1,8-Diazafluoren-9-one

Last updated
1,8-Diazafluoren-9-one
Diazaflourenone.png
Names
Preferred IUPAC name
9H-Cyclopenta[1,2-b:4,3-b]dipyridin-9-one
Other names
DFO
9H-1,8-Diazafluoren-9-one
9H-Pyrido[3,2:3,4]cyclopenta[1,2-b]pyridin-9-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C11H6N2O/c14-11-9-7(3-1-5-12-9)8-4-2-6-13-10(8)11/h1-6H Yes check.svgY
    Key: FOSUVSBKUIWVKI-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C11H6N2O/c14-11-9-7(3-1-5-12-9)8-4-2-6-13-10(8)11/h1-6H
    Key: FOSUVSBKUIWVKI-UHFFFAOYAH
  • O=C1C3=C(C=CC=N3)C2=C1N=CC=C2
  • O=C3c1ncccc1c2c3nccc2
Properties
C11H6N2O2
Molar mass 198.181 g·mol−1
AppearanceYellow powder
Melting point 229–233 °C (444–451 °F; 502–506 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
NFPA 704 (fire diamond)
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

1,8-Diazafluoren-9-one (DFO) is an aromatic ketone first synthesized in 1950. It is used to find fingerprints on porous surfaces. [1] [2] It makes fingerprints glow when they are lit by blue-green light. [2]

DFO reacts with amino acids present in the fingerprint to form highly fluorescent derivatives. Excitation with light at ~470 nm results in emission at ~570 nm. [2]

Related Research Articles

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References

  1. Lewkowicz, Aneta; Baranowska, Karolina; Bojarski, Piotr; Józefowicz, Marek (2019). "Solvent dependent spectroscopic properties of fingerprint reagent - 1,8-Diazafluoren-9-one". Journal of Molecular Liquids. 285: 754–765. doi:10.1016/j.molliq.2019.04.110. S2CID   149852434.
  2. 1 2 3 Pounds, C. Anthony; Grigg, Ronald; Mongkolaussavaratana, Theeravat (1 January 1990). "The Use of 1,8-Diazafluoren-9-one (DFO) for the Fluorescent Detection of Latent Fingerprints on Paper. A Preliminary Evaluation". Journal of Forensic Sciences. 35 (1): 169–175. doi:10.1520/JFS12813J.