Facilitating triplet energy-transfer in polymetallayne-based phosphorescent polymers with iridium(III) units and the great potential in achieving high electroluminescent performances

Huang, Zuan; Liu, Boao; He, Yue; Yan, Xiaogang; Yang, Xiaolong; Xu, Xianbin; Zhou, Guijiang; Ren, Yanwei; Wu, Zhaoxin

doi:10.1016/j.jorganchem.2015.06.030

Cited by 11 publications

(4 citation statements)

References 56 publications

(23 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The greater stability, with regard to oxidation, of D2 indicates that for D1 the quinoidal character of the p-bis-amino motif is important and reaction of this moiety after oxidation may compete effectively with carbazole dimerization. Compound I1, prepared from APC (aminophenyl carbazole) by reaction with cyclohexyl-1,2-dicarboxy anhydride was dimerized by chemical oxidation 64,65 to yield model compound I2. Dimerization of I1 to form I2 results in broadening of the UV absorption bands and a redshift in the emission (Figure 5), as observed for D1/D2.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Reversible Charge Trapping in Bis-Carbazole-Diimide Redox Polymers with Complete Luminescence Quenching Enabling Nondestructive Read-Out by Resonance Raman Spectroscopy

et al. 2017

View full text Add to dashboard Cite

The coupling of substituted carbazole compounds through carbon–carbon bond formation upon one-electron oxidation is shown to be a highly versatile approach to the formation of redox polymer films. Although the polymerization of single carbazole units has been proposed earlier, we show that by tethering pairs of carbazoles double sequential dimerization allows for facile formation of redox polymer films with fine control over film thickness. We show that the design of the monomers and in particular the bridging units is key to polymer formation, with the diaminobenzene motif proving advantageous, in terms of the matching to the redox potentials of the monomer and polymer film and thereby avoiding limitations in film thickness (autoinsulation), but introduces unacceptable instability due to the intrinsic redox activity of this moiety. The use of a diimide protecting group both avoids complications due to p-diamino-benzene redox chemistry and provides for a redox polymer in which the photoluminescence of the bis-carbazole moiety can be switched reversibly (on/off) with redox control. The monomer design approach is versatile enabling facile incorporation of additional functional units, such as naphthalene. Here we show that a multicomponent carbazole/naphthalene containing monomer (APCNDI) can form redox polymer films showing both p- and n- conductivity under ambient conditions and allows access to five distinct redox states, and a complex electrochromic response covering the whole of the UV/vis–NIR spectral region. The highly effective quenching of the photoluminescence of both components in poly-APCNDI enables detailed characterization of the redox polymer films. The poly-APCNDI films show extensive charge trapping, which can be read out spectroscopically in the case of films and is characterized as kinetic rather than chemical in origin on the basis of UV/vis–NIR absorption and resonance Raman spectroscopic analyses. The strong resonantly enhanced Raman scattering for the various oxidized and reduced states of APCNDI enables nondestructive “read-out” of the state of the polymer, including that in which charges are trapped kinetically at the surface, making poly-APCNDI highly suitable for application as a component in organic nonvolatile memory devices.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Compound I1 , prepared from APC (aminophenyl carbazole) by reaction with cyclohexyl-1,2-dicarboxy anhydride was dimerized by chemical oxidation , to yield model compound I2 . Dimerization of I1 to form I2 results in broadening of the UV absorption bands and a redshift in the emission (Figure ), as observed for D1/D2 .…”

Section: Resultsmentioning

confidence: 99%

Reversible Charge Trapping in Bis-Carbazole-Diimide Redox Polymers with Complete Luminescence Quenching Enabling Nondestructive Read-Out by Resonance Raman Spectroscopy

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Suzuki–Miyaura cross-coupling reactions are powerful tools for forming carbon–carbon bonds (eq ) with broad applications in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals, as well as in the total synthesis of natural products . The search for new materials is also not alien to their value . Starting from iridium(III) complexes containing cyclometalated 2-phenylpyridine or related ligands, these reactions have been successfully employed in the preparation of emissive polymers and dendrimers .…”

mentioning

confidence: 99%

Suzuki–Miyaura Cross-Coupling Reactions for Increasing the Efficiency of Tris-Heteroleptic Iridium(III) Emitters

et al. 2019

View full text Add to dashboard Cite

The complex Ir(acac){κ2-C,N-[C6BrH3-py]}{κ2-C,N-[C6H4-py]} (2) is a green emitter, which displays short lifetimes (0.9–4.9 μs) and quantum yields of 0.32 in poly(methyl methacrylate) films at 5 wt % and 0.41 in 2-methyltetrahydrofuran at room temperature. Its Pd(OAc)2/4 PPh3-catalyzed cross-coupling reactions with RB(OH)2 afford Ir(acac){κ2-C,N-[C6RH3-py]}{κ2-C,N-[C6H4-py]} (R = Me (3), Ph (4)), which show almost identical emissions with quantum yields in the range 0.98–0.82.

show abstract

“…The absolute metal-centered configuration was assigned by CD spectroscopy through comparison with published nonbrominated analogues . In the subsequent key step, the individual brominated diastereomers were cross-coupled with suitable boronic esters in order to introduce the linker unit. , For example, Λ-( S )- Ir1 was reacted with the boronic ester 3a or 3b in the presence of Pd(OAc) 2 , the ligand SPhos (20 mol %), and K 3 PO 4 at 80 °C to afford the complex Λ-( S )- Ir2a (76%) or Λ-( S )- Ir2b (77%), respectively. Next, protecting groups were removed to provide Λ-( S )- Ir3a (TBS removal with TBAF, 90%) containing a primary alcohol and Λ-( S )- Ir3b (Cbz removal with H 2 and Pd/C, 93%) containing a primary amine.…”

mentioning

confidence: 99%

Polymer-Supported Chiral-at-Metal Lewis Acid Catalysts

et al. 2017

View full text Add to dashboard Cite

The covalent immobilization of a chiral-at-metal biscyclometalated iridium(III) catalyst on a solid support is reported, and its catalytic activity has been investigated. As a catalyst immobilization strategy, a catalyst precursor was tethered to polystyrene macrobeads through an ester or amide linkage and subsequently converted to the immobilized active chiral Lewis acid by treatment with a Brønsted acid. The amide-linked catalyst displays high robustness and can be recycled multiple times without deterioration of enantioselectivity and only a gradual loss of catalytic activity. Chiral Lewis acid activity was demonstrated as an example for the enantioselective Friedel−Crafts alkylation of indole with an α,β-unsaturated 2-acyl imidazole and for the enantioselective Diels−Alder reactions of an α,β-unsaturated 2-acyl imidazole with 2,3-dihydrofuran or isoprene.

show abstract

Facilitating triplet energy-transfer in polymetallayne-based phosphorescent polymers with iridium(III) units and the great potential in achieving high electroluminescent performances

Cited by 11 publications

References 56 publications

Reversible Charge Trapping in Bis-Carbazole-Diimide Redox Polymers with Complete Luminescence Quenching Enabling Nondestructive Read-Out by Resonance Raman Spectroscopy

Reversible Charge Trapping in Bis-Carbazole-Diimide Redox Polymers with Complete Luminescence Quenching Enabling Nondestructive Read-Out by Resonance Raman Spectroscopy

Suzuki–Miyaura Cross-Coupling Reactions for Increasing the Efficiency of Tris-Heteroleptic Iridium(III) Emitters

Polymer-Supported Chiral-at-Metal Lewis Acid Catalysts

Contact Info

Product

Resources

About