Diketopyrrolopyrroles (DPPs) are organic

dye Juan de Guillebon, better known by his stage name DyE, is a French musician. He is known for the music video of the single "Fantasy Fantasy is a genre of speculative fiction that involves supernatural or Magic (supernatural), magical ele ...

s and

pigments A pigment is a powder used to add or alter color or change visual appearance. Pigments are completely or nearly solubility, insoluble and reactivity (chemistry), chemically unreactive in water or another medium; in contrast, dyes are colored sub ...

based on the heterocyclic dilactam 2,5-dihydropyrrolo ,4-''c''yrrole-1,4-dione, widely used in

optoelectronics Optoelectronics (or optronics) is the study and application of electronic devices and systems that find, detect and control light, usually considered a sub-field of photonics. In this context, ''light'' often includes invisible forms of radi ...

. DPPs were initially used as pigments in the painting industry (e.g. in

automotive paint Automotive paint is paint used on automobiles for both protective and decorative purposes. Water-based Acrylate polymer, acrylic polyurethane enamel paint is currently the most widely used paint for reasons including reducing paint's Environmenta ...

s) due to their high resistance to

photodegradation Photodegradation is the alteration of materials by light. Commonly, the term is used loosely to refer to the combined action of sunlight and air, which cause oxidation and hydrolysis. Often photodegradation is intentionally avoided, since it dest ...

. More recently, DPP derivatives have been also investigated as promising

fluorescent dyes A fluorophore (or fluorochrome, similarly to a chromophore) is a fluorescent chemical compound that can re-emit light upon light excitation. Fluorophores typically contain several combined aromatic groups, or planar or cyclic molecules with sev ...

for bioimaging applications, as well as components of materials for use in

organic electronics Organic electronics is a field of materials science concerning the design, Chemical synthesis, synthesis, characterization, and application of Organic compound, organic molecules or polymers that show desirable Electronics, electronic properties ...

Structure

DPP dyes are based on the bicyclic heterocyclic compound diketopyrrolopyrrole. 2,5-Dihydropyrrolo ,4-cyrrole-1,4-dione is a basic body of Diketopyrrolopyrrole dye. DPP pigments are an important class of high-performance pigments used in inks, paints and plastic. More recently their optical-electronic performance was discovered for

photovoltaic Photovoltaics (PV) is the conversion of light into electricity using semiconducting materials that exhibit the photovoltaic effect, a phenomenon studied in physics, photochemistry, and electrochemistry. The photovoltaic effect is commercially ...

applications and related uses.

Optical properties

DPP has high stability to heat but not very well to

acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...

and base. The

alkylation Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

of amide groups improves the solubility. The modified DDP shows high

fluorescence Fluorescence is one of two kinds of photoluminescence, the emission of light by a substance that has absorbed light or other electromagnetic radiation. When exposed to ultraviolet radiation, many substances will glow (fluoresce) with colore ...

and the emission

wavelength In physics and mathematics, wavelength or spatial period of a wave or periodic function is the distance over which the wave's shape repeats. In other words, it is the distance between consecutive corresponding points of the same ''phase (waves ...

is adjustable by change the aromatic group at 3 and 6 positions. Both

electron donor In chemistry, an electron donor is a chemical entity that transfers electrons to another compound. It is a reducing agent that, by virtue of its donating electrons, is itself oxidized in the process. An obsolete definition equated an electron dono ...

group, such as

thiophene Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reacti ...

, and expanding of the

conjugated system In physical organic chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases Chemical stability, stability. It is Reson ...

increase the emission wavelength. DPP is also developed as a red emitting group in pure polymer light emitting diodes. Some DPP derivatives show aggregation induced emission and were used as effective fluorescent

sensor A sensor is often defined as a device that receives and responds to a signal or stimulus. The stimulus is the quantity, property, or condition that is sensed and converted into electrical signal. In the broadest definition, a sensor is a devi ...

s, in organic solar cells.

References

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Structure

Optical properties

References

Further reading