Lutetium phthalocyanine

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Lutetium phthalocyanine
Names
Other names
Lutetium bisphthalocyanine
Lutetium biphthalocyanine
Identifiers
3D model (
JSmol
)
  • InChI=1S/2C32H16N8.Lu/c2*1-2-10-18-17(9-1)25-33-26(18)38-28-21-13-5-6-14-22(21)30(35-28)40-32-24-16-8-7-15-23(24)31(36-32)39-29-20-12-4-3-11-19(20)27(34-29)37-25;/h2*1-16H;/q2*-2;+3 StdInChIKey=YBUYPYVECVICRC-UHFFFAOYSA-N
  • C15=CC=CC=C1C6=NC9=C2C=CC=CC2=C(N=C4C3=CC=CC=C3C(=N4)N=C7C8=C(C(=NC5=N6)[N-]7)C=CC=C8)[N-]9.C%10%14=CC=CC=C%10C%15=NC%18=C%11C=CC=CC%11=C(N=C%13C%12=CC=CC=C%12C(=N%13)N=C%16C%17=C(C(=NC%14=N%15)[N-]%16)C=CC=C%17)[N-]%18.[Lu+3]
Properties
LuC64H32N16
Molar mass 1200.04 g/mol
Appearance green solid; red when oxidized; blue when reduced
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lutetium phthalocyanine (LuPc2) is a

coordination compound derived from lutetium and two phthalocyanines. It was the first known example of a molecule that is an intrinsic semiconductor.[1][2] It exhibits electrochromism
, changing color when subject to a voltage.

Structure

LuPc2 is a double-decker

free radical[1] with the unpaired electron sitting in a half-filled molecular orbital between the highest occupied and lowest unoccupied orbitals, allowing its electronic properties to be finely tuned.[3]

Properties

LuPc2, along with many substituted derivatives like the alkoxy-methyl derivative Lu[(C8H17OCH2)8Pc]2, can be deposited as a thin film with intrinsic semiconductor properties;[4] said properties arise due to its radical nature[1] and its low reduction potential compared to other metal phthalocyanines.[2] This initially green film exhibits electrochromism; the oxidized form LuPc+
2 is red, whereas the reduced form LuPc−
2 is blue and the next two reduced forms are dark blue and violet, respectively.[4] The green/red oxidation cycle can be repeated over 10,000 times in aqueous solution with dissolved alkali metal halides, before it is degraded by hydroxide ions; the green/blue redox degrades faster in water.[4]

Electrical properties

LuPc2 and other lanthanide phthalocyanines are of interest in the development of organic thin-film field-effect transistors.[3][5]

LuPc2 derivatives can be selected to change color in the presence of certain molecules, such as in

NADH.[6]


References

  1. ^
    doi:10.1021/j100361a026
    .
  2. ^
    doi:10.1016/0925-4005(92)80169-X
    .
  3. ^
    PMID 23802970
    .
  4. ^
    doi:10.1039/A905248H
    .
  5. doi:10.1063/1.1840093
    .
  6. doi:10.1016/j.optmat.2012.10.017
    .
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