Electrochemical Characterization of Spiropyran Structures

Armendáriz-Vidales, Georgina; Martínez‐González, Eduardo; Hernández-Melo, Denhy; Tiburcio, Jorge; Frontana, Carlos

doi:10.1016/j.proche.2014.12.039

Cited by 7 publications

(6 citation statements)

References 10 publications

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“…The increased electron density at the indoline moiety from the metal fragment is also apparent from the more cathodic potential of 23 and 24 . Additional evidence for the indoline first oxidation is the irreversible nature of the first oxidation of 25 mirroring similar anodic responses of spiropyrans. − A discussion of the electrochemical behavior of the control complexes 31 – 33 can be found in the Supporting Information.…”

Section: Resultsmentioning

confidence: 84%

“…This second oxidation process is irreversible in the voltammogram of 19 (Figure S12), with several cathodic return waves observed, indicative of an ECE mechanism . This second oxidation process is tentatively assigned to the indoline moiety of the spiropyran. − …”

Section: Resultsmentioning

confidence: 94%

“…47−51 Complex 17 also exhibits an irreversible reduction event at −1.76 V associated with the nitro group. 47 An putative ECE mechanism is also observed on a repeat scan of this reduction process with several new anodic events appearing (Figure S7).…”

Section: ■ Introductionmentioning

confidence: 88%

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Multistate Switching of Some Ruthenium Alkynyl and Vinyl Spiropyran Complexes

Jago,

Walkey,

Gaschk

et al. 2023

Inorg. Chem.

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To study the switching properties of photochromes, we undertook the synthesis and characterization of several ruthenium organometallic complexes of the type [Ru(Cp*)(dppe)(CC-SP)] or [Ru(CO)(dppe)(PPh3)Cl(CHCH-SP)], where SP = spiropyran. The spectroscopic and electrochemical properties of the complexes were determined by careful cyclic voltammetric and spectroelectrochemical experiments. Whereas the mononuclear alkynyl ruthenium complexes undergo one-electron oxidations localized over the metal alkynyl moiety, the oxidation of the mononuclear vinyl ruthenium complexes is centered on the indoline moiety of the spiropyran. Through these studies, we demonstrate access to several stable redox states, in addition to switching states attained via acidochromism and/or photoisomerization.

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Section: Resultsmentioning

confidence: 84%

Section: Resultsmentioning

confidence: 94%

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Multistate Switching of Some Ruthenium Alkynyl and Vinyl Spiropyran Complexes

Jago,

Walkey,

Gaschk

et al. 2023

Inorg. Chem.

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“…To further shed light on the mechanism of Cu(II) reduction in the presence of MOF photochromic linkers, we employed cyclic voltammetry (CV) studies with the support of literature reports. ,,− As a first step, we performed CV measurements on BPMTC and TNDS in the dark and under constant UV irradiation (λ ex = 365 nm). For photochromic BPMTC (5.0 mM in acetonitrile (ACN), vs SCE, Figure S34), we observed no redox behavior in the dark; however, under UV irradiation, an irreversible oxidation wave at E ox = 0.63 V was evident.…”

Section: Resultsmentioning

confidence: 99%

Stimuli-Modulated Metal Oxidation States in Photochromic MOFs

et al. 2022

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Tuning metal oxidation states in metal–organic framework (MOF) nodes by switching between two discrete linker photoisomers via an external stimulus was probed for the first time. On the examples of three novel photochromic copper-based frameworks, we demonstrated the capability of switching between +2 and +1 oxidation states, on demand. In addition to crystallographic methods used for material characterization, the role of the photochromic moieties for tuning the oxidation state was probed via conductivity measurements, cyclic voltammetry, and electron paramagnetic resonance, X-ray photoelectron, and diffuse reflectance spectroscopies. We confirmed the reversible photoswitching activity including photoisomerization rate determination of spiropyran- and diarylethene-containing linkers in extended frameworks, resulting in changes in metal oxidation states as a function of alternating excitation wavelengths. To elucidate the switching process between two states, the photoisomerization quantum yield of photochromic MOFs was determined for the first time. Overall, the introduced noninvasive concept of metal oxidation state modulation on the examples of stimuli-responsive MOFs foreshadows a new pathway for alternation of material properties toward targeted applications.

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“…Specifically in electrochemical systems, their use is based on structural changes and charge variations rather than redox reactions. Note that spiropyran–merocyanine molecules are not redox active, if extreme potentials are not applied , thus being different from the majority of photoswitchable electrochemical systems discussed above. In other words, photocontrolled electrochemical processes with their participation are not related to the oxidation‐reduction of the spiropyran–merocyanine groups themselves, but originate from their conformational changes and electrostatic charge interactions affecting other components of electrochemical systems.…”

Section: Spiropyran‐merocyanine‐based Photoelectrochemical Switchesmentioning

confidence: 99%

Modified Electrodes and Electrochemical Systems Switchable by Light Signals

Katz¹

2018

Electroanalysis

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This article is an overview of extensive research efforts in many laboratories in the last two decades in the area of light‐switchable electrochemical systems and modified electrodes. Electrochemical reactions, including electrocatalytic and bioelectrocatalytic processes, have been reversibly activated and inhibited upon irradiation with light at different wavelengths. In order to realize these light activated or inhibited processes, the electrodes or/and reacting molecules were functionalized with photoisomerizable molecules including various derivatives of diarylethene, phenoxynaphthacenequinone, azobenzene and spiropyran/merocyanine. Photochemical reactions of these species resulted in change of their redox activity, conformation and electrical charge. All these changes affected electrode surfaces or (bio)molecules resulting in switching ON‐OFF corresponding (bio)electrochemical processes. Various systems based on different light‐controlled reactions are reviewed and discussed with specific examples and with many illustrating figures. Possible extensions of the research area and future applications are briefly overviewed in the conclusion section. The present comprehensive review is addressed to a broad scientific community, including newcomers to the area.

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Electrochemical Characterization of Spiropyran Structures

Cited by 7 publications

References 10 publications

Multistate Switching of Some Ruthenium Alkynyl and Vinyl Spiropyran Complexes

Multistate Switching of Some Ruthenium Alkynyl and Vinyl Spiropyran Complexes

Stimuli-Modulated Metal Oxidation States in Photochromic MOFs

Modified Electrodes and Electrochemical Systems Switchable by Light Signals

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