Surface-Enhanced Resonance Raman Studies of Spiropyrans (Bips and Derivatives)

Schneider, Siegfried; Grau, H.; Ringer, J.; Melzig, M.

doi:10.1080/10587259408037825

Cited by 14 publications

(22 citation statements)

References 4 publications

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“…solvents but can be observed in relatively concentrated alcoholic solutions in the dark . It is formed in the reaction ().…”

Section: Resultsmentioning

confidence: 99%

“…Absorption spectra and photochromic properties of SP/MC in alcohol solutions have been reported . The long‐wavelength band in the absorption spectrum of SP has λ max = 295 nм with extinction coefficient ε 295 = 6.0 × 10 3 M −1 cm −1 (see Figure a).…”

Section: Resultsmentioning

confidence: 99%

“…Al salts of strong acids undergo hydrolysis in the water‐containing alcoholic solutions leading to acidic media. It is known that strong acids are able to protonate MC of SP and essentially stabilize it that way . Therefore, it is of interest to compare the reactivity of Al 3+ and H + towards SP/MC.…”

Section: Introductionmentioning

confidence: 99%

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New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

Levin

Belikov

Левина

et al. 2019

J of Physical Organic Chem

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Ultraviolet‐visible (UV‐vis) absorption, flash photolysis, and 1H and 13C NMR spectroscopy were used to investigate the mechanism of formation and structure of complexes in the 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (SP, also well known as BIPS) with Al3+ (inorganic salts) in ethanol (EtOH), methanol (MeOH), and in aqueous MeOH solutions. A labile (equilibrium constants ≤ 5000 M−1) complex of SP and Al3+ with broad absorption band in the UV‐vis with λmax = 380 nm appeared promptly in the presence of an excess of Al3+. The slow formation of a stable complex (SC) between Al3+ and two merocyanine (MC) forms of SP with an intensive absorption band at λmax = 430 nm is observed with a yield of 1.0 upon keeping the solutions of these two compounds at constant concentration ratio [Al3+] ≥[SP]/2 in the dark. The rate constants of such SC formation were close to the corresponding rate constant of the transformation of SP into MC in the dark (5.0×10−5‐1×10‐3 s‐1, depending upon the solvent). The photolysis of the SC with visible light (λ > 400 nm) results in the total conversion of the SC into SP. The SC forms promptly after the addition of Al3+ at concentrations of the same order as those of MC. This method allows detection of [Al3+] to concentrations as low as 50 nM. The kinetics and thermodynamic parameters of the SP and MC reactions and of their complex formation with Al3+ are discussed.

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“…solvents but can be observed in relatively concentrated alcoholic solutions in the dark . It is formed in the reaction ().…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

Levin

Belikov

Левина

et al. 2019

J of Physical Organic Chem

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“…On the other hand, SP-2 produced a violet solution in NA (λ abs,max SP-2/NA = 564 nm) with very little absorption in the region around 430 nm, indicating selective formation of the non-protonated MC state as a consequence of the less basic character of its o-methoxy-p-nitrophenolate group. [41][42][43] Finally, mixtures of the MC and MCH + forms were obtained for NA solutions of SP-1 and SP-4, which showed different spectral contributions from both species owing to their distinct acid-base properties: while major formation of MC was observed for SP-1 also bearing a low-basicity p-nitrophenolate group upon isomerization (red colour, λ abs,max…”

Section: Tunable Reverse Photochromism Of Spiropyrans In Nonanoic Acidmentioning

confidence: 99%

“…via hydrogen-bond interactions) or convert it into the protonated form MCH + through acid-base reactions. [41][42][43] All these strategies have been explored to obtain reverse photochromism with spirocompounds in liquid media (e.g. protic solvents, [37][38] ionic liquids, [44][45] solutions of acids [46][47] or metal ions [28][29][30][31][32][33][34][35][36] ) as well as in bulk or micro/nanostructured solid systems, which are eventually more relevant for practical applications (e.g.…”

Section: Introductionmentioning

confidence: 99%

Solid Materials with Tunable Reverse Photochromism

Julià-López

Ruiz‐Molina

Hernando

et al. 2019

ACS Appl. Mater. Interfaces

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Herein we report on a novel, straightforward and universal strategy to achieve solid materials with highly tunable reverse photochromism. This was accomplished by means of commercially available spiropyran dyes, which can produce different types of stable merocyanine states (i.e. non-protonated and protonated forms) displaying distinct reverse photochromic properties (i.e. colours and colouration rates). To finely control the concentration ratio of these species and, as such, tailor the optical performance of the photochromes, we exploited their differential interaction with surrounding media of distinctive nature (i.e. non-volatile protic and aprotic polar solvents). In this way, solutions displaying different photochromic responses were prepared for individual spiropyrans without requiring chemical derivatization, an approach that can be generalized to other spiro dyes with distinct acid-base properties. To transfer this behaviour to the solid state, core-shell capsules of these solutions were prepared, which were then used as ink materials for the fabrication of flexible polymeric films with unprecedented tunability of their photochromic properties that can be employed as rewritable multicoloured devices.

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Temperature‐Controlled Switchable Photochromism in Solid Materials

et al. 2016

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A novel strategy to achieve thermally switchable photochromism in solid materials is reported, which relies on the preparation of polymeric core–shell capsules containing solutions of photochromic dyes in acidic phase‐change materials. Upon changing the phase (solid or liquid) of the encapsulated medium, one of the two photochromic states of the system is selectively stabilized on demand, allowing for reversible interconversion between direct and reverse photochromism when thermally scanning through the melting temperature of the phase‐change material. This strategy, which does not require the addition of external agents or chemical modification of the dyes, proved to be general for different spiropyran photochromes and to be applicable to the fabrication of a variety of functional materials by simply embedding the capsules obtained into a solid matrix of choice.

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Surface-Enhanced Resonance Raman Studies of Spiropyrans (Bips and Derivatives)

Cited by 14 publications

References 4 publications

New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

Solid Materials with Tunable Reverse Photochromism

Temperature‐Controlled Switchable Photochromism in Solid Materials

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Surface-Enhanced Resonance Raman Studies of Spiropyrans (Bips and Derivatives)

Cited by 14 publications

References 4 publications

New stable colored complex of Al3+ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

New stable colored complex of Al3+ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

Solid Materials with Tunable Reverse Photochromism

Temperature‐Controlled Switchable Photochromism in Solid Materials

Contact Info

Product

Resources

About

New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)

New stable colored complex of Al³⁺ with 1',3',3'‐trimethylspiro[2H‐1‐benzopyran‐2,2'‐indoline] (BIPS)