Naphthalocyanine

Naphthalocyanine is a cross-shaped organic molecule consisting of 48 carbon, 8 nitrogen and 26 hydrogen atoms, it is a derivative of phthalocyanine. IBM Research labs used it for developing single-molecule logic switches[1] and visualizing charge distribution in a single molecule.[2][3]

Naphthalocyanine
Schematic and AFM image
Names
IUPAC name
21H,23H-Tetranaphtho[2′,3′:2,3;2′′,3′′:7,8;2′′′,3′′′:12,13;2′′′ ′,3′′′ ′:17,18]porphyrin
Systematic IUPAC name
[11(2)Z,13(8)Z,33(4)Z,7(81)Z]-12H,52H-2,4,6,8-Tetraaza-1,3,5,7(1,3)-tetrakis(benzo[f]isoindola)cyclooctaphane-11(2),13(8),33(4),7(81)-tetraene
Other names
Tetrabenzo[g]quinoxalino-2,3-porphyrazine
Identifiers
3D model (JSmol)
ChemSpider
  • 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) checkY
    Key: LKKPNUDVOYAOBB-UHFFFAOYSA-N checkY
  • 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
Properties
C48H26N8
Molar mass 714.792 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Naphthalocyanine derivatives have a potential use in photodynamic cancer treatment.[4]

References
  1. Liljeroth, P.; Repp, J.; Meyer, G. (2007). "Current-Induced Hydrogen Tautomerization and Conductance Switching of Naphthalocyanine Molecules". Science. 317 (5842): 1203–1206. Bibcode:2007Sci...317.1203L. doi:10.1126/science.1144366. PMID 17761878.
  2. Mohn, F.; Gross, L.; Moll, N.; Meyer, G. (2012). "Imaging the charge distribution within a single molecule". Nature Nanotechnology. 7 (4): 227–231. Bibcode:2012NatNa...7..227M. doi:10.1038/NNANO.2012.20. PMID 22367099.
  3. "Scientists image the charge distribution within a single molecule for the first time". Physorg.com. 2012-02-27. Retrieved 2012-02-27.
  4. 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): 276–85. doi:10.1117/1.429930. PMID 23015248.


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