Naphthalenetetracarboxylic diimide

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Naphthalenetetracarboxylic diimide
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
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) 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.

NTCDI is redox-active, forming stable

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]

References

  1. S2CID 53610973
    .
  2. S2CID 8309018
    .
  3. PMID 24875276
    .
  4. ISBN 978-0-8493-0445-3
    .
  5. PMID 18197349
    .
  6. S2CID 15222824
    .
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