Isomerization and changes of the properties of spiropyrans by mechanical stress: advances and outlook

Pugachev, A. D.; Муханов, Е. Л.; Ozhogin, Ilya V.; Kozlenko, Anastasia S.; Metelitsa, Anatoly V.; Lukyanov, B. S.

doi:10.1007/s10593-021-02881-y

Cited by 24 publications

(3 citation statements)

References 104 publications

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“…Mechanochromism is a general term that comprises changes in the color of a substance during its crushing, shredding, grinding, friction (tribochromism), application of high pressure (piezochromism), or sonication, both in the solid state and in solutions [28,193].…”

Section: Mechanochromismmentioning

confidence: 99%

“…Spiropyrans of the indoline series are in focus as the most promising and the most studied representatives of multi-sensitive spirocyclic compounds, which can be switched by a number of external stimuli, including light, temperature, pH, presence of metal ions, mechanical stress, and other compounds. The spectral properties and parameters of their phototransformations strongly depend on the substituents present in the molecule; therefore, a directed change in their nature enables the search for new photochromes with desired properties and various stimulus-responsive structural elements [4,5,17,[21][22][23][24][25][26][27][28].…”

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confidence: 99%

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5′-Substituted Indoline Spiropyrans: Synthesis and Applications

et al. 2023

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Section: Mechanochromismmentioning

confidence: 99%

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confidence: 99%

5′-Substituted Indoline Spiropyrans: Synthesis and Applications

et al. 2023

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“…This process, in the case of influence of light radiation with various spectral composition on spiropyrans, is called photochromism [1]. Photochromic spiropyrans can be used as easily tunable molecular switches in various advanced industry of science and technology [2][3][4].…”

Section: Doi: 101134/s1070363221070069mentioning

confidence: 99%

Structure and Properties of 1,3,3-Trimethyl-6′-chlorospiro[indoline-2,2′-2H-chromene]

et al. 2021

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Indoline spiropyran containing an σ-acceptor chlorine atom in 6′ position of the 2H-chromene part of the molecule was synthesized and studied. The use of 1,2,3,3-tetramethyl-3H-indolium perchlorate as a starting compound made it possible to achieve higher product yields as compared to previous studies. The molecular structure of the compound was established by single crystal X-ray diffraction analysis. The features of the crystal structure and intermolecular interactions were investigated using CrystalExplorer17 software package. The photochromic behavior in acetonitrile solution was studied for the first time. It was found that the merocyanine form of spiropyran is characterized by an absorption maximum at 592 nm, which is 37 nm closer to the range of the “biological window” in comparison with the nitro-substituted analog.

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Stereodivergent Synthesis of Spiroaminals via Chiral Bifunctional Hydrogen Bonding Organocatalysis

Gayen,

Sar,

Ghorai

2024

Angewandte Chemie

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Spiroaminals represent novel structural motifs prevalent in diverse natural products and biologically active molecules. Achieving their enantioselective synthesis is a highly desirable and challenging task in synthetic endeavors due to their intricate molecular frameworks. Herein, we accomplished the first stereodivergent construction of spiroaminals using chiral bifunctional organocatalyzed intramolecular 1,2‐addition followed by an oxa‐Michael addition cascade in a high atom and step economical pathway. A proper modulation of the cinchona‐derived squaramide catalysts efficiently provided access to all the possible stereoisomers with high yield, diastereoselectivity, and excellent enantioselectivity while displaying a broad substrate tolerance. Additionally, we validated the scalability of the reaction and demonstrated the synthesis of variable spiroaminal scaffolds, confirming the viability of our protocol.

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Isomerization and changes of the properties of spiropyrans by mechanical stress: advances and outlook

Cited by 24 publications

References 104 publications

5′-Substituted Indoline Spiropyrans: Synthesis and Applications

5′-Substituted Indoline Spiropyrans: Synthesis and Applications

Structure and Properties of 1,3,3-Trimethyl-6′-chlorospiro[indoline-2,2′-2H-chromene]

Stereodivergent Synthesis of Spiroaminals via Chiral Bifunctional Hydrogen Bonding Organocatalysis

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