3,3-Diphenyl-3H-naphthopyran

Chemical compound From Wikipedia, the free encyclopedia

3,3-Diphenyl-3H-naphthopyran is an organic compound that is the parent of several related naphthopyrans. This family of compounds are used as photochromic dyes in ophthalmic glasses.[1] The compound is a colorless solid.

Quick facts Names, Identifiers ...
3,3-Diphenyl-3H-naphthopyran
Names
Preferred IUPAC name
3,3-Diphenyl-3H-naphtho[2,1-b]pyran
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.111.746 Edit 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 mass 334.418 g·mol−1
Appearance colorless solid
Melting point 158–160 °C (316–320 °F; 431–433 K)
Hazards
GHS labelling:
GHS09: Environmental hazard
Warning
H411
P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactions

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

Upon exposure to UV-radiation, the pyran 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

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