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Lucigenin





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Lucigenin is an aromatic compound used in areas which include chemiluminescence. Its chemical name is bis-N-methylacridinium nitrate. It exhibits a bluish-green fluorescence.

Lucigenin
Names
Preferred IUPAC name

10,10′-Dimethyl[9,9′-biacridine]-10,10′-diium dinitrate

Other names

Bis-N-methylacridinium nitrate; N,N′-Dimethyl-9,9'-bisacridinium nitrate

Identifiers

CAS Number

3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.295 Edit this at Wikidata

PubChem CID

CompTox Dashboard (EPA)

  • InChI=1S/C28H22N2.2NO3/c1-29-23-15-7-3-11-19(23)27(20-12-4-8-16-24(20)29)28-21-13-5-9-17-25(21)30(2)26-18-10-6-14-22(26)28;2*2-1(3)4/h3-18H,1-2H3;;/q+2;2*-1 checkY

    Key: KNJDBYZZKAZQNG-UHFFFAOYSA-N checkY

  • InChI=1/C28H22N2.2NO3/c1-29-23-15-7-3-11-19(23)27(20-12-4-8-16-24(20)29)28-21-13-5-9-17-25(21)30(2)26-18-10-6-14-22(26)28;2*2-1(3)4/h3-18H,1-2H3;;/q+2;2*-1

    Key: KNJDBYZZKAZQNG-UHFFFAOYAH

  • C[n+]1c2ccccc2c(c3c1cccc3)c4c5ccccc5[n+](c6c4cccc6)C.[N+](=O)([O-])[O-].[N+](=O)([O-])[O-]

Properties

Chemical formula

 C28H22N4O6
Molar mass 510.506 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

checkY verify (what is checkY☒N ?)

Infobox references

It is used as a probe for superoxide anion in biology, for its chemiluminescent properties.

Synthesis

edit

It may be prepared from acridone.

There's also a route from toluene:[1]

 
Synthesis of Lucigenin from Toluene. References in the image description.

References

edit
  1. ^ Amiet, R. Gary (February 1982). "The preparation of lucigenin: An experiment with charm". Journal of Chemical Education. 59 (2): 163–164. doi:10.1021/ed059p163. ISSN 0021-9584. Retrieved 20 November 2023.


 

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.

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    Last edited on 28 November 2023, at 07:31  





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