Naphthalenetetracarboxylic diimide

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); bottom: model (grey: C, white: H, red: O, blue: N)
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 ;
3D model (JSmol)	Interactive image;
ChemSpider	72067;
EC Number	227-159-0;
PubChem CID	79771;
UNII	896Z6Y4WZP ;
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
	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)^{[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.

^ 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.
^ 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.
^ 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.
^ 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.

Names
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]
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