- The synthesis and spectroscopic properties of novel, photochromic indolinobenzospiropyran-based homopolymers prepared via ring-opening metathesis polymerization
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Three types of novel photochromic indolinobenzospiropyran-based homopolymers were prepared via the ring-opening metathesis polymerization of the strained bicyclic indolinobenzospiropyran derivative. The homopolymers were soluble in common organic solvents and displayed unusually high polydispersity as determined by gel permeation chromatographic analysis. UV-visible absorption spectroscopy analysis in solution revealed that the appealing photochromic behaviour exhibited by the respective monomers was retained.
- Keum, Sam-Rok,Ahn, Su-Mi,Roh, Se-Jung,Ma, So-Young
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- Synthesis of spiropyran with methacrylate at the benzopyran moiety and control of the water repellency and cell adhesion of its polymer film
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Stimuli-responsive materials have been actively researched over the past few decades. Among such materials, spiropyran is one of the most attractive compounds because the structure and polarity of the material are dramatically changed after photo irradiation, unlike other materials. In this work, we designed and synthesized a spiropyran derivative (SpMA) with a methacryloyl group on the nitrobenzene ring of a spiropyran skeleton. The UV spectra of the newly synthesized SpMA showed the photo-isomerization of spiropyran. The maximum absorption wavelength (λmax) of SpMA was 616 nm in n-hexane, a nonpolar solvent, although λmax of SpMA was 532 nm in methanol, a polar protic solvent, which resulted in an 84 nm blue-shift. SpMA was successfully polymerized by ruthenium (Ru)-catalyzed living radical polymerization. Poly(SpMA) (PSpMA) was then spin-coated on a PET substrate in order to control the surface properties of water repellency and cell adhesion. The water repellency was decreased approximately 10° under UV irradiation, because of the polarity change of PSpMA caused by photo-isomerization from the spiropyran (SP) type to the merocyanine (MC) type. In addition, NIH3T3 cells were spread only on 6% of the surface of the PSpMA thin film after UV irradiation compared with no UV irradiation. The polarity change of PSpMA by photo-isomerization is also believed to be the reason for this behavior. As a result, we successfully synthesized a photo-controllable cell culture scaffold.
- Ajiro, Hiroharu,Ando, Tsuyoshi,Murase, Nobuo
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p. 1489 - 1495
(2020/03/06)
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- Nanoliter-scale, regenerable ion sensor: Sensing with a surface functionalized microstructured optical fibre
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The first nanoliter-scale regenerable ion sensor based on a microstructured optical fibre (MOF) is reported. The air holes of the MOF are functionalized with a monoazacrown bearing spiropyran to give a switchable sensor that detects lithium ions down to 1
- Heng, Sabrina,Nguyen, Mai-Chi,Kostecki, Roman,Monro, Tanya M.,Abell, Andrew D.
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p. 8308 - 8317
(2013/09/02)
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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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- MRI probes of membrane potential
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The invention provides methods and compositions for molecular resonance imaging of membrane potential. The compositions comprise an indicator moiety attached through an optional linker to a macrocycle component that binds a lanthanide. The indicator moiet
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- Crystal and solution structures of photochromic spirobenzothiopyran. First full characterization of the meta-stable colored species
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Full elucidation for stable, colorless, and meta-stable colored structures of a new spirobenzothiopyran has been achieved both in the solid state and in a solution. 1′,3′,3′-Trimethyl-6-nitrospiro[(2H)-1-benzothiopyran-2, 2′-indoline] with an ester group as a substituent at the 8-position of 1-sp shows photochromism. The blue-green colored species resulted from UV irradiation (365 nm) in one minute and spontaneously bleaches within one minute in acetone and methanol at 27 °C. UV exposure (365 nm) of 1-sp in methanol for 3 h at room temperature results in the growth of deep blue needlelike single crystals of the open form of spirobenzothiopyran, photomerocyanine 1-pmc, whose structures in the solid state and in solution were obtained unambiguously. The X-ray structural analysis of 1-pmc revealed the molecular structure of the zwitterionic photomerocyanine with s-trans,s-trans conformation. 1-pmc is soluble to polar solvents and thermally returns to 1-sp. In the DMSO solution, 1-pmc is found to return slowly to 1-sp (1-pmc gave only 18% of 1-sp for 30 min at 22 °C). The detailed NMR studies in DMSO-d6 including COSY and NOE techniques as well as isotope labeling of the compound showed the structure with s-trans,s-cis conformation in a solution.
- Hirano, Masafumi,Osakada, Kohtaro,Nohira, Hiroyuki,Miyashita, Akira
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p. 533 - 540
(2007/10/03)
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- Spiropyran compounds and optically active spiropyran compounds and their use
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The present invention relates to a spiropyran compound represented by the formula (1); an optically active spiropyran compound wherein an asymmetric center is introduced on a spirocarbon; and optical functional materials using these compounds, STR1 wherei
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- Spiropyran compounds
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The present invention provides a spiropyran compound represented by the formula STR1 wherein R1 is alkyl having 1 to 20 carbon atoms or aralkyl, R2, R3, R4 and R5 are the same or different and are each a hydrogen atom, alkyl having 1 to 6 carbon atoms, aryl or aralkyl, alkoxyl having 1 to 5 carbon atoms, halogen atom, cyano, trichloromethyl, trifluoromethyl or nitro, R6 and R7 are the same or different and are each a hydrogen atom, alkyl having 1 to 6 carbon atoms, aryl or aralkyl, halogen atom, cyano or nitro, X is an oxygen atom or sulfur atom, Y is Se or (CH3)2 C3)2 C. The spiropyran compound of the present invention itself is usable as a material such as recording material, photosensitive material, optical filter or decorative material. The present compound can further be homopolymerized or copolymerized with other polymerizable compound into a high polymer spiropyran compound for application to optical devices or dynamic devices.
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- INDOLINOSPIROBENZOPYRAN DERIVATIVE
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[Object] The object of the invention is to provide a novel compound suited for use as a thermochromic and photochromic material. [Constitution] The invention relates to a crystal of an indolinospirobenzopyran derivative for use as a photomerocyanine, said derivative being represented by the general formula [wherein R1 means an alkyl group of 1 to 20 carbon atoms, an aralkyl group, a methacryloxymethyl group or a methacryloxyethyl group; R2, R3, R4 and R5 may be the same or different and each means a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, an aryl group, an aralkyl group, an alkoxy group of 1 to 5 carbon atoms, a halogen atom, a cyano group or a nitro group; R6 and R7 may be the same or different and each means a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, an aryl group, an aralkyl group, a halogen atom, a cyano group or a nitro group; R8 means a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 5 carbon atoms, a chloromethyl group, a methacryloxymethyl group or a vinyl group; and Y means an oxygen atom or a sulfur atom.]
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- CRYSTAL COMPRISING INDOLINOSPIROBENZOTHIOPYRAN DERIVATIVE AND RING-OPENING ISOMER THEREOF
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A novel compound suitable for use as a piezochromic material, namely a crystal comprising an indolinospirobenzothiopyran derivative represented by general formula (I) and a ring-opening isomer thereof, and a process for the production thereof, wherein R1 represents C1 to C20 alkyl, aralkyl, methacryloxymethyl or methacryloxyethyl; R2, R3, R4, R5 R6 and R7 represent each hydrogen, etc.; and R8 represents hydrogen, methacryloxymethyl, etc.
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- Synthesis and Metastable Structure of New Photochromic Spiroindolinobenzothiopyrans
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Photochromic spiroindolinobenzothiopyrans having a methacryloxymethyl group have been prepared and their colored forms were demonstrated to be a zwitterionic structure on the basis of the spectroscopic data.
- Hirano, Masafumi,Miyashita, Akira,Nohira, Hiroyuki
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p. 209 - 212
(2007/10/02)
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- Synthesis and Photochemical Properties of Novel Spirobenzoselenazolinobenzopyrans
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5-Methoxy-3-methyl-6'-nitrospirobenzoselenazolinobenzopyrans have been newly prepared and their reversible structure changes induced by light were characterized by spectroscopic studies.Their stable colored-forms were identified as 5-methoxy-3-methylbenzoselenazolenium-2-trans-(5'-nitrostyryl-2'-oxide) being a zwitterionic structure.
- Hirano, Masafumi,Miyashita, Akira,Shitara, Hiroaki,Nohira, Hiroyuki
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p. 1873 - 1876
(2007/10/02)
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