Synthesis, UV–Vis and CV properties of a structurally related series of bis(Arylimino)acenaphthenes (Ar‐BIANs)

Hasan, Kamrul; Zysman‐Colman, Eli

doi:10.1002/poc.3081

Cited by 43 publications

(58 citation statements)

References 49 publications

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“…Cyclic voltammetry : To quantify the different redox properties of the R DAB R′ ligands, cyclic voltammetry (CV) was employed. Analogous CV investigations on a series of R BIAN ligands have been reported recently and confirm that such ligands are always much easier to reduce than the corresponding DAB ligands: for example, the first reduction wave for Mes BIAN is found at approximately −0.97 V versus a standard hydrogen electrode (SHE) 46–48…”

Section: Resultssupporting

confidence: 74%

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Non‐Innocent Ligand Effects on Low‐Oxidation‐State Indium Complexes

Allan

Cooper

Cowley

et al. 2013

Chemistry A European J

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Attempts to coordinate neutral ligands to low oxidation state indium centers are often hindered by disproportionation pathways that produce elemental indium and higher oxidation state species. In contrast, we find that reactions of the salt, InOTf (OTf=trifluoromethanesulfonate), with α-diimine ligands yielded intensely colored compounds with no evidence of decomposition. X-ray structural analysis of InOTf⋅(Mes) DAB(Me) ((Mes) DAB(Me) =N,N-dimesityl-2,3-dimethyl-diazabutadiene; 1) reveals a discrete molecular compound with a pyramidal coordination environment at the indium center, consistent with the presence of a stereochemically active lone pair of electrons on indium and a neutral diazabutadiene chelate ligand. The use of the less-electron-rich (Mes) DAB(H) ligand ((Mes) DAB(H) =N,N-dimesityl-diazabutadiene) engenders dramatically different reactivity and produces a metallopolymer (InOTf⋅(Mes) DAB(H) )∞ (2) linked via CC and InIn bonds. The difference in reactivity is rationalized by cyclic voltammetry and DFT studies that suggest more facile electron transfer from In(I) to the (Mes) DAB(H) and bis(aryl)acenaphthenequinonediimine (BIAN) ligands. Solution EPR spectroscopy indicates the presence of non-interacting ligand-based radicals in solution, whereas solid-state EPR studies reflect the presence of a thermally accessible spin triplet consistent with reversible CC bond cleavage.

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Section: Resultssupporting

confidence: 74%

“…find very little covalent interaction between diiminopyridine ligands and the indium centers in their dimpy complexes and proposed that a lower 5 s orbital contribution to the HOMO of the diiminopyridine complex is consistent with a more stable molecule 29. 35, 46…”

Section: Computational Investigationsmentioning

confidence: 99%

Non‐Innocent Ligand Effects on Low‐Oxidation‐State Indium Complexes

Allan

Cooper

Cowley

et al. 2013

Chemistry A European J

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“…While this work was in progress, a paper was published describing a voltammetric study of 1 d together with five variously substituted derivatives of the same scaffold 97. The paper, besides providing a review of the very few available voltammetric BIAN studies, which appear sparse and hardly reproducible, offers a reliable but only preliminary screening, in apparently non‐anhydrous acetonitrile, and consisting in simple peak comparison in global CV patterns, in terms of chemical reversibility and Hammett relationships.…”

Section: Resultsmentioning

confidence: 99%

Easy Entry into Reduced Ar‐BIANH₂ Compounds: A New Class of Quinone/Hydroquinone‐Type Redox‐Active Couples with an Easily Tunable Potential

Viganò

Ferretti

Caselli

et al. 2014

Chemistry A European J

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Ar-BIANH2 bearing different substituents on the aryl rings have been synthesized in high yield by reduction of the corresponding bis(aryl)acenaphthenequinonediimine (Ar-BIAN) compounds. The structure of p-CH3 C6 H4 -BIANH2 in the solid state was determined by X-ray diffraction. An exhaustive voltammetric investigation of the two parallel BIAN and BIANH2 series afforded a first rationalization of the redox properties of these molecules, highlighting their analogies with quinone/hydroquinone systems. Such analogies, in combination with the much more negative reduction potential range of Ar-BIAN compounds with respect to quinones, can afford to extend the range of reduction potentials so far obtainable by the use of quinones.

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“…We have recently begun to explore the use of Ar-BIAN ligands [83] as conjugated bpy surrogates, of which bis(4methoxyphenylimino)acenapthene (25), represents a prototypical example. [14a] Complexes of the form [(C ∧ N) 2 Ir- (25)] + piqued our interest as, unlike most other cationic iridium complexes, this class absorbed well out to 800 nm and thus showed potential in solar harvesting applications.…”

Section: Bis(arylamino)acenaphthene (Ar-bian)mentioning

confidence: 99%

A Comprehensive Survey of Cationic Iridium(III) Complexes Bearing Nontraditional Ligand Chelation Motifs

2013

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The useful optoelectronic properties of cationic iridium(III) complexes have been exploited in diverse applications, from visual displays to biological probes to analytical sensors. It is thus not surprising to note the increased recent efforts to document, understand, and ultimately control the photophysical and electrochemical properties of the archetypal cationic iridium(III) complex [(ppy) 2 Ir(bpy)] + , in which ppyH = 2phenylpyridine and bpy = 2,2Ј-bipyridine, and decorated versions thereof. Of the ligand architectures explored, the [a] Département 2986with N-heterocyclic carbenes (NHCs) are also included within the survey. We also wish to direct the reader to other recent review articles on other facets of Ir III chemistry, property evaluation, and applications. [1] This Review commences with a historical overview of iridium(III) chemistry, an account of the properties of iridium, and a comprehensive description of the photophysical properties of [(ppy) 2 Ir(bpy)] + (1), supported by a detailed DFT study. Following this perspective, the survey is then organized by type of heterocycle. The properties of these complexes are compared and contrasted with the archetype complex 1 and fluorinated congener [(dFppy) 2 Ir(bpy)] + (2), which in this Review act as benchmarks. Finally, optoelectronic data from complexes with structurally similar ligands are collated together to elucidate more clearly the salient structure-property relationships.

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Synthesis, UV–Vis and CV properties of a structurally related series of bis(Arylimino)acenaphthenes (Ar‐BIANs)

Cited by 43 publications

References 49 publications

Non‐Innocent Ligand Effects on Low‐Oxidation‐State Indium Complexes

Non‐Innocent Ligand Effects on Low‐Oxidation‐State Indium Complexes

Easy Entry into Reduced Ar‐BIANH₂ Compounds: A New Class of Quinone/Hydroquinone‐Type Redox‐Active Couples with an Easily Tunable Potential

A Comprehensive Survey of Cationic Iridium(III) Complexes Bearing Nontraditional Ligand Chelation Motifs

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Synthesis, UV–Vis and CV properties of a structurally related series of bis(Arylimino)acenaphthenes (Ar‐BIANs)

Cited by 43 publications

References 49 publications

Non‐Innocent Ligand Effects on Low‐Oxidation‐State Indium Complexes

Non‐Innocent Ligand Effects on Low‐Oxidation‐State Indium Complexes

Easy Entry into Reduced Ar‐BIANH2 Compounds: A New Class of Quinone/Hydroquinone‐Type Redox‐Active Couples with an Easily Tunable Potential

A Comprehensive Survey of Cationic Iridium(III) Complexes Bearing Nontraditional Ligand Chelation Motifs

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Easy Entry into Reduced Ar‐BIANH₂ Compounds: A New Class of Quinone/Hydroquinone‐Type Redox‐Active Couples with an Easily Tunable Potential