Metal-coordinated azoaromatics: Strategies for sequential azo-reduction, isomerization and application potential

Panda, Sanjib; Dhara, Suman; Singh, Anil Kumar; Dey, Sanchaita; Lahiri, Goutam Kumar

doi:10.1016/j.ccr.2022.214895

Cited by 22 publications

(24 citation statements)

References 211 publications

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“…[28,29] Contrary to the 3-, and 4-phenylazopyridines, the 2-phenylazopyridines usually coordinate in a bidentate mode utilizing the pyridine nitrogen along with one of the two azo-N atoms. [30] The photoisomerization in such cases is primarily hindered in those complexes due to the rigidity of the À N=NÀ unit upon Figure 2. Representative examples of metal complexes 1-7 incorporated with azopyridine as ligand.…”

Section: Azopyridines and Azobispyridinesmentioning

confidence: 99%

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Light‐Switchable Metal Complexes: Introducing Photoresponsive Behaviour Through Azoheteroarenes

et al. 2023

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Azoheteroarenes are emerging classes of photoswitches with versatile scaffolds that offer distinct features such as efficient photoisomerization, tunable stability of the photoswitched states, and bidirectional photoswitching. Moreover, the heteroatoms of such photoswitches exhibit coordination ability to bind to the metal centers. The resulting azoheteroarene‐based metal complexes can be designed and developed to tune various metal‐based properties towards intriguing applications such as in optics, magnetic properties, data storage applications, and catalysis. Despite the diverse utility of azopyridines in such contexts, other azoheteroarenes, particularly the state‐of‐the‐art five‐membered heterocycle‐based photoswitches, remain under‐explored. In this Review, we describe the diverse classes of azoheteroarene‐coordinated metal complexes reported in the literature and survey their photoswitching behaviour and applications. Furthermore, we identify potential azoheteroarene candidates for building photochrome‐coupled metal complexes and supramolecular architectures for maximizing the photo‐tuning of metal‐related properties.

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Section: Azopyridines and Azobispyridinesmentioning

confidence: 99%

“…[21][22][23][24][25] coordination. The À N=NÀ unit in such complexes is mostly utilized as an electron reservoir for initiating redox transformations [30] and photoisomerization of the resultant complexes were not explored in detail.…”

Section: Azopyridines and Azobispyridinesmentioning

confidence: 99%

Light‐Switchable Metal Complexes: Introducing Photoresponsive Behaviour Through Azoheteroarenes

et al. 2023

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“…Therefore, the incorporation of photoswitchable azobenzene-based amino acids, which change structure and polarity through cis/trans isomerization, should allow for photocontrol over coiled-coil assembly. Azobenzene motifs are well known for acting as biomolecular switches, and their utility has been extensively reviewed. − …”

Section: Introductionmentioning

confidence: 99%

Azobenzene-Based Amino Acids for the Photocontrol of Coiled-Coil Peptides

et al. 2023

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Coiled-coil peptides are high-affinity, selective, self-assembling binding motifs, making them attractive components for the preparation of functional biomaterials. Photocontrol of coiled-coil self-assembly allows for the precise localization of their activity. To rationally explore photoactivity in a model coiled coil, three azobenzene-containing amino acids were prepared and substituted into the hydrophobic core of the E3/K3 coiled-coil heterodimer. Two of the non-natural amino acids, APhe1 and APhe2, are based on phenylalanine and differ in the presence of a carboxylic acid group. These have previously been demonstrated to modulate protein activity. When incorporated into peptide K3, coiled-coil binding strength was affected upon isomerization, with the two variants differing in their most folded state. The third azobenzene-containing amino acid, APgly, is based on phenylglycine and was prepared to investigate the effect of amino acid size on photoisomerization. When APgly is incorporated into the coiled coil, a 4.7-fold decrease in folding constant is observed upon trans-to-cis isomerizationthe largest difference for all three amino acids. Omitting the methylene group between azobenzene and α-carbon was theorized to both position the diazene of APgly closer to the hydrophobic amino acids and reduce the possible rotations of the amino acid, with molecular dynamics simulations supporting these hypotheses. These results demonstrate the ability of photoswitchable amino acids to control coiled-coil assembly through disruption of the hydrophobic interface, a strategy that should be widely applicable.

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“…Since then, the investigation on MV compounds 4 has attracted great attention from chemists due to their particular structural, redox, spectroscopic, and charge transfer properties. 5 These make them potential in molecular electronics, 6 molecular magnetism, 7 molecular conductors, 8 non-linear optical materials, 9 and so on. The MV compounds were categorized by Robin and Day 10 into three classes depending on the extent of charge transfer or electron delocalization.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural and spectroscopic properties of a cyanido-bridged mixed-valence compound [Fe–NC–Ru–CN–Fe]

Liu

Xiong

et al. 2023

New J. Chem.

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Cyanide-bridged compounds trans-[Cp(dppe)FeII(NC)RuII(py)4(CN)FeII(dppe)Cp][PF6]2 (1, py = pyridine, dppe = bis (diphenylphosphino) ethane, Cp = cyclopentadienyl anion), trans-[Cp(dppe)FeII(NC)RuII(py)4(CN)FeIII(dppe)Cp][PF6]2 (2), trans-[Cp(dppe)FeIII(NC)RuII(py)4(CN)FeIII(dppe)Cp][PF6]2 (3) , trans-[Cp(dppe)FeII(NC)RuII(MeOpy)4(CN)FeII(dppe)Cp][PF6]2 ( 4, MeOpy = 4-methoxypyridine) and trans-[Cp(dppe)FeIII(NC)RuII(MeOpy)4(CN)FeII(dppe)Cp][PF6]3 (5)...

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Metal-coordinated azoaromatics: Strategies for sequential azo-reduction, isomerization and application potential

Cited by 22 publications

References 211 publications

Light‐Switchable Metal Complexes: Introducing Photoresponsive Behaviour Through Azoheteroarenes

Light‐Switchable Metal Complexes: Introducing Photoresponsive Behaviour Through Azoheteroarenes

Azobenzene-Based Amino Acids for the Photocontrol of Coiled-Coil Peptides

Synthesis and structural and spectroscopic properties of a cyanido-bridged mixed-valence compound [Fe–NC–Ru–CN–Fe]

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