Cis-dicarbonyl binding at cobalt and iron porphyrins with saddle-shape conformation

Nature Chemistry

Volumn 3, Issue 2, 2011, Pages 114-119

  Seufert, Knud ^a   Bocquet, Marie Laure ^b   Auwärter, Willi ^a   Weber Bargioni, Alexander ^c   Reichert, Joachim ^a,c   Lorente, Nicolás ^d   Barth, Johannes V ^a,c  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITÉ DE LYON   (France)

^c UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^d CATALAN INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY ICN2   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79251634974     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.956     Document Type: Article

References (34)

1. Spiro, T. G. & Kozlowski, P. M. Is the CO Adduct of myoglobin bent, and does it matter? Acc. Chem. Res. 34, 137-144 (2001).
2. Collman, J. P., Boulatov, R., Sunderland, C. J. & Fu., L. Functional analogues of cytochrome c oxidase, myoglobin, and hemoglobin. Chem. Rev. 104, 561-588 (2004).
3. Ghosh, A. Metalloporphyrin-NO bonding: building bridges with organometallic chemistry. Acc. Chem. Res. 38, 943-954 (2005).
4. Hoard, J. L. Stereochemistry of hemes and other metalloporphyrins. Science 174, 1295-1302 (1971).
5. Kratky, C. et al. The saddle conformation of hydroporphinoid nickel(II) complexes: structure, origin, and stereochemical consequences. Helv. Chim. Act. 68, 1312-1327 (1985).
6. Barkigia, K. M., Chantranupong, L., Smith, K. M. & Fajer, J. Structural and theoretical models of photosynthetic chromophores. Implications for redox, light absorption properties and vectorial electron flow. J. Am. Chem. Soc. 110, 7566-7567 (1988).
7. Barkigia, K. M. et al. Nonplanar porphyrins. X-ray structures of (2,3,7,8,12,13,17,18-octaethyl- and -octamethyl-5,10,15,20- tetraphenylporphinato) zinc(II). J. Am. Chem. Soc. 112, 8851-8857 (1990).
8. Sparks, L. D. et al. Metal dependence of the nonplanar distortion of octaalkyltetraphenylporphyrins. J. Am. Chem. Soc. 115, 581-592 (1993).
9. Shelnutt, J. A. et al. Nonplanar porphyrins and their significance in proteins. Chem. Soc. Rev. 27, 31-41 (1998).
10. Senge, M. O. Exercises in molecular gymnastics-bending, stretching and twisting. Chem. Commun. 243-256 (2006).
11. Weber-Bargioni, A. et al. Visualizing the frontier orbitals of a conformationally adapted metalloporphyrin. ChemPhysChem 9, 89-94 (2008).
12. Auwärter, W. et al. Site-specific electronic and geometric interface structure of Co-tetraphenyl-porphyrin layers on Ag(111). Phys. Rev. B 81, 245403 (2010).
13. Springer, B. A., Sligar, S. G., Olson, J. S. & Phillips, G. N. Jr. Mechanisms of ligand recognition in myoglobin. Chem. Rev. 94, 699-714 (1994).
14. Aono, S. Biochemical and biophysical properties of the CO-sensing transcriptional activator CooA. Acc. Chem. Res. 36, 825-831 (2003).
15. Kim, H. P., Ryter, S. W. & Choi, A. M. K. CO as a cellular signaling molecule. Annu. Rev. Pharmacol. Toxicol. 46, 411-449 (2006).
16. Kachalova, G. S., Popov, A. N. & Bartunik, H. D. A steric mechanism for inhibition of CO binding to heme proteins. Science 284, 473-476 (1999).
17. Sigfridsson, E. & Ryde, U. On the significance of hydrogen bonds for the discrimination between CO and O2 by myoglobin. J. Biol. Inorg. Chem. 4, 99-110 (1999).
18. Leu, B. M. et al. Quantitative vibrational dynamics of iron in carbonyl porphyrins. Biophys. J. 92, 3764-3783 (2007).
19. Madura, P. & Scheidt, W. R. Stereochemistry of low-spin cobalt porphyrins. 8. a,b,g,d-Tetraphenylporphinatocobalt(II). Inorg. Chem. 15, 3182-3184 (1976).
20. Auwärter, W. et al. Controlled metalation of self-assembled porphyrin nanoarrays in two dimensions. ChemPhysChem 8, 250-254 (2007).
21. Meyer, G., Neu, B. & Rieder, K. H. Controlled lateral manipulaiton of single molecules with the scanning tunneling microscope. Appl. Phys. A 60, 343-345 (1995).
22. Lee, H. J. & Ho,W. Single-bond formation and characterization with a scanning tunneling microscope. Science 286, 1719-1722 (1999).
23. Auwärter, W. et al. Molecular nanoscience and engineering on surfaces. Int. J. Nanotechnol. 5, 1171-1193 (2008).
24. Brand, H. & Arnold, J. Recent developments in the chemistry of early transition metal porphyrin compounds. Coord. Chem. Rev. 140, 137-168 (1995).
25. Smith, P. D., James, B. R. & Dolphin, D. H. Structural aspects and coordination chemistry of metal porphyrin complexes with emphasis on axial ligand binding to carbon donors and mono- and diatomic nitrogen and oxygen donors. Coord. Chem. Rev. 39, 31-75 (1981).
26. Wahl, P. et al. Kondo effect of molecular complexes at surfaces: ligand control of the local spin coupling. Phys. Rev. Lett. 95, 166601 (2005).
27. Flechtner, K., Kretschmann, A., Steinrück, H. P. & Gottfried, J. M. NO-induced reversible switching of the electronic interaction between a porphyrincoordinated cobalt ion and a silver surface. J. Am. Chem. Soc. 129, 12110-12111 (2007).
28. Barth, J. V. Fresh perspectives for surface coordination chemistry. Surf. Sci. 603, 1533-1541 (2009).
29. Kresse, G. & Joubert, D. From ultrasoft pseudopotentials to the projector augmented-wave method. Phys. Rev. B 59, 1758-1775 (1999).
30. Mercurio, G. et al. Structure and energetics of azobenzene on Ag(111): benchmarking semiempirical dispersion correction approaches. Phys. Rev. Lett. 104, 036102 (2010).
31. Vladimirova, M. et al. Substrate-induced supramolecular ordering of functional molecules: theoretical modelling and STM investigation of the PEBA/Ag(111) system. Acta Mater. 52, 1589-1596 (2004).
32. Rohlfing, M., Temirov, R. & Tautz, F. S. Adsorption structure and scanning tunneling data of a prototype organic-inorganic interface: PTCDA on Ag(111). Phys. Rev. B 76, 115421 (2007).
33. Klappenberger, F. et al. Conformational adaptation in supramolecular assembly on surfaces. ChemPhysChem 8, 1782-1786 (2007).
34. Franke, K. J. et al. Reducing the molecule-substrate coupling in C60-based nanostructures by molecular interactions. Phys. Rev. Lett. 100, 036807 (2008).