Mono- and Dinuclear Cationic Iridium(III) Complexes Bearing a 2,5-Dipyridylpyrazine (2,5-dpp) Ligand

Donato, Loïc; McCusker, Catherine E.; Castellano, Felix N.; Zysman‐Colman, Eli

doi:10.1021/ic400478d

Cited by 71 publications

(68 citation statements)

References 114 publications

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“…5 Å. 23,26,27,32,34,40,47 (It is noteworthy that with [Ir(ppy) 2 µ-Cl] 2 -type complexes where the Ir-Ir distances are <4 Å only the less sterically congested rac ΔΔ/ɅɅ diastereomers have been reported to date [15][16][17][18]39,[48][49][50][51][52][53][54][55] ). For 13-16 the diastereomers were separated by fractional crystallization, silica column chromatography, or a combination of the two techniques.…”

Section: Synthesismentioning

confidence: 99%

“…1, 2 and 3 ( Figure 1). [18][19][20][21][22][23][24][25][26][27][28][29] Consequently, for luminescence applications research has primarily concentrated on monoiridium complexes. 30,31 Nevertheless, the study of phosphorescent diiridium complexes is a rapidly expanding topic and a range of complexes with various conjugated bridging ligands have been reported to possess efficient photo-(PL) and electroluminescence (EL).…”

Section: Introductionmentioning

confidence: 99%

“…[44][45][46] In diiridium complexes, which incorporate conjugated bridging ligands, theoretical calculations often predict that a degree of frontier orbital character is localized on the bridging unit. 23,26,29,32,35,[37][38][39][40]42 In these cases a highly flexible bridge is expected to promote nonradiative processes and weaken emission. Consequently, the majority of the reported diiridium complexes that possess high solution state PLQYs incorporate rigid bridging units (such as compounds 4 and 6).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Diastereomer Separation, and Optoelectronic and Structural Properties of Dinuclear Cyclometalated Iridium(III) Complexes with Bridging Diarylhydrazide Ligands

et al. 2017

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(2017) 'Synthesis, diastereomer separation, and optoelectronic and structural properties of dinuclear cyclometalated iridium(III) complexes with bridging diarylhydrazide ligands. ', Organometallics., 36 (5). pp. 981-993.Further information on publisher's website:https://doi.org/10.1021/acs.organomet.6b00887Publisher's copyright statement:This document is the Accepted Manuscript version of a Published Work that appeared in nal form in Organometallics, copyright c 2017 American Chemical Society after peer review and technical editing by the publisher. To access the nal edited and published work see https://doi.org/10.1021/acs.organomet.6b00887. Additional information:Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. ABSTRACT: A series of diiridium complexes 13-16 bridged by diarylhydrazine ligands and cyclometalated by phenylpyridine or phenylpyrazole ligands was synthesized. In all cases the ɅΔ meso and ɅɅ/ΔΔ rac diastereomers were separated and characterized by single-crystal X-ray diffraction, revealing intramolecular - stacking between arenes of the bridging and cyclometalating ligands. Density functional theory (DFT) calculations show that in general the HOMOs are mainly localized on the iridium centers, the cyclometalating phenyl moieties and the central hydrazide components of the bridging ligands, while the LUMOs are primarily localized on the N-heterocycles (pyridine or pyrazole) of the cyclometalating ligands. This series of complexes, especially with the separated diastereomers, provides an ideal opportunity to study the effects of subtle structural changes on the optoelectronic properties of diiridium systems: significant differences are observed between the rac and meso isomers in some cases. A cyclic voltammetric study of the electrochemical properties of the eight complexes reveals strong intramolecular interactions between the iridium centers. The photophysical properties are reported in solution, and in rigid poly(methyl methacrylate) (PMMA) or 2-methyltetrahydrofuran (2-MeTHF) (at 77 K) matrices where some of the complexes are strongly emissive in the turquoise and green regions (Φ PL 42-68 ±10%) due to matrix-induced restricted intramolecular motion (RIM).

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Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Diastereomer Separation, and Optoelectronic and Structural Properties of Dinuclear Cyclometalated Iridium(III) Complexes with Bridging Diarylhydrazide Ligands

et al. 2017

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“…[30] They are synthetically versatile,a llowing facile tuningo ft he emission color via modification of the cyclometalating (C^N) and/or ancillary ligand structure. [30][31][32] Severale xamples of polynuclear cyclometalated iridiumc omplexes have been reported recently, [33][34][35][36][37][38][39] as well as some supramolecular structures where cyclometalated iridium is combinedw ith another photoactive metal complex. [15,[40][41][42][43][44][45][46] Relevant to the presentm anuscript,t here are af ew multimetallicc ompounds [15][16][17] involving cyclometalated iridiump artnered with Pt II bis-acetylide complexes,t he latter being anotherw ell-knownc lass of phosphorescent organometallic complexes.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Luminescent Ir–Pt–Ir Trimetallic Complexes

Song

Teets

2019

Chemistry A European J

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A new class of luminescent, heterotrimetallic supramolecular constructs partnering two bis‐cyclometalated iridium centers with a diimine platinum acetylide center is introduced. Whereas most supramolecular constructs featuring cyclometalated iridium involve elaborate bridging ligands and are prepared under forcing conditions with low to moderate yields, the three Ir–Pt–Ir complexes described here are prepared at room temperature from simple precursors and isolated in near‐quantitative yields. ESI‐MS, NMR spectroscopy, and diffusion ordered spectroscopy confirm the identity and homogeneity of the trimetallic products. In comparison with monometallic model complexes, analysis of UV/Vis absorption, steady‐state photoluminescence and time‐resolved emission reveals the impacts of supramolecular assembly on the photophysical properties. UV/Vis absorption and cyclic voltammetry suggest perturbation of some frontier orbital energies as a result of assembly, and the emission spectra and lifetimes reveal efficient excited‐state energy transfer via a Dexter mechanism, and show that the site of luminescence (platinum or iridium) depends on the identity of the cyclometalating ligand bound to iridium.

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“…[35][36][37][38] Herein, we designed and synthesized a series of 20 new dinuclear iridium(III) complexes (Ir1-Ir7, Scheme 1) as mitochondrial probes. Confocal fluorescence microscope and inductively coupled plasma mass spectrometry (ICP-MS) analyses demonstrated that complexes Ir2-Ir7 entered live cells through an endocytosis pathway and lighted up mitochondria 25 specifically.…”

Section: Introductionmentioning

confidence: 99%

Dinuclear iridium(iii) complexes as phosphorescent trackers to monitor mitochondrial dynamics

Chen

Zuo

et al. 2015

J. Mater. Chem. B

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5Mitochondria dynamic processes are essential for mammalian development and engaged in several diseases. However, commercial mitochondrial probes are currently too limited to satisfactorily track these dynamics. In this present work, seven dinuclear iridium(III) complexes [(ppy) 2 Ir(L 1-7 )Ir(ppy) 2 ] 2+ (Ir1-Ir7, ppy = 2-phenylpyridine, L = 1,3-bis(1-substituted-1H-imidazo[4,5-f][1,10]phenanthroline-2-yl)benzene) were synthesized. Possessing high specificity to mitochondria, low cytotoxicity and high resistance to the 10 loss of mitochondrial membrane potential, Ir2-Ir7 can serve as mitochondrial imaging dyes. Ir3 and Ir6 are further developed to track the mitochondrial morphological changes during the early stages of apoptosis. In addition, the relationship of the electron drawing/withdrawing groups in these systems with the photophysical properties and photostability is also discussed. 65 to red. 18 Recently, Grazulevicius and co-workers reported the development of the "warm-white" OLEDs that based on the application of bifunctional molecules via attachment of carbazole-based fragments to the phosphorescent iridium(III) complexes core. The triplet excited state of these bimolecular 70 complex were confirmed by the DFT and (TD) DFT methods. [19][20] In addition to OLED, iridium(III) complexes have also been applied as sensors, 21-22 in vivo tumour imaging, 23-24 , live cell compartmentalization staining and so on. Huang, Li and Schubert have reviewed these fields. [25][26][27] It is interesting that various 75 iridium(III) complexes have been developed as cytoplasm, nucleus, nucleolus, Golgi apparatus, lysosomes and vacuoles imaging dyes, 28-31 reports on iridium(III) complexes as mitochondrial dyes are quite less, although cationic species are Graphical AbstractDinuclear iridium(III) complexes [(ppy) 2 Ir(L 1-7 )Ir(ppy) 2 ] 2+ (Ir1-Ir7) serve as mitochondrial imaging dyes, Ir3 and Ir6 are further developed to track the mitochondrial morphological changes during the early stages of apoptosis.

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Mono- and Dinuclear Cationic Iridium(III) Complexes Bearing a 2,5-Dipyridylpyrazine (2,5-dpp) Ligand

Cited by 71 publications

References 114 publications

Synthesis, Diastereomer Separation, and Optoelectronic and Structural Properties of Dinuclear Cyclometalated Iridium(III) Complexes with Bridging Diarylhydrazide Ligands

Synthesis, Diastereomer Separation, and Optoelectronic and Structural Properties of Dinuclear Cyclometalated Iridium(III) Complexes with Bridging Diarylhydrazide Ligands

Facile Synthesis of Luminescent Ir–Pt–Ir Trimetallic Complexes

Dinuclear iridium(iii) complexes as phosphorescent trackers to monitor mitochondrial dynamics

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