Oxazolone‐Based Photoswitches: Synthesis and Properties

Blanco-Lomas, Marina; Funes‐Ardoiz, Ignacio; Campos, Pedro J.; Sampedro, Diego

doi:10.1002/ejoc.201300641

Cited by 38 publications

(20 citation statements)

References 34 publications

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“…Local absorption maxima in the 330–350 nm range are common for oxazolone compounds, but extension of the heterocycle’s conjugation system results in a bathochromic shift (44), as observed for Oxa A in Mbn, which is adjacent to an additional ketone group in lieu of the N-terminal amine. Copper binding by the oxazolones both quenches fluorescence emission intensity and alters their absorption maxima (43).…”

Section: Methanobactinsmentioning

confidence: 94%

Chalkophores

Kenney

Rosenzweig

2018

Annu. Rev. Biochem.

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Copper-binding metallophores, or chalkophores, play a role in microbial copper homeostasis that is analogous to that of siderophores in iron homeostasis. The best-studied chalkophores are members of the methanobactin (Mbn) family—ribosomally produced, posttranslationally modified natural products first identified as copper chelators responsible for copper uptake in methane-oxidizing bacteria. To date, Mbns have been characterized exclusively in those species, but there is genomic evidence for their production in a much wider range of bacteria. This review addresses the current state of knowledge regarding the function, biosynthesis, transport, and regulation of Mbns. While the roles of several proteins in these processes are supported by substantial genetic and biochemical evidence, key aspects of Mbn manufacture, handling, and regulation remain unclear. In addition, other natural products that have been proposed to mediate copper uptake as well as metallophores that have biologically relevant roles involving copper binding, but not copper uptake, are discussed.

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Section: Methanobactinsmentioning

confidence: 94%

Chalkophores

Kenney

Rosenzweig

2018

Annu. Rev. Biochem.

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“…These results demonstrate that the main isomer of the switch can be tuned by choosing the appropriate irradiation wavelength. Further studies on a series of derivatives of oxazolone compounds revealed that a bathochromic shift in the absorption spectrum occurs when the methyl group at R 1 position is replaced with a phenyl group 48. Substitution with a para or ortho methoxy group at R 2 position results in absorption spectra in the visible range, which is desirable for use as a photoswitch in biological systems.…”

Section: Recent Applications Of the Photoisomerizable Azobenzene Smentioning

confidence: 99%

Weiterentwicklung und Charakterisierung eines Spinning‐Disc‐Reaktors nach dem Rotor‐Stator‐Prinzip

Haseidl

Schuh

Hinrichsen

2015

Chemie Ingenieur Technik

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Ein vielversprechendes Reaktorkonzept zur Prozessintensivierung stellt der Spinning-Disc-Reaktor (SDR) dar. Im Rahmen dieser Arbeit wurde der Reaktor zu einem SDR nach dem Rotor-Stator-Prinzip weiterentwickelt, wobei die rotierende Scheibe von einem zylindrischen Stator umgeben ist. Zum besseren Verständnis der Vorgänge in dem dünnen, stark gescherten Flüssigkeitsfilm wird die Mikrovermischung mithilfe der Villermaux-Dushman-Reaktion untersucht. Darüber hinaus erfolgt eine systematische Untersuchung der Einflussparameter auf die Stoffübergangsvorgänge bei der heterogen katalysierten Glucose-Oxidation. Hierzu wird ein Pt/C-Katalysator auf der Scheibe immobilisiert. Further Development and Characterization of a Rotor-Stator Spinning Disc ReactorThe spinning disc reactor (SDR) is a promising reactor concept for process intensification. For this work, the reactor is modified into a rotor-stator SDR by placing the disc in a cylindrical shroud. The Villermaux-Dushman reaction is applied to investigate the effect of high shear forces on mixing efficiency of liquid flow in the narrow reactor cavity. Subsequently, this allows the methodical examination of mass transfer properties for heterogeneously catalyzed reactions. The glucose oxidation with dissolved oxygen in water is studied as model reaction employing a Pt/C catalyst immobilized on the rotating disc.

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“…4-Arylidene-5(4 H )-oxazolones are closely related to imidazolones, which are precursors of the former ( Figure 1 b). Unsaturated oxazolones are also luminescent and they have additional remarkable photophysical properties that include two-photon absorption (TPA), up-conversion, nonlinear optical properties and unique behavior as molecular switches [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Orthopalladated Complexes of 4-Aryliden-5(4H)-oxazolones from the Kaede Protein: Synthesis and Characterization

et al. 2021

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The goal of the work reported here was to amplify the fluorescent properties of 4-aryliden-5(4H)-oxazolones by suppression of the hula-twist non-radiative deactivation pathway. This aim was achieved by simultaneous bonding of a Pd center to the N atom of the heterocycle and the ortho carbon of the arylidene ring. Two different 4-((Z)-arylidene)-2-((E)-styryl)-5(4H)-oxazolones, the structures of which are closely related to the chromophore of the Kaede protein and substituted at the 2- and 4-positions of the arylidene ring (1a OMe; 1b F), were used as starting materials. Oxazolones 1a and 1b were reacted with Pd(OAc)2 to give the corresponding dinuclear orthometalated palladium derivates 2a and 2b by regioselective C–H activation of the ortho-position of the arylidene ring. Reaction of 2a (2b) with LiCl promoted the metathesis of the bridging carboxylate by chloride ligands to afford dinuclear 3a (3b). Mononuclear complexes containing the orthopalladated oxazolone and a variety of ancillary ligands (acetylacetonate (4a, 4b), hydroxyquinolinate (5a), aminoquinoline (6a), bipyridine (7a), phenanthroline (8a)) were prepared from 3a or 3b through metathesis of anionic ligands or substitution of neutral weakly bonded ligands. All species were fully characterized and the X-ray determination of the molecular structure of 7a was carried out. This structure has strongly distorted ligands due to intramolecular interactions. Fluorescence measurements showed an increase in the quantum yield (QY) by up to one order of magnitude on comparing the free oxazolone (QY < 1%) with the palladated oxazolone (QY = 12% for 6a). This fact shows that the coordination of the oxazolone to the palladium efficiently suppresses the hula-twist deactivation pathway.

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Oxazolone‐Based Photoswitches: Synthesis and Properties

Cited by 38 publications

References 34 publications

Chalkophores

Chalkophores

Weiterentwicklung und Charakterisierung eines Spinning‐Disc‐Reaktors nach dem Rotor‐Stator‐Prinzip

Fluorescent Orthopalladated Complexes of 4-Aryliden-5(4H)-oxazolones from the Kaede Protein: Synthesis and Characterization

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