Merocyanine

Merocyanines are a class of polymethine dyes which are clearly defined by set structural properties. Merocyanines belong to the group of dyes referred to as functional dyes, where their applications are not only determined by their colour, but also their valuable chemical properties.

Merocyanine I

Names
Preferred IUPAC name Sodium 3-{(2Z)-2-[(2E)-4-(1,3-dibutyl-2,4,6-trioxo-1,3-diazinan-5-ylidene)but-2-en-1-ylidene]-1,3-benzoxazol-3(2H)-yl}propane-1-sulfonate
Identifiers
CAS Number	58823-12-4 Y
3D model (JSmol)	Interactive image
ChemSpider	4941661 N
PubChem CID	23678802
UNII	7V7WD5EDT7 Y
InChI InChI=1S/C26H33N3O7S.Na/c1-3-5-16-28-24(30)20(25(31)29(26(28)32)17-6-4-2)12-7-10-15-23-27(18-11-19-37(33,34)35)21-13-8-9-14-22(21)36-23;/h7-10,12-15H,3-6,11,16-19H2,1-2H3,(H,33,34,35);/q;+1/p-1/b10-7+,23-15-; N Key: DZVCFNFOPIZQKX-LTHRDKTGSA-M N
SMILES CCCCN1C(=O)C(=C/C=C/C=C\2/N(c3ccccc3O2)CCCS(=O)(=O)[O-])C(=O)N(C1=O)CCCC.[Na+]
Properties
Chemical formula	C26H32N3NaO7S
Molar mass	553.60 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

These dyes are usually intensely colored and have large extinction coefficients.

Merocyanine 540 was the first fluorescent dye used for measuring membrane potential, while Brooker's merocyanine and related compounds are notable for their solvatochromatic properties.

Merocyanine 540 differs from merocyanine I by the replacement of an oxygen atom with a sulfur atom

Definition

Conventionally, merocyanine class includes streptocyanines and their analogues where both the nitrogen atom and carbonyl group (or any other electron-withdrawing group containing a multiple carbon-heteroatomic bond, e.g. amino group) can form part of a heterocyclic system. Like ionic cyanines, merocyanines contain two terminal heteroatoms and a polymethine chain in their chromophores.

See also

• Brooker's merocyanine
• Cyanine
• J-aggregate