Brooker's merocyanine

Brooker's merocyanine
Names
	IUPAC name 1-methyl-4-[(oxocyclohexadienylidene)ethylidene]-1,4-dihydropyridine
Identifiers
CAS Number	23302-83-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	226778 ;
ECHA InfoCard	100.255.640
PubChem CID	258436;
UNII	K765RJZ7AS ;
CompTox Dashboard (EPA)	DTXSID70293129 ;
	InChI InChI=1S/C14H13NO/c1-15-10-8-13(9-11-15)3-2-12-4-6-14(16)7-5-12/h2-11H,1H3 Key: DBOHWMPKJCJANT-UHFFFAOYSA-N ; 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;
	SMILES O=C\2\C=C/C(=C\C=C1\C=C/N(/C=C1)C)/C=C/2;
Properties
Chemical formula	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). verify (what is ?) Infobox references

Brooker's merocyanine (1-methyl-4-[(oxocyclohexadienylidene)ethylidene]-1,4-dihydropyridine, MOED)^[1] 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.^[2]

^ Brooker, L.G.S.; Keyes, G.H.; Sprague, R.H.; VanDyke, R.H.; VanLare, E.; VanZandt, G.; White, F.L. (November 1951). "Studies in the cyanine dye series. XI. The Merocyanines". Journal of the American Chemical Society. 74 (11): 5326–5332. doi:10.1021/ja01155a095. link
^ "Fundamental Studies on Brooker’s Merocyanine", Morley et al., J. Am. Chem. Soc., 1997, 119 (42), 10192-10202 • doi:10.1021/ja971477m

[1] Brooker, L.G.S.; Keyes, G.H.; Sprague, R.H.; VanDyke, R.H.; VanLare, E.; VanZandt, G.; White, F.L. (November 1951). "Studies in the cyanine dye series. XI. The Merocyanines". Journal of the American Chemical Society. 74 (11): 5326–5332. doi:10.1021/ja01155a095. link

[2] "Fundamental Studies on Brooker’s Merocyanine", Morley et al., J. Am. Chem. Soc., 1997, 119 (42), 10192-10202 • doi:10.1021/ja971477m

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