Cas no 132196-66-8 (Perylene, 3-ethynyl-)

Perylene, 3-ethynyl-, is a functionalized perylene derivative characterized by the presence of an ethynyl group at the 3-position of the perylene core. This modification enhances its utility in organic electronic applications, such as organic semiconductors, light-emitting diodes (OLEDs), and photovoltaic devices, due to improved conjugation and electron transport properties. The ethynyl group also facilitates further chemical derivatization, enabling tailored material design for specific optoelectronic requirements. Its high thermal stability and strong fluorescence make it suitable for advanced materials research. The compound is typically handled under inert conditions to preserve its reactive alkyne functionality.
Perylene, 3-ethynyl- structure
Perylene, 3-ethynyl- structure
Product Name:Perylene, 3-ethynyl-
CAS No:132196-66-8
MF:C22H12
MW:276.33068561554
CID:165858
PubChem ID:125532
Update Time:2025-09-22

Perylene, 3-ethynyl- Chemical and Physical Properties

Names and Identifiers

    • Perylene, 3-ethynyl-
    • 3-ethynylperylene
    • 3-Ethynyl perylene
    • R02-0002
    • DTXSID60157423
    • 132196-66-8
    • BP-28910
    • VOVKFLKDPQAQIR-UHFFFAOYSA-N
    • 3-perylenylacetylene
    • DTXCID6079914
    • Inchi: 1S/C22H12/c1-2-14-12-13-20-18-10-4-7-15-6-3-9-17(21(15)18)19-11-5-8-16(14)22(19)20/h1,3-13H
    • InChI Key: VOVKFLKDPQAQIR-UHFFFAOYSA-N
    • SMILES: C12C3=CC=CC=1C1=CC=CC4=CC=CC(C2=CC=C3C#C)=C14

Computed Properties

  • Exact Mass: 276.09396
  • Monoisotopic Mass: 276.093900383g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 1
  • Complexity: 482
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 6
  • Topological Polar Surface Area: 0?2

Experimental Properties

  • PSA: 0

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Additional information on Perylene, 3-ethynyl-

Perylene, 3-ethynyl- (CAS No. 132196-66-8): A Versatile Compound in Modern Chemical Research

Perylene, 3-ethynyl-, with the chemical formula C20H12N and CAS number 132196-66-8, is a highly intriguing molecule that has garnered significant attention in the field of chemical biology and materials science. This compound, a derivative of perylene, a polycyclic aromatic hydrocarbon (PAH), exhibits unique structural and electronic properties that make it invaluable for various applications, including optoelectronic devices, photodynamic therapy, and as a building block for more complex molecular architectures.

The structure of Perylene, 3-ethynyl features a perylene core substituted with an ethynyl group at the 3-position. This ethynyl functionality introduces a site for further chemical modification, enabling the synthesis of a wide range of derivatives with tailored properties. The perylene core itself is known for its high thermal stability, excellent light absorption characteristics, and ability to form stable π-stacking interactions, making it an ideal candidate for applications in organic electronics.

In recent years, the chemical biology applications of Perylene, 3-ethynyl have been extensively explored. One of the most notable areas is its use as a photosensitizer in photodynamic therapy (PDT). PDT is a medical treatment that uses light-sensitive dyes to produce reactive oxygen species upon irradiation with light, leading to the destruction of cancer cells. The high molar extinction coefficient and strong absorption in the near-infrared region of the spectrum make Perylene, 3-ethynyl an excellent candidate for this purpose. Recent studies have demonstrated its efficacy in targeting and destroying tumor cells while minimizing damage to surrounding healthy tissue.

Furthermore, the optoelectronic properties of Perylene, 3-ethynyl have been leveraged in the development of organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). The compound's ability to form stable π-stacking interactions allows for efficient charge transport, which is crucial for the performance of these devices. In OLEDs, Perylene, 3-ethynyl has been used as a host material or dopant to improve electroluminescence efficiency. Similarly, in OPVs, it has been employed as a donor material due to its favorable energy levels and hole-transporting capabilities.

The synthesis of Perylene, 3-ethynyl can be achieved through various methods, including palladium-catalyzed cross-coupling reactions such as Sonogashira coupling. This reaction involves the coupling of an acetylide with an aryl halide or triflate under palladium catalysis to form an alkyne. The Sonogashira coupling reaction is particularly useful for introducing the ethynyl group into the perylene core. Other synthetic approaches include electrochemical methods and photocatalytic processes, which offer advantages in terms of selectivity and mild reaction conditions.

Recent advancements in material science have highlighted the potential of Perylene, 3-ethynyl as a component in advanced materials. For instance, it has been incorporated into polymers and nanoparticles to enhance their optical and electronic properties. These materials have found applications in sensors, catalysts, and even in the development of novel drug delivery systems. The ability to tune the properties of these materials by modifying the structure of Perylene, 3-ethynyl makes it a highly versatile building block.

The biological activity of Perylene, 3-ethynyl has also been studied extensively. While perylenes are known for their potential toxicity due to their PAH structure, modifications such as the introduction of an ethynyl group can alter their biological profile. Research has shown that certain derivatives can exhibit anti-inflammatory and anti-proliferative effects. These findings have opened up new avenues for exploring Perylene, 3-ethynyl as a lead compound for drug discovery.

In conclusion, Perylene, 3-ethynyl (CAS No. 132196-66-8) is a multifaceted compound with significant potential in various fields of research. Its unique structural and electronic properties make it an invaluable tool for developing new materials and therapies. As research continues to uncover more about its capabilities, Perylene, 3-ethynyl is likely to play an increasingly important role in advancing both chemical biology and materials science.

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