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CAS 74-31-7

N,N'-Diphenyl-1,4-phenylenediamine TCI D0609

N,N'-Diphenyl-1,4-phenylenediamine TCI D0609

Chemical Identity

Other names
DPPD
CAS No.
74-31-7
PubChem
CID 6319·SID 87567258
Formula
C18H16N2
Molecular weight
260.34 g/mol
Purity
>95.0%(T)
Reference databases
ChEBI·ChemSpider·ECHA
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
1-N,4-N-diphenylbenzene-1,4-diamine
SMILES
C1=CC=C(C=C1)NC2=CC=C(C=C2)NC3=CC=CC=C3
InChIKey
UTGQNNCQYDRXCH-UHFFFAOYSA-N
MDL
MDL00003015
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N,N'-Diphenyl-1,4-phenylenediamine, often abbreviated as DPPD, is an aromatic diamine. Its central phenylene ring carries two NH-phenyl groups in the para positions. In materials science it is classed as a small molecule semiconductor building block, because its triarylamine-type framework is electron-rich and can be oxidised reversibly. In the laboratory, DPPD serves as a building unit for hole transport materials, as a model compound for redox systems, and as an antioxidant in polymer and rubber research.

DPPD is chosen mainly for its redox behaviour. Both nitrogen atoms can give up electrons one step at a time, forming radical cation and quinonediimine species. This makes the compound a useful structural model that resembles the repeating unit of polyaniline. Its electron-donating character matters when designing organic electronic materials, and its ability to trap radicals explains why it works as an antioxidant. The NH groups can also be functionalised further, for example through coupling reactions, to build larger semiconducting molecules from this compact core.

In Indonesia, DPPD is relevant to laboratories working in materials science, polymer chemistry, electrochemistry and physical chemistry. University research groups use it to synthesise and study hole transport materials for organic electronic devices. Electrochemistry laboratories use it as a well-defined redox model, and polymer and rubber research teams use it to study antioxidant mechanisms. Because it is supplied under the TCI brand, researchers can use it as a dependable starting point for routine experiments and for new materials development.

TCI brochures (PDF)

  • Hole transport material synthesis: the electron-rich triarylamine-type framework and reversible oxidation make DPPD a suitable core unit for building organic hole transport compounds.
  • Redox model studies: stepwise electron loss from both nitrogen atoms to form radical cation and quinonediimine species makes DPPD a clear model system for studying multi-step redox behaviour.
  • Polyaniline structural modelling: DPPD resembles the repeating unit of polyaniline, so researchers can study the redox states of the polymer using a small, well-defined molecule.
  • Antioxidant research in polymers and rubber: DPPD's ability to trap radicals makes it a useful reference compound for studying how oxidative degradation is slowed in polymer and rubber formulations.
  • Building larger semiconducting molecules: the reactive NH groups can be functionalised further, for example through coupling reactions, to assemble extended small molecule semiconductors for organic electronics research.

Brand TCI (product code D0609)
CAS number 74-31-7
Molecular formula —
Purity —
Category Materials Science > Material Building Blocks > Small Molecule Semiconductor Building Blocks
Pack sizes as listed in the options on this product page
Physical form see the TCI certificate of analysis and safety data sheet supplied with the product
Storage keep tightly closed in a cool, dry place away from light and oxidising agents

DPPD oxidises easily, so store it in its original, tightly closed container in a cool, dry, well-ventilated place away from direct light, heat and oxidising agents. Close the container promptly after each use to limit contact with air and moisture. Handle the material in a fume hood or another well-ventilated area, and wear standard personal protective equipment: laboratory gloves, safety glasses and a lab coat. Avoid creating dust, and do not inhale it or let it touch the skin or eyes. Read the safety data sheet supplied with the product before use, and dispose of residues and contaminated materials according to local chemical waste regulations.

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