Anodic oxidation mechanism of a spiropyran

Preigh, Michael J.; Stauffer, Mark T.; Lin, Fu-Tyan; Weber, Stephen G.

doi:10.1039/ft9969203991

Cited by 39 publications

(46 citation statements)

References 12 publications

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“…(4.1 g, 23.6 mmol). 1 7,9,9,9a-tetramethyl-2,3,9,9a-tetrahydrooxazolo[3,2-a]indole (6) Compound 6 (4.1 g, 23.6 mmol) and bromoethanol (3.25 g, 26.0 mmol) were dissolved in 40 mL acetonitrile and the mixture heated at reflux for 3 h. The solvent was removed in vacuo and 40 mL pentane was added to the residue. After 5 min sonication the product was cooled to -10 °C and the pentane was removed by decantation.…”

Section: 335-tetramethyl-3h-indole (5)mentioning

confidence: 99%

Oxidative electrochemical aryl C–C coupling of spiropyrans

Ivashenko

Herpt²,

Rudolf³

et al. 2013

Chem. Commun.

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Section: 335-tetramethyl-3h-indole (5)mentioning

confidence: 99%

Oxidative electrochemical aryl C–C coupling of spiropyrans

Ivashenko

Herpt²,

Rudolf³

et al. 2013

Chem. Commun.

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“…This yields the coloured MC isomer that can return to the SP form by ring closing under visible light irradiation or in the dark through thermal relaxation 7,15 . Despite the potential applications of photochromic spiropyrans, earlier studies mainly focused on evaluating the utility of monomeric SP systems in solution [16][17][18] .…”

Section: Introductionmentioning

confidence: 99%

Spiropyran Polymeric Microcapillary Coatings for Photodetection of Solvent Polarity

et al. 2013

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Fused silica micro-capillaries were functionalised with spiropyran-polymer brushes using surface-initiated ring-opening metathesis polymerisation. Based on the inherited spiropyran properties, the functionalised capillaries were successfully used to photo-identify solvents of different polarity when passing through the micro-capillary in continuous flow. In the present study, six different solvents (toluene, tetrahydrofuran, acetone, acetonitrile, ethanol and methanol) can be easily detected while passing through the modified micro-capillary by simply irradiating a portion of it with UV light (365 nm). This converts the closed spiropyran moiety to the open merocyanine form and as a consequence, the micro-capillary gains a distinct colour and spectral response depending on the polarity of the solvent. The rate of ring opening of the spiropyran-polymer brushes coatings has been determined in-situ in the presence of different 2 solvents, showing that the coloration rate is also influenced by the solvent polarity and therefore can be used as an additional parameter for solvent sensing.

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“…Irradiation of spiropyrans (SP, Figure 1) with near-UV light 3 or electro-oxidation 4 induces heterolytic cleavage of the spiro carbon-oxygen bond to produce ring-opened structures (MC, Figure 1), represented as two resonance forms, one merocyanine-like and the other quinoidal. The intense absorption in the visible region of the open form MC has led to the advance study of spiropyrans in photochromic, 5 molecular optoelectronic 6 optobioelectronic fields, 7 and chemical sensing.…”

Section: Introductionmentioning

confidence: 99%

A Multiswitchable Poly(terthiophene) Bearing a Spiropyran Functionality: Understanding Photo- and Electrochemical Control

et al. 2011

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An electroactive nitrospiropyran-substituted polyterthiophene, 2-(3,3′′-dimethylindoline-6′-nitrobenzospiropyranyl)ethyl 4,4′′-didecyloxy-2,2′:5′,2′′-terthiophene-3′-acetate, has been synthesized for the first time. The spiropyran, incorporated into the polymer backbone by covalent attachment to the alkoxyterthiophene monomer units, leads to multiple coloured states as a result of both electrochemical isomerization of the spiropyran moiety to merocyanine forms as well as electrochemical oxidation of the polyterthiophene backbone and the merocyanine substituents. While electrochemical polymerization of the terthiophene monomer could occurs without the apparent oxidation of the spiropyran, the subsequent electrochemistry is complex and clearly involves this substituent. In order to understand this complex behaviour, the first detailed electrochemical study of the oxidation of the precursor spiropyran, 1-(2-hydroxyethyl)-3,3-dimethylindoline-6'-nitrobenzospiropyran, was undertaken, showing that, in solution, an irreversible electrochemical oxidation of the spiropyran occurs leading to reversible redox behaviour of at least two merocyanine isomers. With these insights, an extensive electrochemical and spectroelectrochemical study of the nitrospiropyran-substituted polyterthiophene films reveals an initial irreversible electrochemical oxidative ring opening of the spiropyran to oxidized merocyanine. Subsequent reduction and cyclic voltammetry of the resulting nitromerocyanine-substituted polyterthiophene film gives rise to the formation of both merocyanine π-dimers or oligomers and π-radical cation dimers, between polymer chains. Although merocyanine formation is not electrochemically reversible, the spiropyran can be photochemically regenerated, at least in part, through irradiation with visible light. SEM and AFM images support the conclusion that the bulky spiropyran substituent is electrochemically isomerizes to the planar merocyanine moiety affording a smoother polymer film. The conductivity of the freestanding polymer film was found to be 0.4 S cm -1 .3

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Anodic oxidation mechanism of a spiropyran

Cited by 39 publications

References 12 publications

Oxidative electrochemical aryl C–C coupling of spiropyrans

Oxidative electrochemical aryl C–C coupling of spiropyrans

Spiropyran Polymeric Microcapillary Coatings for Photodetection of Solvent Polarity

A Multiswitchable Poly(terthiophene) Bearing a Spiropyran Functionality: Understanding Photo- and Electrochemical Control

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