Dichlorphenolindophenol

Chembox new
Name = DCPIP
ImageFile1 = DCPIP-2D-skeletal.png ImageSize1 = 150px
ImageFileL2 = Dichlorphenolindophenol-3D-balls.png ImageSizeL2 = 100px
ImageFileR2 = Dichlorphenolindophenol-3D-vdW.png ImageSizeR2 = 100px
IUPACName = 2,6-dichlorophenol-indophenol
OtherNames = 2,5-cyclohexadien-1-one;
dichloroindophenol;
2,6-dichloro-4- [(4-hydroxyphenyl)imino] -2,6-dichloroindophenol;
2,6-Dichloro-4-((4-hydroxyphenyl)imino) -2,5-cyclohexadien-1-one
Section1 = Chembox Identifiers
CASNo = 956-48-9
SMILES = O=C(C(Cl)=C2)C(Cl)=C/ C2=NC1=CC=C(O)C=C1
Section2 = Chembox Properties
Formula = C₁₂H₇NCl₂O₂
MolarMass = 268.1 g mol⁻¹
Density =
MeltingPt =
BoilingPt =

2,6-dichlorophenolindophenol, ( DCPIP ) is a blue chemical compound used as a redox dye. Oxidized DCPIP is blue, reduced DCPIP is colorless.

The rate of photosynthesis can be measured by the rate at which this dye is broken down (reduced) when exposed to light in a photosynthetic system. This reaction is reversible, as colorless DCPIP can be reoxidized to blue. It is often used in measurements of the electron transport chain in plants because of its higher [affinity] for electrons than ferredoxin. For example, it is possible to compare rates of photosynthesis with DCPIP. Due to the reductions that occur during the light reactions, DCPIP can be substituted for NADPH, the final electron carrier in the light reactions. The light reactions will reduce the DPIP and turn it colorless. As DCPIP is reduced and becomes colorless, the following increase in light transmittance can be measured by a spectrophotometer.

DCPIP

DCPIP is a redox dye commonly used as a monitor of the light reactions in photosynthesis because it is an electron acceptor that is blue when oxidized and colorless when reduced. It is part of the Hill reagents family. DPIP is commonly used as a substitute for NADP⁺. The dye changes color when it is reduced, due to its chemical structure. The nitrogen atom in the center of the molecule is the atom that accepts electrons, and it changes the double N-C bond to a single bond, which forces bonds between carbons in the entire left ring to change. This microscopic shift in the DCPIP structure causes the macroscopic change in color, from dark blue to colorless.

The rate of photosynthesis light-dependent reaction can be measured with this property of DCPIP, because one of the stages of the light reaction is an electron transport chain that normally ends with the reduction of NADP⁺. When DCPIP is present, it also gets reduced by the light reaction. The amount of DCPIP reduced can be found by measuring the solution's light transmittance with a spectrophotometer.

Using DCPIP to determine the concentration of ascorbic acid or Vitamin C in a solution.

DCPIP is commonly used as an indicator for Vitamin C. If vitamin C, which is a good reducing agent is present , the blue dye, which turns pink in acid conditions and is reduced to a colorless compound by ascorbic acid.

:DCPIP (blue) + H⁺ ----------> DCPIPH (pink):DCPIPH (pink) + VitC ----------> DCPIPH2 (colorless):C₆H₈O₆ + C₁₂H₇NCl₂O₂ ----------> C₆H₆O₆ + C₁₂H₉NCl₂O₂

In a titration, when all the ascorbic acid in the solution has been used up, there will not be any electrons available to reduce the DCPIPH and the solution will remain pink due to the DCPIPH. The end point is a pink color that persists for 10 seconds or more.

ee also

*Indophenol
*Metachromasy

References

* Derek Denby, "Chemistry Review", May 1996