Spiropyran salts and their neutral precursors: synthesis, crystal structure, photochromic transformations in solutions and solid state

Yurieva, E. A.; Алдошин, С. М.

doi:10.1515/oph-2015-0004

Cited by 5 publications

(3 citation statements)

References 20 publications

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“…These results indicate that photochromic reactivity of [ PSP ]X crystals depends on their packing structure, which governs the molecular motion upon photoisomerization. One of the reasons for exhibiting crystalline-state photochromism in [ PSP ]I has been reported as looser packing by separating each [ PSP ] + due to being the ionic salts . The reaction cavity calculation allows a quantitative analysis of the reaction cavity volume necessary for crystalline-state photochromism.…”

Section: Results and Discussionmentioning

confidence: 99%

Solid-State Photochromism of Salts of Cationic Spiropyran with Various Anions: A Correlation between Reaction Cavity Volumes and Reactivity

Funasako

Ason

Takebayashi

et al. 2019

Crystal Growth & Design

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The salts of cationic spiropyran with various anions ([PSP]X; X = I, NO3, SCN, BF4, ClO4, PF6, CF3BF3, OTf, and BPh4) were prepared, and their crystalline-state photochromism and crystal structures were investigated. Four salts (X = I, NO3, SCN, and BPh4) exhibited photochromism in the crystalline state. In all the crystals, the cations and anions are alternately arranged to form mixed-stacked columns, with the exception of [PSP]BPh4, which has a grid-like arrangement of the anion. Most of the salts exhibit a disorder of cations. For all the salts, the reaction cavity between the pyridinium ring of the cation and the adjacent anion was determined based on their crystal structures. The reaction cavity volumes in the photochromic salts were larger than those in other salts (>8.9 Å3). These results demonstrate that the crystalline-state photochromism depends on the size of the reaction cavity necessary for structural isomerization. Additionally, shear stress also induces the isomerization of the cations of all the salts in the solid state.

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Section: Results and Discussionmentioning

confidence: 99%

Solid-State Photochromism of Salts of Cationic Spiropyran with Various Anions: A Correlation between Reaction Cavity Volumes and Reactivity

Funasako

Ason

Takebayashi

et al. 2019

Crystal Growth & Design

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“…However, the aforementioned pyridinium and quinolinium derived SPPs are characterized by the location of absorption maxima at about 550-595 nm and have no remarkable fluorescence. [32][33][34] Fortunately, NIR-absorption and NIR-photoluminescence can be conferred on SPPs by an extension of the conjugation chain. Derivatives containing the vinyl-3H-indolium fragment are excellent candidates for combining the photoreactivity of SPPs and optical characteristics of classical HMCys.…”

Section: Introductionmentioning

confidence: 99%

“…In addition, some types of anions allow to create single molecule photomagnets, [27–29] polychromogenic compounds [30] and ionic liquids with light controllable polarity [31] based on SPPs . However, the aforementioned pyridinium and quinolinium derived SPPs are characterized by the location of absorption maxima at about 550–595 nm and have no remarkable fluorescence [32–34] …”

Section: Introductionmentioning

confidence: 99%

Structure–Properties Correlations in the Range of Cationic Spiropyrans as Analogues of Cyanine Dyes

Kozlenko,

Pugachev,

Ozhogin

et al. 2024

ChemistrySelect

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Recently the need for smart materials has been extremely growing, and the development of materials with appropriate characteristics has become one of the main challenges. Heptamethine cyanine dyes are widely used in theranostics and photovoltaics due to their remarkable optical properties. However, they are characterized by “rigid” non–changable properties. The main aim of the current study is to unveil correlation between structure and optical properties in the range of vinyl‐3H‐indolium substituted spiropyrans, which can be considered as the closest analogs of heptamethine cyanines with the photocontrolable optical and fluorescent properties. The effects of substitution in indoline and 2H‐chromene cycles, as well as anion change are under the study. To achieve this goal, a series of spiropyran iodides and perchlorates with methyl, methoxy substituents or fluorine atom in position 6′, as well as a conjugated vinyl‐3H‐indolium fragment in position 8′, were synthesized. The structure of the compounds was carefully studied using SC XRD, NMR, IR and mass spectroscopy. Then, studies on absorption and photoluminescence characteristics, as well as photochromic behavior were carried out.

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Spiropyrans: molecules in motion

Kozlenko

Pugachev

Ozhogin

et al. 2021

Chem Heterocycl Comp

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Spiropyran salts and their neutral precursors: synthesis, crystal structure, photochromic transformations in solutions and solid state

Cited by 5 publications

References 20 publications

Solid-State Photochromism of Salts of Cationic Spiropyran with Various Anions: A Correlation between Reaction Cavity Volumes and Reactivity

Solid-State Photochromism of Salts of Cationic Spiropyran with Various Anions: A Correlation between Reaction Cavity Volumes and Reactivity

Structure–Properties Correlations in the Range of Cationic Spiropyrans as Analogues of Cyanine Dyes

Spiropyrans: molecules in motion

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