2,3,5,6-Tetrafluoro-7,7',8,8'-tetracyanoquinodimethane - ≥97% , CAS No.29261-33-4

CAS: 29261-33-4 Cat. No.: T101365 Molecular Weight: 276.15 Beilstein Registry Number: 2157887 EC Number: 624-300-1 PubChem CID: 2733307

GRADE & PURITY ≥97%

Synonyms

MFCD00042382 | BCP18920 | 2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-quinodimethane | YSWG343 | (2,3,5,6-Tetrafluoro-2,5-cyclohexadiene-1,4-diylidene)dimalononitrile | F4TCNQ | 2-[4-(dicyanomethylene)-2,3,5,6-tetrafluoro-cyclohexa-2,5-dien-1-ylidene]propanedi

Storage

Room temperature

Shipped In

Normal

Overview

2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) is a dopant used in the fabrication of organic semiconductors. It can tune the electronic properties as its lowest unoccupied molecular orbital is at a desirable energy level required to oxidize a wide range of semiconductors.
2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) are p-type molecules, used as a strong acceptor dopant , it generates free holes.

Application：

F4-TCNQ can be doped with poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTAA) to form a hole transport material (HTL), which can be used to achieve an energy efficiency of 16% for a semi-transparent perovskite solar cell.It can be used as a p-type dopant to form a blended composite film with poly(3-hexylthiophene) (P3HT) having enhanced charge mobility, which can be potentially useful in organic photovoltaics.
F4-TCNQ is the p-type dopant for hole-only devices and field effect transistors with organic hole transport layers (HTL).It is used in the preparation of a bilayer structure of F4-TCNQ and pentacene to study improved thermoelectric performance of organic thin films.

Specifications

Synonyms

MFCD00042382 | BCP18920 | 2, 3, 5, 6-tetrafluoro-7, 7, 8, 8-tetracyano-quinodimethane | YSWG343 | (2, 3, 5, 6-Tetrafluoro-2, 5-cyclohexadiene-1, 4-diylidene)dimalononitrile | F4TCNQ | 2-[4-(dicyanomethylene)-2, 3, 5, 6-tetrafluoro-cyclohexa-2, 5-dien-1-ylidene]propanedi

Specifications & Purity

≥97%

Storage

Room temperature

Shipped In

Normal

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 488192385
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488192385
• Canonical Smiles: C(#N)C(=C1C(=C(C(=C(C#N)C#N)C(=C1F)F)F)F)C#N
• IUPAC Name: 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile
• InChIKey: IXHWGNYCZPISET-UHFFFAOYSA-N
• INCHI: 1S/C12F4N4/c13-9-7(5(1-17)2-18)10(14)12(16)8(11(9)15)6(3-19)4-20
• Isomeric SMILES: C(#N)C(=C1C(=C(C(=C(C#N)C#N)C(=C1F)F)F)F)C#N
• WGK Germany: 3
• PubChem CID: 2733307
• Molecular Weight: 276.15
• Beilstein: 2157887
• Reaxy-Rn: 2157887

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Hydrocarbon derivatives
    • Class Quinodimethanes
      • Subclass P-quinodimethanes

• Kingdom: Organic compounds
• Superclass: Hydrocarbon derivatives
• Class: Quinodimethanes
• Subclass: P-quinodimethanes
• Intermediate Tree Nodes: Not available
• Direct Parent: P-quinodimethanes
• Alternative Parents: Fluorobenzenes Aryl fluorides Nitriles Organopnictogen compounds Organofluorides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: P-quinodimethane - Halobenzene - Fluorobenzene - Benzenoid - Monocyclic benzene moiety - Aryl halide - Aryl fluoride - Nitrile - Carbonitrile - Organic nitrogen compound - Organopnictogen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as p-quinodimethanes. These are compounds containing a benzene ring conjugated to two methylidene groups at carbon atoms 1 and 4, respectively..
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Melt Point(°C): 291°C
• Molecular Weight: 276.150 g/mol
• XLogP3: 0.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 0
• Exact Mass: 276.006 Da
• Monoisotopic Mass: 276.006 Da
• Topological Polar Surface Area: 95.200 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 697.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Junsheng Luo, Chunyang Jia, Zhongquan Wan, Fei Han, Bowen Zhao, Ruilin Wang.  (2017)  The novel dopant for hole-transporting material opens a new processing route to efficiently reduce hysteresis and improve stability of planar perovskite solar cells.  JOURNAL OF POWER SOURCES,      [PMID:] [10.1016/j.jpowsour.2017.01.010]

2. Zuwang Liu, Zhan Su, Bo Yu, Yapeng Sun, Jiankai Zhang, Huangzhong Yu.  (2024)  Biomaterial Improves the Stability of Perovskite Solar Cells by Passivating Defects and Inhibiting Ion Migration.  ACS Applied Materials & Interfaces,      [PMID:38842482] [10.1021/acsami.4c06285]

3. Yuanyuan Wang, Dawei Yang, Heng Zhang.  (2024)  PEDOT:PSS-Free Quantum-Dot Light-Emitting Diode with Enhanced Efficiency and Stability.  ACS Applied Materials & Interfaces,      [PMID:39420653] [10.1021/acsami.4c13899]

4. Xiaona Li, Hang Luo, Yuting Wan, Bo Peng, Yuan Liu, Sheng Chen, Dou Zhang.  (2024)  Ultra-high electron affinity and peripheral electronegativity co-constructing all-organic dielectrics with outstanding capacitive performance at high temperature.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.150874]

5. Jihong Wang, Wenhao Liu, Qiubo Pan, Lei Zhang, Junchao Ren, Haiping Fang.  (2024)  Simple ultrasonic mixing to obtain charge transfer dopants of graphene oxide for highly responsive photodetectors and efficient image extraction.  CARBON,      [PMID:] [10.1016/j.carbon.2024.119529]