ZB-6 Chemistry of Porphyrins and Metalloporphyrin

Prof. Lechosław Latos-Grażyński

Corresponding Member of the Polish Academy of Sciences


M.Sc. 1974, Ph.D. 1978, D.Sc. 1986, Prof. 1992


Ø   Vice-Director of the Institute of Chemistry, Wrocław University (1991–1993).

Ø   Member of the Editorial Board of Journal of Porphyrin and Phtalocyanines.

Ø   Member of the Editorial Board of European Journal of Inorganic Chemistry.

Ø   Member of the Scientific Board of Centre of Molecular and Macromolecular Studies of the
Polish Academy of Sciences, Łódź.

Ø   Member of the Scientific Council of the Institute of Organic Chemistry of the
Polish Academy of Sciences (1999–2002).


Research staff:

Ø   Prof. Chmielewski Piotr

Ø   Dr. Berlicka Anna

Ø   Dr. Dudziak Ewa

Ø   Dr. Myśliborski Radomir

Ø   Dr. Pawlicki Miłosz

Ø   Dr. Sprutta Natasza

Ø   Dr. Stępień Marcin

Ø   Dr. Szterenberg Ludmiła

Ø   Dr. Wojaczyński Jacek

Ø   Grzegorzek Norbert, M. Sc.

Ø   Maciołek Justyna, M. Sc.

Ø   Nojman Elżbieta, M. Sc.

Ø   Olchówka Monika, M. Sc.

Ø   Simkowa Irena, M. Sc.

Ø   Szyszko Bartosz, M. Sc.



Research topics:


Ø   Carbaporphyrinoids.

Ø   Metalloporphyrins as models for heme enzymes.

Ø   Processes of heme degradation.

Ø   Coordination and organometallic chemistry involving core-modified and expanded porphyrins.

Ø   Reactivity of metalloporphyrin π-cation radicals.

Ø   Oxidation and dioxygen activation by metalloporphyrins.

Ø   Inorganic chemistry of Ni(I).

Ø   Reactivity of covalently linked metalloporphyrins.

Ø   Synthesis of effective photochemothera­peutic agents.

Ø   Electronic structure of inorganic compounds.

Ø   Nuclear magnetic resonance of paramagnetic molecules.



Special equipment:


Ø   Glove-box (MBRAUN) equipped with a LABMASTER 130 Inert Gas System.

Ø   Diode array UV-VIS spectrophotometer Hewlett Packard 8453.

Ø   Equipment for cyclic voltammetry measurements.

Ø   HPLC: analytical and semi-preparative.



Recent research achievements:


1. At present, our research efforts are focused on the synthesis of novel porphyrinoids. These systems differ from regular porphyrins by the replacement of at least one of the pyrrole rings replaced with a carbo- or heterocyclic moiety. These macrocycles can further e transformed into metal complexes. In the case of carbaporphyrinoids, systems with an internally located CH bond, organometallic complexes can form, which exhibit a range of interesting properties.

























2. Carbaporphyrinoids are able to provide unique modes of coordination, such as those exhibited by vacataporphyrin. Vacataporphyrin, [18]triphyrin(4.1.1), yields three coordination modes, which differ in the conformation of the butadiene fragment and in axial ligation. Weak interactions between the metal ion and butadiene moiety can be observed using NMR spectroscopy.




3. Subpyriporphyrin, a homologue of [14]triphyrin(1.1.1), with a pyridine moiety embedded in the macrocyclic framework can be obtained without using boron as a template. Its peculiar structure provides an environment for the shortest N-H···N hydrogen bond ever observed.




Selected papers:


     (1)   Myśliborski, R.; Latos-Grażyński, L.; Szterenberg, L.; Lis, T.
Subpyriporphyrin - a [14]Triphyrin(1.1.1) Homologue With an Embedded Pyridine Moiety.
Chem. Int. Ed. 2006, 45, 3670-3674.     

     (2)   Stępień, M.; Latos-Grażyński, L.; Sprutta, N.; Chwalisz, P.; Szterenberg, L.
Expanded Porphyrin With a Split Personality: A Hückel-Möbius Aromaticity Switch.
Angew. Chem. Int. Ed. 2007, 46, 7869-7874.

     (3)   Pacholska-Dudziak, E.; Skonieczny, J.; Pawlicki, M.; Szterenberg, L.; Ciunik, Z.; Latos-Grażyński, L.
Palladium Vacataporphyrin Reveals Conformational Rearrangements Involving
Hückel and Möbius Macrocyclic Topologies.
J. Am. Chem. Soc. 2008, 130, 6182-6195.

     (4)   Grzegorzek, N.; Pawlicki, M.; Szterenberg, L.; Latos-Grażyński, L.
Organocopper(II) Complex of 21-Diphenylphosphoryl-Carbaporpholactone Hybrid - A Side-on Coordination Mode of Copper(II).
J. Am. Chem. Soc. 2009, 131, 7224-7225.

     (5)   Berlicka, A.; Latos-Grażyński, L.
An Intramolecular Rotation of Iron(II) Dithiaethyneporphyrin Double-Decker Complex - 1H NMR Studies.
Inorg. Chem. 2009, 48, 7922-7930.

     (5)   Grzegorzek, N.; Pawlicki, M.; Latos-Grażyński, L.
Regioselective Amination of Carbaporpholactone.
J. Org. Chem. 2009, 74, 8547-8553.

     (7)   Chmielewski, P. J.; Durlej, B.; Siczek, M.; Szterenberg, L.
Helical Bis(N-Confused Porphyrins) With Subunits Fused by Double Orthometalation With Platinum: Adaptability of an Apparently Rigid System.
Angew. Chem. Int. Ed. 2009, 48, 8736-8739.

     (8)   Sprutta, N.; Maćkowiak, S.; Kocik, M.; Szterenberg, L.; Lis, T.; Latos-Grażyński, L. Tetraazuliporphyrin Tetracation.
Angew. Chem. Int. Ed. 2009, 48, 3327-3341.

     (9)   Stępień, M.; Szyszko, B.; Latos-Grażyński, L.
Three-Level Topology Switching in a Molecular Möbius Band.
J. Am. Chem. Soc. 2010, 132, 3140-3152.

   (10)   Wojaczyński, J.; Latos-Grażyński, L.
Photooxidation of N-Confused Porphyrin a Route to N-Confused Biliverdin Analogs.
Chem. Eur. J. 2010, 16, 2679-2682.