Napthalenetetracarboxylic diimide

Napthalenetetracarboxylic diimide

Top: AFM image of NTCDI molecules on silver interacting via hydrogen bonding; bottom: model (grey: C, white: H, red: O, blue: N)[1]
Names
Systematic IUPAC name Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone
Other names 1,4,5,8-Naphthalenetetracarbondiimide
Identifiers
CAS Number	5690-24-4
ChemSpider	72067
EC Number	227-159-0
Jmol interactive 3D	Image
InChI Key: BODUWJSFPLUDMP-UHFFFAOYSA-N 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)
SMILES c1cc2c3c(ccc4c3c1C(=O)NC4=O)C(=O)NC2=O
Properties
Chemical formula	C14H6N2O4
Molar mass	266.21 g·mol^−1
Melting point	> 300 °C[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 radical anions near -1.10 V vs. Fc/Fc⁺.^[3] 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.^[4]

References

1. Sweetman, A. M.; Jarvis, S. P.; Sang, Hongqian; Lekkas, I.; Rahe, P.; Wang, Yu; Wang, Jianbo; Champness, N.R.; Kantorovich, L.; Moriarty, P. (2014). "Mapping the force field of a hydrogen-bonded assembly". Nature Communications 5. doi:10.1038/ncomms4931.
2. Lide, David R.; Milne, G.W.A. (1993). CRC Handbook of Data on Organic Compounds. CRC Press. p. 1522. ISBN 978-0-8493-0445-3.
3. Bhosale, Sheshanath V.; Jani, Chintan H.; Langford, Steven J. (2008). "Chemistry of naphthalene diimides". Chem. Soc. Rev 37 (2): 331. doi:10.1039/b615857a. PMID 18197349.
4. Zhan, Xiaowei; Facchetti, Antonio; Barlow, Stephen; Marks, Tobin J.; Ratner, Mark A.; Wasielewski, Michael R.; Marder, Seth R. (2011). "Rylene and Related Diimides for Organic Electronics". Advanced Materials 23 (2): 268. doi:10.1002/adma.201001402. PMID 21154741.