Naphthalenetetracarboxylic diimide

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.

Naphthalenetetracarboxylic diimide

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
CAS Number	5690-24-4 Y
3D model (JSmol)	Interactive image
ChemSpider	72067
EC Number	227-159-0
PubChem CID	79771
UNII	896Z6Y4WZP Y
CompTox Dashboard (EPA)	DTXSID30205440
InChI 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
SMILES c1cc2c3c(ccc4c3c1C(=O)NC4=O)C(=O)NC2=O
Properties
Chemical formula	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). Infobox references

Properties

Synthesis of symmetric and unsymmetric NDIs.

NTCDI is redox-active, forming stable radical anions near -1.10 V vs. Fc/Fc⁺.^[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]

References

1. Hapala, Prokop; Kichin, Georgy; Wagner, Christian; Tautz, F. Stefan; Temirov, Ruslan; Jelínek, Pavel (2014-08-19). "Mechanism of high-resolution STM/AFM imaging with functionalized tips". Physical Review B. 90 (8): 085421. arXiv:1406.3562. Bibcode:2014PhRvB..90h5421H. doi:10.1103/PhysRevB.90.085421. S2CID 53610973.
2. Hämäläinen, Sampsa K.; van der Heijden, Nadine; van der Lit, Joost; den Hartog, Stephan; Liljeroth, Peter; Swart, Ingmar (2014-10-31). "Intermolecular Contrast in Atomic Force Microscopy Images without Intermolecular Bonds". Physical Review Letters. 113 (18): 186102. arXiv:1410.1933. Bibcode:2014PhRvL.113r6102H. doi:10.1103/PhysRevLett.113.186102. PMID 25396382. S2CID 8309018.
3. 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: 3931. Bibcode:2014NatCo...5.3931S. doi:10.1038/ncomms4931. PMC 4050271. PMID 24875276.
4. 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.
5. Bhosale, Sheshanath V.; Jani, Chintan H.; Langford, Steven J. (2008). "Chemistry of naphthalene diimides". Chem. Soc. Rev. 37 (2): 331–342. doi:10.1039/b615857a. PMID 18197349.
6. 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): 268–284. doi:10.1002/adma.201001402. PMID 21154741. S2CID 15222824.