Solvatochromic behavior of non-activated indolinobenzospiropyran 6-carboxylates in aqueous binary solvent mixtures. Part II1

Keum, Sam‐Rok; Roh, Se-Jung; Ahn, Su-Mi; Lim, Sabina; Kim, Sung-Hoon; Koh, Kwangnak

doi:10.1016/j.dyepig.2006.02.013

Cited by 30 publications

(22 citation statements)

References 15 publications

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“…22 Depending on the solvent polarity, the MC form has a tendency to prevail in one of several molecular structures: neutral, cyaninelike, and charge-separated zwitterionic. 23 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 24,25 , aqueous binary solvent mixtures 26 and even ionic liquids. 27,28 Monolayers of spiropyran derivatives have been also bound to glass slides to study the polarity of their microenvironment 29 .…”

Section: Scheme 1 Photochromic Behaviour Of Monomeric Spiropyransmentioning

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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Section: Scheme 1 Photochromic Behaviour Of Monomeric Spiropyransmentioning

confidence: 99%

Spiropyran Polymeric Microcapillary Coatings for Photodetection of Solvent Polarity

et al. 2013

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“…The spiropyrans' solvatochromism [6,33] was used to optimize the solvents for the NMR-characterization in order to obtain pure spectra of the closed or the corresponding open species, respectively. …”

Section: A C C E P T E D Accepted Manuscriptmentioning

confidence: 99%

Diversely halogenated spiropyrans - Useful synthetic building blocks for a versatile class of molecular switches

Schulz‐Senft

Gates²,

Sönnichsen

et al. 2017

Dyes and Pigments

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Spiropyrans are dyes that can be reversibly switched to a highly colored merocyanine form by a number of stimuli such as light, mechanical force or temperature. To make use of these molecules, there is a requirement to functionalize them appropriately. Herein we report a library of spiropyrans bearing two (pseudo)halide functional groups on either half of the molecule. Such halide substituents are valuable, because they themselves may be used as reactive sites in cross-coupling reactions, for example. Different combinations of halides, for which different reactivities in cross-coupling reactions may be expected, will facilitate selective consecutive cross-coupling reactions and condensations. Data concerning the UVvis characteristics, the photostationary equilibria of the materials as well as the half-life of the merocyanine forms in solution are presented.

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“…Spiroindloino compound is an obtained by condensation of Fisher's base (1.6; R=alkyl) with salicyaldehyde (1.7.). Another route of synthesis may be with indolinium compound bearing different N-alkyl groups (1.6; R=alkyl) and different ring substituents; chemical reaction of synthesis is shown in Figure 4 by alkylation of a 2-methylindole to obtain (1.8.; R=alkyl) (Keum et al, 2007). The obtained pink-brown solution is refluxed for 2 h. The reaction mixture evaporated to a small volume in an air draft.…”

Section: Synthesis Of Spiroindolinobenzopyransmentioning

confidence: 99%

From Murex Purpura to Sensory Photochromic Textiles

Đurašević¹,

Osterman²,

Sutlović³

2011

Textile Dyeing

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Solvatochromic behavior of non-activated indolinobenzospiropyran 6-carboxylates in aqueous binary solvent mixtures. Part II1

Cited by 30 publications

References 15 publications

Spiropyran Polymeric Microcapillary Coatings for Photodetection of Solvent Polarity

Spiropyran Polymeric Microcapillary Coatings for Photodetection of Solvent Polarity

Diversely halogenated spiropyrans - Useful synthetic building blocks for a versatile class of molecular switches

From Murex Purpura to Sensory Photochromic Textiles

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