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273619

Sigma-Aldrich

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

98%

Sinonimo/i:

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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1 G
CHF 182.00

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Cambia visualizzazione
1 G
CHF 182.00

About This Item

Formula empirica (notazione di Hill):
C19H18N2O3
Numero CAS:
Peso molecolare:
322.36
Numero CE:
Numero MDL:
Codice UNSPSC:
12352103
ID PubChem:
NACRES:
NA.23

CHF 182.00


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Livello qualitativo

Saggio

98%

Stato

solid

Punto di fusione

179-180 °C (lit.)

λmax

242 nm in ethanol

Stringa SMILE

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
PSXPTGAEJZYNFI-UHFFFAOYSA-N

Descrizione generale

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.[1][2][3] 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.[4] NitroBIPS possesses a higher quantum yield in comparison to other spiropyran molecules and dissolves in a variety of solvents.[5][6]

Applicazioni

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.[7] 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.[8] 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.[9]

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Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


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Slide 1 of 1

1 of 1

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
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)
Preparation, characterization, and application of optical switch probes.
Petchprayoon C and Marriott G
Current Protocols in Chemical Biology, 2(3), 153-169 (2010)
K Poots et al.
Annals of biomedical engineering, 14(3), 203-218 (1986-01-01)
A nonintrusive method for the visualization of pulsatile flow velocity profiles is described. The method is based on the use of a photochromic dye that is added to the fluid being studied and a nitrogen laser which excites the dye
Light-Driven Electrohydrodynamic Instabilities in Liquid Crystals.
Zhan Y, et al.
Advances in Functional Materials, 28(21), 1707436-1707436 (2018)

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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