119980-36-8Relevant articles and documents
Direct nitration reactions of photochromic spirooxazines
Zaichenko,Shiyonok,Kol'tsova,Marevtsev
, p. 83/[383]-89/[389] (2005)
A direct nitration of photochromic spirooxazines was carried out by three different methods. The molecular structure of main products was determined by NMR 1H and 13C spectra. The nitration mechanisms were proposed. It was shown that only nitration by mixture of nitric and sulfuric acids gives photochromic compounds with nitrogroup in aryloxazine ring.
SYNTHESIS AND PHOTOCHROMIC PROPERTIES OF SPIROANTHROOXAZINE
Vlasenko, T. Ya.,Zaichenko, N. L.,Lyubimov, A. V.,Marevtsev, V. S.,Cherkashin, M. I.
, p. 1375 - 1379 (1990)
1',3',3'-Trimethylspirooxazine> was synthesized.The compound has photochromic properties in solutions and in polymeric matrices.It was found from the spectral data that the colored form of the spiroanthrooxazine exists in a quinoid form and is characterized by a positive solvatochromic effect.
Photochromism and Thermochromism of Spiro in Normal and Reversed Micelles
Favaro, Gianna,Ortica, Fausto,Malatesta, Vincenzo
, p. 4099 - 4104 (1995)
Spectra, photochromism and thermochromism of a spiro and a spiro have been investigated in cationic (CTAB, hexadecyltrimethylammonium bromide) and non-ionic (TX-100) micellar solutions and in sodium bis-2-ethylhexylsulfosuccinate (AOT)/toluene/water inverted-micelles.The spectral shifts of the photomerocyanine colour band provided information on the location of the molecules in these systems.From photokinetic study of the colour-forming and colour-fading reactions, the quantum yield and bleaching constant were determined.The thermal equilibrium constant of the spiro was spectrophotometrically measured.Comparison of the results obtained in microheterogeneous systems with those determined in a homogeneous solution indicated that thermo- and photo-colourability increase in TX-100 and CTAB micelles and decrease in inverted micelles.
Phototriggered micromanufacturing using photoresponsive amorphous spirooxazine films
Ubukata, Takashi,Fujii, Shohei,Arimatsu, Kento,Yokoyama, Yasushi
body text, p. 14410 - 14417 (2012/09/11)
In this study, a series of spirooxazine molecules possessing bulky substituents was synthesized. These molecules readily formed amorphous glasses and their glass transition temperatures increased with the bulkiness of substitution. Their amorphous thin films exhibited apparent photochromism due to the spirooxazine-merocyanine isomerism and high durability to UV light in a nitrogen atmosphere. When the amorphous spirooxazine films were irradiated with spatially patterned UV light, surface relief gratings were produced because of the lateral material transfer from the shaded areas to the irradiated areas around their glass transition temperatures. Surface relief structure growth rate has a good relationship with the amount of photogenerated merocyanine formed at the irradiated area. A mechanism based on the diffusion of the spiro form for surface relief formation in this system has been proposed.
Coupling between Photochromism and Second-Harmonic Generation in Spiropyran- and Spirooxazine-Doped Polymer Films
Atassi, Yomen,Delaire, Jacques A.,Nakatani, Keitaro
, p. 16320 - 16326 (2007/10/02)
The photochemical ring opening of spiropyrans in polymethylmethacrylate (PMMA) host films in the presence of a high-voltage electric field (2-5 MV/cm) leads to a photo-orientation of photomerocyanines.Since photomerocyanines have rather high first-order hyperpolarizabilities, this photo-orientation leads to second-harmonic generation (SHG).The second-order susceptibility d33 of PMMA films doped with 6-nitro-1',3',3'-trimethylspiro (25percent w/w) has been measured at 10 pm/V.If a PMMA film doped with spiropyran and preoriented by corona poling at 90 deg C is irradiated in the UV, an SHG signal of photomerocyanine is also observed as a result of a memory effect of the orientation of spiropyran molecules.The photoswitching of this nonlinear optical property can be inverted by visible light irradiation.Only partially reversible switching is observed because of a gradual light-induced disorientation of photomerocyanine dipoles.Photochemical quantum yields of the spiropyranphotomerocyanine reaction have also been determined in PMMA for one system.Dipole moments and hyperpolarizabilities of closed and open forms have been calculated by semiempirical and finite field methods for an analogous system.
Synthesis and Photochromic Characteristics of 1,3-Dihydrospiropyrimidobenzoxazines> and 1,3-Dihydrospirothiazolobenzoxazines>
Tardieu, Pascale,Dubest, Roger,Aubard, Jean,Kellmann, Arlette,Tfibel, Francis,et al.
, p. 1185 - 1197 (2007/10/02)
Two new series of 1,3-dihydrospiro derivatives were synthesized, the 1,3-dihydrospiropyrimidobenzoxazines> 4-10 and the 1,3-dihydrospirothiazolobenzoxazines> 11-17.These series extend the available range of photochromic properties (rate constant of thermal bleaching, UV/VIS spectrum of the opened coloured form, and photocoloration yield), an interesting feature of variable-transmission materials.The synthesis of these compounds (Scheme 1) required the preliminary synthesis of intermediate β-hydroxy-α-nitrosoheterocycles 18 and 19 (Scheme 2).Important amounts of a coloured, non-photochromic, stable secondary product (see 20) were formed in the condensation in the spiro series.The photochromic characteristics of the new derivatives were determined using a flash-photolysis apparatus coupled to a fast-scanning spectrometer.The role of the heteroatoms in the oxazine moiety and the role of substituents in the indole moiety were investigated quantitatively through the study of the photochromic properties and the solvent effects.The presence of an S-atom gives rise to interesting properties which open up new prospects for synthesis and applications.
Sensibilisation du photochromisme de spirooxazines par transfert d'energie triplet-triplet
Eloy, D.,Escaffre, P.,Gautron, R.,Jardon, P.
, p. 897 - 914 (2007/10/02)
The present publication describes sensitized photocoloration by triplet-triplet energy transfer of some photochromic spirooxazines.The dominant reaction leading to the colored dye product B in the direct photolysis of the spirooxazine (SPO) in toluene involves the singlet excited state but the results obtained in this work show that both triplet and singlet states are involved in the color-forming reaction.We employed sensitizers of decreasing triplet energy in an attempt to locate the triplet level in the SPO.From the triplet energies of the sensitizers of the SPO color formation it can be concluded that the energy of the spirooxazine triplet state is about 212 kJ.mol-1.The camphorquinone (CQ) sensitizes the formation of B.This compound is particularly suitable for investigation of sensitized photocoloration of spirooxazines since it absorbs in a region of the spectrum where SPO does not absorb (λmax = 471 nm).Then, it is possible to extend the photochromic properties of the SPO to the visible region (λ 500 nm) for industrial applications.The absorption spectra of the colored form were determined for the direct and sensitized photolysis in toluene solutions.
NEW PHOTOCHROMIC 2H-1.4-OXAZINES AND SPIRO-2H-1.4-OXAZINES
Grummt, Ulrich-W.,Reichenbaecher, Manfred,Paetzold, Roland
, p. 3945 - 3948 (2007/10/02)
The synthesis and the photochemical behaviour of new 2H-1.4-oxazines and 3 new spiro-2H-1.4-oxazines is described.
