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Tetrazine-Bridged Phthalocyaninato Metal Complexes: A New Class Of Intrinsic Semiconductors

Published online by Cambridge University Press:  16 February 2011

Michael Hanack ,
Jose Osio Barcina ,
JöRg Pohmer  and
Elisabeth Witke
Michael Hanack
Affiliation:
Institut für Organische Chemie, Lehrstuhl für Organische Chemie II der Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany
Jose Osio Barcina
Affiliation:
Institut für Organische Chemie, Lehrstuhl für Organische Chemie II der Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany
JöRg Pohmer
Affiliation:
Institut für Organische Chemie, Lehrstuhl für Organische Chemie II der Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany
Elisabeth Witke
Affiliation:
Institut für Organische Chemie, Lehrstuhl für Organische Chemie II der Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany
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Abstract

Stacked transition Metal Macrocycles [Macm (L)]n with M e.g. Fe, Ru, Os, Co, Rh and Mac = phthalocyanine (Pc) 1,2- or 2,3-naphthalocyanine (1,2-, 2,3-Nc) have been synthesized by us. The bridging ligands (L) are e.g. pyrazine (pyz) or s-tetrazine (tz). In general, these complexes [Macm (L)]n are insoluble in organic solvents, however, soluble oligomers [R4Pcm (L)]n can be prepared using Metallomacrocycles RnPcm, R = t-bu, et, OR, M = Fe, Ru, which are substituted in the périphérie positions.

A systematic investigation of the influence of the bridging ligánds on the semiconducting properties in [Macm (L)]n reveal, that changing L, e.g from dabco over pyz to tz leads to a steady increase of the semiconducting properties without external oxidative doping. Powder conductivities in the order of 0.1 S/cm can be reached by using s-tetrazine, 3,6-dimethyl-j-tetrazine (Me2tz) and others, e.g. fu marodini tri le as the bridging ligands. The intrinsic conductivities are a result of the low oxidation potential of tz and Me2tz and due to the low lying LUMO in the corresponding bridged systems [Macm (tz)]n.

The electrical and physical properties, especially the UV and the Möβbauer spectra for the tetrazine-bridged Macrocyclic Metal complexes are discussed in respect to intrinsic semiconducting properties of these compounds.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 328: Symposium Q – Electrical, Optical, and Magnetic Properties of Organic Solid State Materials , 1993 , 233
Copyright
Copyright © Materials Research Society 1994

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References

REFERENCES

[1] (a) Hanack, M., Datz, A., Fay, R., Fischer, K., Keppeler, U., Koch, J., Metz, J., Mezger, M., Schneider, O. and Schulze, H.-J., Handbook of Conducting Polymers; Skotheim, T.A., Ed., Marcel Dekker, New York, 1986;Google Scholar
(b) Hanack, M., Deger, S. and Lange, A., Coord. Chem. Reviews 83, 115 (1988);CrossRefGoogle Scholar
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[2] Hanack, M., Keppeler, U., Lange, A., Hirsch, A. and Dieing, R. in: “Phthalocyanines, Properties and Applications”, VCH Publishers, Weinheim 1993, Vol. 2, p. 43.Google Scholar