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322547

Sigma-Aldrich

1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]naphth[2,1-b][1,4]oxazine]

≥98.0% (HPLC)

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Synonym(s):
Photorome I
Empirical Formula (Hill Notation):
C22H20N2O
CAS Number:
Molecular Weight:
328.41
MDL number:
PubChem Substance ID:
NACRES:
NA.23

assay

≥98.0% (HPLC)

mp

128-130 °C (lit.)

SMILES string

CN1c2ccccc2C(C)(C)C13Oc4ccc5ccccc5c4N=C3

InChI

1S/C22H20N2O/c1-21(2)17-10-6-7-11-18(17)24(3)22(21)14-23-20-16-9-5-4-8-15(16)12-13-19(20)25-22/h4-14H,1-3H3

InChI key

CQTRKDFIQFOAQV-UHFFFAOYSA-N

General description

1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]naphth[2,1-b][1,4]oxazine] (Photorome I) is an organic photochromic material that is used as a spirooxazine dye for use in molecular electronics. This dye changes to blue on irradiating with UV light.

Application

General applications of photochromic dye include: dosimetric materials, light controlling filters, recording films in printing processes, decorative paints, optical recording media and molecular electronic devices.1
Photorome I is a photochromic dye that can be used as a smart colorant for a variety of applications which include optical switches, printing materials, and ophthalmic lenses.

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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Photochromic wool fabrics from a hybrid silica coating.
Cheng T, et al.
Textile Res., 77(12), 923-928 (2007)
NMR studies of the structure of the photoinduced forms of photochromic spironaphthoxazines.
Delbaere S, et al.
J. Chem. Soc. Perkin Trans. II, 1499-1502 (1997)
Cellulose nanocrystals (CNC) as carriers for a spirooxazine dye and its effect on photochromic efficiency.
Sun B, et al.
Carbohydrate Polymers, 111(8), 419-424 (2014)
Interaction of a spirooxazine dye with latex and its photochromic efficiency on cellulosic paper.
Sun B, et al.
Carbohydrate Polymers, 95(1), 598-605 (2013)
Synthesis and properties of photochromic liquid-crystalline copolymers containing both spironaphthoxazine and cholesteryl groups.
Hattori H and Uryu T
Journal of Polymer Science Part A: Polymer Chemistry, 38(5), 887-894 (2000)

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