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A leuco dye (from the Greek leukos: white ) is a dye which can reversibly switch between two chemical forms; one of which is colorless. The transformation can be caused by heat, light or pH; resulting in examples of thermochromism, photochromism and halochromism respectively. The colorless form is sometimes referred to as the leuco form
The spiro form of an oxazine is a colorless leuco dye; the conjugated system of the oxazine and another aromatic part of the molecule is separated by an sp3-hybridized "spiro" carbon. After protonating a part of the molecule, irradiation with UV light (see Photochromism), or introducing other kind of such change, the bond between the spiro carbon and the oxazine interrupts, the ring opens, the spiro carbon achieves sp2 hybridization and becomes planar, the aromatic group rotates, aligns its π-orbitals with the rest of the molecule, and a conjugated system forms, with ability to absorb photons of visible light, and therefore appear colorful.
Another example of a leuco dye is the crystal violet lactone, which in its lactone form is colorless or slightly yellowish, but in low pH, when it is protonated, it becomes intensely violet. Other examples are phenolphthalein and thymolphthalein, colorless in acidic to neutral pH, but becoming pink and blue in alkaline environment. Other example are many redox indicators, which undergo reversible color change between colored and colorless form at a specific electrode potential.
- Flexplay, trademark for a DVD-compatible optical video disk format that uses leuco dye to intentionally "wear away" after a limited number of playings.
- Hypercolor, clothing that changes color with heat
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