- Synthesis, characterization, and UV–visible study of some new photochromic formyl-containing 1′,3′,3′-trimethylspiro[chromene-2,2′-indoline] derivatives
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The spiropyran derivatives can exist in two forms, the closed-ring spiropyran form and the open-ring merocyanine (MC) form. The SP form could be converted into the MC form upon UV irradiation. In this work, some 1′,3′,3′-trimethylspiro[chromene-2,2′-indoline] derivatives containing the nitro and formyl groups are synthesized via the reaction of 1,3,3-trimethyl-2-methylene-5-nitroindoline with the corresponding salicylaldehyde derivatives. These compounds have different photochromic behaviors. The synthesized photochromic molecules are characterized by the FT-IR, 1H-NMR, and 13C-NMR spectroscopic techniques. In order to investigate the photochromic properties of these compounds, the UV–visible spectroscopic analyses of their methanolic solutions before and after exposure to a UV lamp (in the spectral range of 360–400?nm) are studied. Graphic abstract: [Figure not available: see fulltext.].
- Sepehr, Zeinalabedin,Nasr-Isfahani, Hossein,Mahdavian, Ali Reza,Amin, Amir Hossein
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p. 3061 - 3067
(2021/05/27)
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- 1,8-naphthalimide compound bonded with spiro-pyran, preparation method and applications thereof
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The invention discloses a 1,8-naphthalimide compound bonded with spiro-pyran, a preparation method and applications thereof. The 1,8-naphthalimide compound is prepared by modifying the N position of naphthalimide by photochromic spiro-pyran. The invention also discloses a specific preparation method of the compound. Before the compound is irradiated by light, the compound has a light yellow color. When the compound is activated by light, the compound gives off green fluorescence. When the compound is irradiated by light with a wavelength of 365 nm, the color of the compound is converted from yellow to orange red and the compound gives off brick red fluorescence. The compound is a light controllable photochromic and dual-component light controlled fluorescence molecular switch, is a bifunctional material, which has excellent performances of phototropy and photoluminescence, and has a wide application prospect.
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Paragraph 0032; 0033; 0034; 0035; 0036
(2016/12/16)
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- Colorimetric Cyanide Chemosensor Based on 1′,3,3′,4-Tetrahydrospiro[chromene-2,2′-indole]
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A new class of chemosensors based on the 1′,3,3′,4-tetrahydrospiro[chromene-2,2′-indole] ring system, which detects cyanide with high specificity, is described. These chemosensors show a distinct color change when treated with cyanide in acetonitrile solution buffered with sodium phosphate, and this procedure is not affected by the presence of other common anions. The chemisensors exhibit high sensitivity to low concentrations of cyanide, meeting the European Union water quality control criterion of sensitivity below 0.05 mg L-1, and show a very fast response within tens of seconds. The mechanism for detection is rationalized by the nucleophilic substitution of the phenolic oxygen atom at the indoline C-2 atom by the cyanide anion to form a stable indolylnitrile adduct and to generate the colored 4-nitrophenolate chromophore. These chemosensors can be synthesized by a simple procedure from commercially available starting materials.
- Dagiliene, Migle,Martynaitis, Vytas,Kri??iuˉniene, Vilija,Krik?tolaityte, Sonata,?a?kus, Algirdas
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p. 363 - 369
(2015/06/30)
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- Synthesis and spectral properties of polymethine-cyanine dye-nitroxide radical hybrid compounds for use as fluorescence probes to monitor reducing species and radicals
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Various hybrid compounds comprised of two types of nitroxide radicals and either a pentamethine (Cy5) or trimethine cyanine (Cy3) were synthesized. The nitroxide radicals were linked either via an ester-bond to one or two N-alkyl carboxyl-terminated groups of Cy5, or via two amido-bonds (aminocarbonyl or carbonylamino group) to the 5-position of the indolenine moieties of Cy5 and Cy3. Changes in fluorescence and ESR intensities of the hybrid compounds were measured before and after addition of Na ascorbate in PBS (pH 7.0) to reduce the radicals. Among the hybrid compounds synthesized, those that linked the nitroxide radicals via an aminocarbonyl residue at the 5-position of the indolenine moieties on Cy5 and Cy3 exhibited a 1.8- and 5.1-fold increase in fluorescence intensity with the reduction of the nitroxide segment by the addition of Na ascorbate, respectively. In contrast, fluorescence intensity was not enhanced in the other hybrid compounds. Thus, the hybrid compounds which exhibited an increase in fluorescent intensity with radical reduction can be used in the quantitative measurement of reducing species such as Fe2+ and ascorbic acid, and hydroxyl radicals. Because these hybrid compounds have the advantage of fluorescing at longer wavelengths-661 (Cy5) or 568 (Cy3) nm, respectively, they can be used to measure radical-reducing species or radicals either in solution or in vivo.
- Sato, Shingo,Tsunoda, Minoru,Suzuki, Minoru,Kutsuna, Masahiro,Takido-uchi, Kiyomi,Shindo, Mitsuru,Mizuguchi, Hitoshi,Obara, Heitaro,Ohya, Hiroaki
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scheme or table
p. 2030 - 2039
(2009/03/12)
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- Synthesis of some new substituted photochromic N,N′-bis(spiro[1- benzopyran-2,2′-indolyl])diazacrown systems with substituent control over ion chelation
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The reversible photochemical ion chelation of the newly synthesised substituted N,N′-bis(spiro[1-benzopyran-2,2′-indolyl])diazacrown systems 15a-c and the subsequent molecular electronic control of this process using appropriately placed substituent groups on the spiro-benzopyran skeleton is reported. The principle of molecular electronic control of ion chelation is demonstrated by comparing the behaviour of the newly synthesised nitro-substituted and pyrido-annulated spiro-benzopyran system 9b with that of the unsubstituted compound 9a. Electronic substituent control over ion chelation is then exemplified for the new N,N′-bis(5′-nitrospiro[1- benzopyran-2,2′-indolyl])diazacrown system 15c and further exemplified for the corresponding 5′-trifluoromethyl derivative 15b, which contains the photochemically more robust trifluoromethyl group. The crown system 15a, unsubstituted in the spiro-indole moiety, is also reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Roxburgh, Craig J.,Sammes, Peter G.
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p. 1050 - 1056
(2007/10/03)
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- Synthesis and structure of indoline spiropyrans of the coumarin series
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New indoline spiropyrans of the coumarin series were synthesized by the condensation of indoline and hydroxyformylcoumarin derivatives. Spiropyrans, viz., derivatives of 8-formyl-7-hydroxy-4-methylcoumarin and 5-formyl-6-hydroxy-4-methylcoumarin, under irradiation are transformed into open forms, which are recyclized in the dark. The compounds formed by the condensation of the indoline derivatives with 3-formyl-4-hydroxycoumarin have an open structure of the merocyanine dyes and are transformed into spiro forms neither in the dark nor under irradiation with the visible light.
- Traven,Miroshnikov,Chibisova,Barachevsky,Venidiktova,Strokach
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p. 2417 - 2424
(2007/10/03)
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- Agent for dyeing fibers comprising an indoline/indolium derivative
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The object of the present invention is an agent for dyeing fibers obtained by mixing two components and characterized in that one component (component A2) contains at least one carbonyl compound and the other component (component A1) contains at least one indoline derivative of formula (I) or a 3H-indoline derivative of formula (Ia) as well as a multicomponent kit for dyeing and later decolorizing fibers, said kit containing both an agent according to the invention for producing a coloration on the fiber and an agent for the reductive removal of said coloration.
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- SYNTHESE DE QUELQUES SPIRO ET SPIRO PHOTOCHROMIQUES. APPLICATION DE LA METHODOLOGIE DE LA RECHERCHE EXPERIMENTALE
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Some spiro I and spiro II substituted by different groups were synthesized in order to evaluate their photochromic properties and to optimize the preparation of spiroheterocyclic systems.In addition, some spiro III were also prepared as reference compounds.Their physical and spectroscopic characteristics (UV, 1H and 13C) were determined.A study using the experimental design methodology allowed to point out the most important factors for improving the reaction yields. KEYWORDS: Photochromism, spirooxazines, spiropyrans, synthesis, 1H NMR, experimental design methodology.
- Pottier, E.,Sergent, M.,Luu, R. Phan Tan,Guglielmetti, R.
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p. 719 - 740
(2007/10/02)
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- PHOTOCHROMISM. SYNTHESIS AND PROPERTIES OF INDOLINOSPIROBENZOTHIOPYRANS
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Novel photochromic compounds, indolinospirobenzothiopyrans, were prepared and their properties in polymer films were examined.The absorption bands of the colored form lie around 100 nm deeper in the long-wave region of the spectrum than are the case with the common spiropyrans.
- Arakawa, Sei'ichi,Kondo, Hirofumi,Seto, Jun'etsu
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p. 1805 - 1808
(2007/10/02)
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