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273619

Sigma-Aldrich

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

98%

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]

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About This Item

Empirical Formula (Hill Notation):
C19H18N2O3
CAS Number:
1498-88-0
Molecular Weight:
322.36
EC Number:
216-102-5
MDL number:
MFCD00059175
UNSPSC Code:
12352103
PubChem Substance ID:
57648241
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

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
GHS07

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Spiropyrans and spirooxazines for memories and switches.
Berkovic G, et al.
Chemical Reviews, 100(5), 1741-1754 (2000)
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)
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)
Light-Driven Electrohydrodynamic Instabilities in Liquid Crystals.
Zhan Y, et al.
Advances in Functional Materials, 28(21), 1707436-1707436 (2018)
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