273619

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]
• 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

Properties

• Quality Level: 100
• 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

Description

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.[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]

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.[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]

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves