Structures and photo- and thermochromic properties of spiropyrans of the 2-oxaindan series with polycondensed chromene fragments

Алдошин, С. М.; Lokshin, Vladimir; Rezonov, A. N.; Volbushko, N. V.; Shelepin, N. E.; Knyazhanskii, M. I.; Atovmyan, L. O.

doi:10.1007/bf00486903

Cited by 10 publications

(2 citation statements)

References 4 publications

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“…These compounds were obtained through condensation of the corresponding heterocyclic salts with 4-formyl:5-hydroxy-2,3-tetramethylenebenzofuran (26) (Scheme 8) under previously described conditions (27)(28)(29)(30). The spiropyrans present two heterocyclic parts linked together by a common tetrahedral sp3 carbon atom.…”

Section: Methodsmentioning

confidence: 99%

Furo-fused 2H-chromenes: synthesis and photochromic properties

Pozzo¹,

Samat²,

Guglielmetti³

et al. 1996

Can. J. Chem.

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New photochromic chromenes annulated with a furan ring have been synthesized. Thus, suitable heterocyclic phenols react with different propargylic alcohols in acidic medium to give the corresponding ethers, which cyclize into benzopyrans by thermal Claisen rearrangement. This synthetic approach was found to lead to a mixture of linear and angular chromenes that is strictly related to the nature of the phenol. However, regiospecificity could be obtained by reacting P-phenylcinnamaldehyde, in refluxing aprotic nonpolar solvents, with titanium(1V) salts of the former phenols. Electrocyclization of intermediately generated o-quinoid structures occurs on the a position towards the heterocyclic junction. All compounds exhibit photochromic behavior at room temperature. Furo-fused benzopyrans are particularly interesting with respect to naphthopyran parents in view of the bathochromically shifted and broadened absorption spectra of photoinduced forms. This trend is confirmed by the spectral data of several heterocyclospiro(7H-furo[3,2-fl chromenes). The achievable color depends significantly on the relative position of annulation on the chromenic moiety and substitution on the sp3 carbon atom.Key words: photochromisrn, heterocycle, regiospecificity, 2H-chromene, furan.

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Section: Methodsmentioning

confidence: 99%

Furo-fused 2H-chromenes: synthesis and photochromic properties

Pozzo¹,

Samat²,

Guglielmetti³

et al. 1996

Can. J. Chem.

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“…For light sensitive polymers, the most easily discernible or distinguishable features are photosensitive groups, such as azobenzenes, coumarins, spiropyrans, or salicylidene . Generally, there are no hard and fast requirements for the quantity of photosensitive groups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Temperature and Light Sensitive Copolymers with Controlled Aggregation during Phase Transitions

Ding

Zhang

et al. 2019

Macro Chemistry & Physics

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Two thermosensitive copolymers of acrylates (PMP/PEP) and a thermo/light sensitive copolymer of acrylate with acrylamide (PMABz) are synthesized via a ring‐opening reaction and subsequent radical polymerization using a facile one‐pot method. The lower critical solution temperature (LCST) of PMP and PEP shows a dependence on the content of the structural unit and can be easily tuned to 18–35 °C by mercaptoethanol‐mediated control of the molecular weight. The isomerization of PMABz can be reversibly induced by alternating irradiation at 365 nm to produce the cis form and at 254 nm to produce the trans form. The LCST of cis‐PMABz (40.3 °C) is significantly higher than that of trans‐PMABz (37.8 °C) because of its higher hydrophilicity. Furthermore, the particle size of aggregated PMABz can be controlled from 665 nm (for the cis form) to 996 nm (for the trans form) during the heating run. After quenching the PMABz solution, PMABz particles have repeating patterns, such as leaf veins or hollow containers, indicating their potential applicability.

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Thermochromism of Organic Compounds

Samat

Lokshin

Topics in Applied Chemistry

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Structures and photo- and thermochromic properties of spiropyrans of the 2-oxaindan series with polycondensed chromene fragments

Cited by 10 publications

References 4 publications

Furo-fused 2H-chromenes: synthesis and photochromic properties

Furo-fused 2H-chromenes: synthesis and photochromic properties

Synthesis of Temperature and Light Sensitive Copolymers with Controlled Aggregation during Phase Transitions

Thermochromism of Organic Compounds

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