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Sigma-Aldrich

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

98%

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Synonym(s):
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]
Empirical Formula (Hill Notation):
C19H18N2O3
CAS Number:
Molecular Weight:
322.36
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23

assay

98%

form

solid

mp

179-180 °C (lit.)

λmax

242 nm in ethanol

SMILES string

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

InChI key

PSXPTGAEJZYNFI-UHFFFAOYSA-N

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This Item
740845SML1229D134406
vibrant-m

SML1229

2′,3′-cGAMP sodium salt

assay

98%

assay

97%

assay

≥98% (HPLC)

assay

97%

λmax

242 nm in ethanol

λmax

-

λmax

-

λmax

-

form

solid

form

solid

form

powder

form

solid

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

General description

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.

Application

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.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
V N Yurechko
The International journal of artificial organs, 16(3), 146-150 (1993-03-01)
A new method for the investigation of hydrodynamics of artificial heart valves is presented. It is a method of flow visualisation. The photochromic flow visualization method is based on activation of color tracers in originally colorless photochromic solutions by pulse
Excited-state dynamics of spiropyran-derived merocyanine isomers.
Wohl CJ and Kuciauskas D
The Journal of Physical Chemistry B, 109(47), 22186-22191 (2005)
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

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