Naphthalocyanine

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Naphthalocyanine

IUPAC name (2Z,15Z,27Z,41Z)-2,15,28,41,53,54,55,56-octaazatridecacyclo[40.10.1.1^3,14.1^16,27.1^29,40.0^4,13.0^6,11.0^17,26.0^19,24.0^30,39.0^32,37.0^43,52.0^45,50]hexapentaconta-1(53),2,4,6,8,10,12,14(56),15,17,19,21,23,25,27,29,31,33,35,37,39,41,43,45,47,49,51-heptacosaene (non-preferred name)
Other names Tetrabenzo[g]quinoxalino-2,3-porphyrazine
Identifiers
CAS number	23627-89-6^Y
PubChem	5748311
ChemSpider	4677874^Y
Jmol-3D images	Image 1
SMILES C1(/N=C(C2=C/3C=C4C=CC=CC4=C2)\NC3=N/C(C5=C/6C=C(C=CC=C7)C7=C5)=NC6=N/8)=N/C(C9=CC%10=CC=CC=C%10C=C19)=N\C%11=C%12C=C%13C=CC=CC%13=CC%12=C8N%11
InChI InChI=1S/C48H26N8/c1-2-10-26-18-34-33(17-25(26)9-1)41-49-42(34)54-44-37-21-29-13-5-6-14-30(29)22-38(37)46(51-44)56-48-40-24-32-16-8-7-15-31(32)23-39(40)47(52-48)55-45-36-20-28-12-4-3-11-27(28)19-35(36)43(50-45)53-41/h1-24H,(H2,49,50,51,52,53,54,55,56)^Y Key: LKKPNUDVOYAOBB-UHFFFAOYSA-N^Y
Properties
Molecular formula	C₄₈H₂₆N₈
Molar mass	714.77 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Naphthalocyanine is a derivative of phthalocyanine used as a component in the development of IBM's single-molecule logic switch.^[1]

It was used to show the first images of charge distribution over a single molecule in November 2011.^[2]^[3]

Its derivatives may also have uses in photodynamic cancer treatment.^[4]

References

↑ Liljeroth, P.; Repp, J.; Meyer, G. (2007). "Current-Induced Hydrogen Tautomerization and Conductance Switching of Naphthalocyanine Molecules". Science 317 (5842): 1203–1206. doi:10.1126/science.1144366. PMID 17761878.
↑ Mohn, F.; Gross, L.; Moll, N.; Meyer, G. (2012). "Imaging the charge distribution within a single molecule". Nature Nanotechnology. doi:10.1038/NNANO.2012.20.
↑ "Scientists image the charge distribution within a single molecule for the first time". Physorg.com. 2012-02-27. Retrieved 2012-02-27.
↑ Shopova, M.; Woehrle, D.; Mantareva, V.; Mueller, S. (1999). "Naphthalocyanine Complexes as Potential Photosensitizers for Photodynamic Therapy of Tumors". Journal of Biomedical Optics 4 (3): 276. doi:10.1117/1.429930.

Timmer, J. (2007) Storing data in molecules: shifting atoms and flipping bits, ars technica online [accessed 8 September 2007]

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