Naphthalenetetracarboxylic diimide

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Naphthalenetetracarboxylic diimide
NTCDI AFM2a.jpg
Top: AFM image of NTCDI molecules on silver interacting via hydrogen bonding (the hydrogen bonds are exaggerated by artifacts of the imaging technique [1] [2] ); bottom: model (grey: C, white: H, red: O, blue: N) [3]
Names
Preferred IUPAC name
Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone
Other names
1,4,5,8-Naphthalenetetracarbondiimide
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 227-159-0
PubChem CID
UNII
  • InChI==1S/C14H6N2O4/c17-11-5-1-2-6-10-8(14(20)16-12(6)18)4-3-7(9(5)10)13(19)15-11/h1-4H,(H,15,17,19)(H,16,18,20)
    Key: BODUWJSFPLUDMP-UHFFFAOYSA-N
  • c1cc2c3c(ccc4c3c1C(=O)NC4=O)C(=O)NC2=O
Properties
C14H6N2O4
Molar mass 266.212 g·mol−1
Melting point > 300 °C [4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Naphthalenetetracarboxylic diimide (NTCDI)[ pronunciation? ] is a solid organic compound and one of the simplest naphthalenediimides (NDIs). NTCDI is produced from the parent naphthalene via an intermediate compound naphthalenetetracarboxylic dianhydride.

Properties

Synthesis of symmetric and unsymmetric NDIs. NDIpreps.png
Synthesis of symmetric and unsymmetric NDIs.

NTCDI is redox-active, forming stable radical anions at –1.10 V vs. Fc/Fc+ in Dichloromethane. [5] Its ability to accept electrons reflects the presence of an extended conjugated ring system and the electron withdrawing groups (carbonyl centers). NDI is used in supramolecular chemistry owing to its tendency to form charge-transfer complexes with crown ethers, e.g., to give rotaxanes and catenanes. As another consequence of their planar structure and electron-acceptor properties, NDIs intercalate into DNA. It is also suitable for fabrication of soft electronic devices. [6]

Related Research Articles

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References

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