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3,3-Diphenyl-3H-naphthopyran

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(Redirected fromNaphthopyran)
3,3-Diphenyl-3H-naphthopyran
Names
Other names
3,3-diphenyl-3H-naphtho[2,1-b]pyran
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.111.746Edit this at Wikidata
EC Number
  • 609-998-8
  • InChI=1S/C25H18O/c1-3-10-20(11-4-1)25(21-12-5-2-6-13-21)18-17-23-22-14-8-7-9-19(22)15-16-24(23)26-25/h1-18H
    Key: UBNNJVRNPJVYBU-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C2(C=CC3=C(O2)C=CC4=CC=CC=C43)C5=CC=CC=C5
Properties
C25H18O
Molar mass334.418 g·mol−1
Appearancecolorless solid
Melting point158–160 °C (316–320 °F; 431–433 K)
Hazards
GHS labelling:[1]
GHS09: Environmental hazard
Warning
H411
P273,P391,P501
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

3,3-Diphenyl-3H-naphthopyran is anorganic compound that is the parent of several related naphthopyrans. This family of compounds are used asphotochromic dyes inophthalmic glasses.[1] The compound is a colorless solid.

Synthesis and reactions

[edit]

The synthesis of naphthopyrans starts with2-naphthol.[2]

Upon exposure to UV-radiation, thepyran ring opens. The products, "photomerocyanines", are yellow to red dark colored.[3]

Isomers of photomerocyanines derived from UV-radiation of 3,3-diphenyl-3H-naphthopyran.

References

[edit]
  1. ^Lötzsch, Detlef; Eberhardt, Volker; Rabe, Christian (2016). "Chromogenic Materials".Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–26.doi:10.1002/14356007.t07_t01.ISBN 978-3-527-30673-2.
  2. ^Pozzo, Jean-Luc; Samat, André; Guglielmetti, Robert; Dubest, Roger; Aubard, Jean (1997). "Synthesis and Photochromic Behaviour of Naphthopyrans, Pyranoquinolines, Pyranoquinazolines and Pyranoquinoxalines".Helvetica Chimica Acta.80 (3):725–738.doi:10.1002/hlca.19970800310.
  3. ^Delbaere, Stéphanie; Luccioni-Houze, Barbara; Bochu, Christophe; Teral, Yannick; Campredon, Mylène; Vermeersch, Gaston (1998). "Kinetic and structural studies of the photochromic process of 3H-naphthopyrans by UV and NMR spectroscopy".Journal of the Chemical Society, Perkin Transactions 2 (5):1153–1158.doi:10.1039/A800906F.
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