Structural characterization of artificial self-assembling porphyrins that mimic the natural chlorosomal bacteriochlorophylls c, d, and e

Teodor Silviu Balaban, Myriam Linke-Schaetzel, Anil D. Bhise, Nicolas Vanthuyne, Christian Roussel, Christopher E. Anson, Gernot Buth, Andreas Eichhöfer, Keir Foster, G. Garab, Hartmut Gliemann, Richard Goddard, Tamas Javorfi, Annie K. Powell, Harald Rösner, Thomas Schimmel

Research output: Contribution to journalArticle

67 Citations (Scopus)

Abstract

We report two crystal structures of a synthetic porphyrin molecule which was programmed for self-assembly. The same groups which ensure that bacteriochlorophylls c, d, and e can self-assemble into the chlorosomal nanorods, the photosynthetic antenna system of some green bacteria, have been engineered into desired positions of the tetrapyrrolic macrocycle. In the case of the 5,15-meso-substituted anchoring groups, depending upon the concentration, by using the same crystallization solvents, either a tetragonal or a layered structure of porphyrin stacks were encountered. Surprinsingly, π-π interactions combined with extensive dispersive interactions, which also encompass cyclohexane, one of the crystallization solvents, win over putative hydrogen bonding. We are aware that our compounds differ considerably from the natural bacteriochlorophylls, but based upon our findings, we now question the hydrogen-bonding network, previously proposed to organize stacks of bacteriochlorophylls. Transmission electron microscopy (TEM), atomic force microscopy (AFM), and small-angle X-ray scattering (SAXS) on various isoraeric compounds support our challenge of current models for the chlorosomal antenna as these show structures, astonishingly similar to those of chlorosomes.

Original languageEnglish
Pages (from-to)2267-2275
Number of pages9
JournalChemistry - A European Journal
Volume11
Issue number8
DOIs
Publication statusPublished - Apr 8 2005

Fingerprint

Bacteriochlorophylls
Porphyrins
Crystallization
Hydrogen bonds
Antennas
Cyclohexane
X ray scattering
Nanorods
Self assembly
Atomic force microscopy
Bacteria
Crystal structure
Transmission electron microscopy
Molecules
bacteriochlorophyll c

Keywords

  • Chlorosomes
  • Porphyrinoids
  • Self-assembly
  • Solid-state structures
  • X-ray diffraction

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Balaban, T. S., Linke-Schaetzel, M., Bhise, A. D., Vanthuyne, N., Roussel, C., Anson, C. E., ... Schimmel, T. (2005). Structural characterization of artificial self-assembling porphyrins that mimic the natural chlorosomal bacteriochlorophylls c, d, and e. Chemistry - A European Journal, 11(8), 2267-2275. https://doi.org/10.1002/chem.200400664

Structural characterization of artificial self-assembling porphyrins that mimic the natural chlorosomal bacteriochlorophylls c, d, and e. / Balaban, Teodor Silviu; Linke-Schaetzel, Myriam; Bhise, Anil D.; Vanthuyne, Nicolas; Roussel, Christian; Anson, Christopher E.; Buth, Gernot; Eichhöfer, Andreas; Foster, Keir; Garab, G.; Gliemann, Hartmut; Goddard, Richard; Javorfi, Tamas; Powell, Annie K.; Rösner, Harald; Schimmel, Thomas.

In: Chemistry - A European Journal, Vol. 11, No. 8, 08.04.2005, p. 2267-2275.

Research output: Contribution to journalArticle

Balaban, TS, Linke-Schaetzel, M, Bhise, AD, Vanthuyne, N, Roussel, C, Anson, CE, Buth, G, Eichhöfer, A, Foster, K, Garab, G, Gliemann, H, Goddard, R, Javorfi, T, Powell, AK, Rösner, H & Schimmel, T 2005, 'Structural characterization of artificial self-assembling porphyrins that mimic the natural chlorosomal bacteriochlorophylls c, d, and e', Chemistry - A European Journal, vol. 11, no. 8, pp. 2267-2275. https://doi.org/10.1002/chem.200400664
Balaban, Teodor Silviu ; Linke-Schaetzel, Myriam ; Bhise, Anil D. ; Vanthuyne, Nicolas ; Roussel, Christian ; Anson, Christopher E. ; Buth, Gernot ; Eichhöfer, Andreas ; Foster, Keir ; Garab, G. ; Gliemann, Hartmut ; Goddard, Richard ; Javorfi, Tamas ; Powell, Annie K. ; Rösner, Harald ; Schimmel, Thomas. / Structural characterization of artificial self-assembling porphyrins that mimic the natural chlorosomal bacteriochlorophylls c, d, and e. In: Chemistry - A European Journal. 2005 ; Vol. 11, No. 8. pp. 2267-2275.
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