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Merck

273619

Sigma-Aldrich

1′,3′-Dihydro-1′,3′,3′-trimethyl-6-nitrospiro[2H-1-benzopyran-2,2′-(2H)-indole]

98%

Sinónimos:

1′,3′,3′-trimethyl-6-nitrospiro[chromene-2,2′-indole], 1,3,3-Trimethylindolino-6′-nitrobenzopyrylospiran; 1′,3′,3′-Trimethyl-6-nitrospiro[chromene-2,2′-indoline]

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About This Item

Fórmula empírica (notación de Hill):
C19H18N2O3
Número de CAS:
Peso molecular:
322.36
Número CE:
Número MDL:
Código UNSPSC:
12352103
ID de la sustancia en PubChem:
NACRES:
NA.23

Nivel de calidad

Ensayo

98%

Formulario

solid

mp

179-180 °C (lit.)

λmáx.

242 nm in ethanol

cadena SMILES

CN1c2ccccc2C(C)(C)C13Oc4ccc(cc4C=C3)[N+]([O-])=O

InChI

1S/C19H18N2O3/c1-18(2)15-6-4-5-7-16(15)20(3)19(18)11-10-13-12-14(21(22)23)8-9-17(13)24-19/h4-12H,1-3H3

Clave InChI

PSXPTGAEJZYNFI-UHFFFAOYSA-N

Descripción general

1′,3′-Dihydro-1′,3′,3′-trimethyl-6-nitrospiro(2H-1-benzopyran-2,2′-(2H)-indole)(NitroBIPS) is a photochromic biocompatible spiropyran molecule that has six nitro groups positioned at the benzopyran section. It has a colourless leuco spiropyran form(SP) and coloured trans-merocyanine form(MC) that exhibits absorption peaks in the ultraviolet and visible regions respectively. NitroBIPS possesses a higher quantum yield in comparison to other spiropyran molecules and dissolves in a variety of solvents.

Aplicación

NitroBIPS is used as a photochromic dye which can be incorporated in poly(vinylalcohol)(PVA) by electro-spinning to form PVA-spiropyran nanofibres. It has photo-responsive behaviour that may be useful in optical data storage applications. It can be used to dope liquid crystal to develop a coloured scattering device that is dual responsive and allows the initiation of electrohydrodynamic instabilities(EHDI). Addition of NitroBIPS can modify the transparency from 100% to 16%, providing a shielding effect which can be used for smart window applications. It may also be used to enhance the adhesion property of polystyrene(PS) on the glass substrate by improving the shear strength by a factor of 7.

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Los clientes también vieron

Photophysics, photochemistry, kinetics, and mechanism of the photochromism of 6'-nitroindolinospiropyran.
Lenoble C and Becker RS
The Journal of Physical Chemistry, 90(1), 62-65 (1986)
Spiropyrans and spirooxazines for memories and switches.
Berkovic G, et al.
Chemical Reviews, 100(5), 1741-1754 (2000)
M J Jozwiakowski et al.
Pharmaceutical research, 4(5), 398-401 (1987-10-01)
The title compound (6-NO2-BIPS) is adsorptiochromic, becoming colored upon adsorption to a polar surface. Powders of 6-NO2-BIPS adsorbed to silica gel or silicic acid are suspended in glycerin, and the absorption spectrum of the adsorbate is recorded by conventional absorption
Preparation, characterization, and application of optical switch probes.
Petchprayoon C and Marriott G
Current Protocols in Chemical Biology, 2(3), 153-169 (2010)
Direct structural determination of conformations of photoswitchable molecules by laser desorption-electron diffraction.
Andreas Gahlmann et al.
Angewandte Chemie (International ed. in English), 49(37), 6524-6527 (2010-08-18)

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