3,3-Diphenyl-3H-naphthopyran

3,3-Diphenyl-3H-naphthopyran

Names
Other names 3,3-diphenyl-3H-naphtho[2,1-b]pyran
Identifiers
CAS Number	4222-20-2  Y
3D model (JSmol)	Interactive image
ChemSpider	2359442
ECHA InfoCard	100.111.746
EC Number	609-998-8
PubChem CID	3104870
CompTox Dashboard (EPA)	DTXSID0063365
InChI 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
SMILES C1=CC=C(C=C1)C2(C=CC3=C(O2)C=CC4=CC=CC=C43)C5=CC=CC=C5
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H411
Precautionary statements	P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.

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

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.