Novel photochromic spirocyclic compounds of thienopyrroline series: 1

Ширинян, Валерий З.; Besugliy, S. O.; Метелица, А. В.; Krayushkin, M. M.; Nikalin, D. M.

doi:10.1016/j.jphotochem.2007.01.026

Cited by 18 publications

(6 citation statements)

References 22 publications

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“…1b). 16 A linear correlation was seen between the wave numbers of the absorption maxima and the Brooker's red parameters, (w R ), indicating that the SPOD exhibits positive solvatochromism. The positive solvatochromism explains the weak polarity of the ground state of the MC form as observed previously for spirooxazine molecules.…”

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confidence: 89%

A tailored spirooxazine dimer as a photoswitchable binding tool

2009

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mentioning

confidence: 89%

A tailored spirooxazine dimer as a photoswitchable binding tool

2009

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“…Depending on the solvent polarity, the MC form has a tendency to prevail in one of several molecular structures: neutral, cyanine-like, and charge-separated zwitterionic . Based on this property, the MC isomer in solution has been studied for its potential use as an empirical indicator of solvent polarity of typical organic solvents, , aqueous binary solvent mixtures, and even ionic liquids. , Monolayers of spiropyran derivatives have been also bound to glass slides to study the polarity of their microenvironment . Although this approach offers interesting information about the interaction of the surface-bound spiropyran with its immediate environment, it is unpractical for studying solvent polarity of a system as a whole.…”

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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“…When the UV light is turned off, the solution gradually returns to the transparent state, implying a reversible nature of the SP−MC transformation. With the UV illumination, a broad absorption peak develops at around 590 nm and a minor shoulder appears at 420 nm, which are ascribed to excited state absorptions from merocyanine isomers . The pathway of SP-to-MC transition is shown in Figure , where the C−O bond cleavage has led to the generation of the biradicals in the intermediate that eventually transform to a more stable Zwitterion form of the MC molecule .…”

Section: Resultsmentioning

confidence: 99%

Photochromism and Photopolymerization Induced Mesophase Transitions in Mixtures of Spiropyran and Mesogenic Diacrylate

2010

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A phase diagram of a binary mixture of photochromic molecule (spiropyran) and mesogenic diacrylate monomer has been established by means of differential scanning calorimetry and polarized optical microscopy. Subsequently, a theoretical phase diagram has been calculated by self-consistently solving the combined Flory-Huggins free energy for isotropic mixing, Maier-Saupe free energy for nematic ordering, and phase field free energy for crystal solidification. The phase diagram thus obtained consists of various coexistence regions involving single-phase crystals, pure nematic, crystal + liquid, crystal + nematic, and crystal + crystal coexistence gaps. Under UV irradiation, both SP and SP/RM257 mixtures showed the lowering trend of the melting points, which may be attributed to the plasticization effect by the merocyanine isomers. When UV light is illuminated on the 2/98 SP/RM257 mixture for an extended period, mesogenic diacrylate in the mixtures gets polymerized, showing the permanent fixation of isotropic and nematic structures due to the network formation of RM257 caused by the biradicals in the merocyanine intermediate.

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Novel photochromic spirocyclic compounds of thienopyrroline series: 1

Cited by 18 publications

References 22 publications

A tailored spirooxazine dimer as a photoswitchable binding tool

A tailored spirooxazine dimer as a photoswitchable binding tool

Spiropyran Polymeric Microcapillary Coatings for Photodetection of Solvent Polarity

Photochromism and Photopolymerization Induced Mesophase Transitions in Mixtures of Spiropyran and Mesogenic Diacrylate

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