Brooker's merocyanine

Brooker's merocyanine
Names
IUPAC name
1-methyl-4-[(oxocyclohexadienylidene)ethylidene]-1,4-dihydropyridine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.255.640
UNII
  • InChI=1S/C14H13NO/c1-15-10-8-13(9-11-15)3-2-12-4-6-14(16)7-5-12/h2-11H,1H3 Y
    Key: DBOHWMPKJCJANT-UHFFFAOYSA-N Y
  • InChI=1/C14H13NO/c1-15-10-8-13(9-11-15)3-2-12-4-6-14(16)7-5-12/h2-11H,1H3
    Key: DBOHWMPKJCJANT-UHFFFAOYAD
  • O=C\2\C=C/C(=C\C=C1\C=C/N(/C=C1)C)/C=C/2
Properties
C14H13NO
Molar mass 211.26 g/mol
Appearance Red crystals
Melting point 220 °C (428 °F; 493 K) (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Brooker's merocyanine (1-methyl-4-[(oxocyclohexadienylidene)ethylidene]-1,4-dihydropyridine, MOED) is an organic dye belonging to the class of merocyanines.

MOED is notable for its solvatochromic properties, meaning it changes color depending on the solvent in which it is dissolved.

As shown in the structural formula, MOED can be depicted using two resonance structures: neutral and zwitterionic. Research indicates that the zwitterionic structure is the major contributor to resonance hybrid when the compound exists in polar solvents such as water, and the neutral form when it exists in nonpolar solvents such as chloroform.