reaction purifications. A number of known heteroleptic iridium(III) complexes are prepared in up to 96% yield. Notably, this method is demonstrated to provide the synthetically versatile photosensitizer [Ir(ppy)2(dtbbpy)]PF6 in >1 g quantities in less than 5 h of bench time. We envision this method will help accelerate future developments in visible-light-dependent chemistry.

The effect of photocatalyst excited state lifetime on the rate of photoredox catalysis

Four different iridium(iii) polypyridyl complexes with varying excited state lifetimes are used as photocatalysts to study the effect of excited state lifetime on the rate of a prototypical photoredox-catalyzed reaction, the trifluoromethylation of quinoline. An improved mechanistic understanding of the photocatalysis is achieved, enabling guided optimization of reaction conditions and elucidating the role of the photocatalyst excited state lifetime on the rate of photocatalysis.

Generation of Alkoxyl Radicals by Photoredox Catalysis Enables Selective C(sp3)-H Functionalization under Mild Reaction Conditions

Reported herein is the first visible-light-induced formation of alkoxyl radicals from N-alkoxyphthalimides, and the Hantzsch ester as the reductant is crucial for the reaction. The selective hydrogen atom abstraction by the alkoxyl radical enables C(sp3)-H allylation and alkenylation reactions under mild reaction conditions at room temperature. Broad substrate variations, including a structurally complexed steroid, undergo the C(sp3)-H functionalization reaction effectively with high regio- and chemoselectivity.

Copper-catalyzed asymmetric sp3 C-H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

This report describes a highly enantioselective oxidative sp3 C-H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)2(dtbbpy)]PF6, and chiral copper catalysts provide a mild and highly effective sp3 C-H asymmetric arylation of THIQs.

Efficient merging of copper and photoredox catalysis for the asymmetric cross-dehydrogenative-coupling of alkynes and tetrahydroisoquinolines

A highly efficient catalytic asymmetric alkynylation of prochiral CH2 groups in tetrahydroisoquinoline was developed using copper catalyzed cross-dehydrogenative-coupling of sp3 and sp C-H bonds with the assistance of a photocatalyst and visible light.