DOI: 10.1002/anie.199307501. Models for the Photosynthetic Reaction Center—Synthesis and Structure of Porphyrin Dimers with <i>cis</i>‐ and <i>trans</i>‐Ethene and Skewed Hydroxymethylene Bridges

Models for the Photosynthetic Reaction Center—Synthesis and Structure of Porphyrin Dimers with cis‐ and trans‐Ethene and Skewed Hydroxymethylene Bridges

10.1002/anie.199307501

Crossref journal-article

Wiley

Angewandte Chemie International Edition in English (311)

Bibliography

Senge, M. O., Gerzevske, K. R., Vicente, M. G. H., Forsyth, T. P., & Smith, K. M. (1993). Models for the Photosynthetic Reaction CenterâSynthesis and Structure of Porphyrin Dimers with cisâ and transâEthene and Skewed Hydroxymethylene Bridges. Angewandte Chemie International Edition in English, 32(5), 750â753. Portico.

Authors 5

Mathias O. Senge (first)
Kevin R. Gerzevske (additional)
M. Graça H. Vicente (additional)
Timothy P. Forsyth (additional)
Kevin M. Smith (additional)

References 34 Referenced 71

{'key': 'e_1_2_1_1_2', 'first-page': '269', 'volume-title': 'Chlorophylls', 'author': 'Wasilewski M. R.', 'year': '1991'} / Chlorophylls by Wasilewski M. R. (1991)
10.1007/3-540-53257-9_3
10.1002/j.1460-2075.1986.tb04520.x
10.1073/pnas.85.21.7993
10.1021/ja00040a028
10.1021/ja00047a015
10.1021/ja00543a044
10.1021/jo00011a005
10.1021/j100182a012
10.1021/ja00393a007
10.1021/ja00263a011
(b)A.Osuka T.Nagata K.Maruyama Chem. Lett.1991 481. (10.1246/cl.1991.481)
(a)H.Meier Y.Kobuke S.‐I.Kugimiya J. Chem. Soc. Chem. Commun.1989 923; (10.1039/C39890000923)
10.1002/ange.19911030519
10.1002/anie.199105821
10.1021/ja00164a027
(a)P. B.Hitchcock J. Chem. Soc. Dalton Trans.1983 2127; (10.1039/dt9830002127)
(b)M. O.Senge H.Hope K. M.Smith J. Chem. Soc. Perkin Trans. 21993 11.
10.1021/jo00276a047
10.1021/cr00097a007
M. G. H.Vicente K. M.Smith Synlett1990 579; (10.1055/s-1990-21171)
10.1021/jo00014a016
10.1007/BF00519953
10.1007/BF00475323
Crystal structure analyses of thetransdimers proved to be very difficult. Due to the insolubility of4aand4cno crystals were obtained for the Cu and Zn complexes; likewise we have not yet been able to grow crystals of4d. Brown cubes of4bwere obtained from CHCl3/CH3OH. C74H88N8Ni22CHCl3 triclinic space groupP1 a= 10.286(1) b= 12.812(2) c= 14.775(2) Å α = 104.64(1) β = 108.46(1) γ = 95.66(1)° V= 1752.8(7) Å3; data collection at 126 K with CuKαradiation. The structure solution revealed all atoms including two CHCl3molecules of salvation and clearly showed thetransconfiguration of the connecting double bond. However refinement belowR= 0.19 was not possible due to systematic twinning problems.
Characterization of the NiIIcisandtransdimers:4b: m.p. > 300°C; UV/VIS (CH2Cl2): λmax[nm](ϵ) = 414 (1.599 × 105) 488 (30400) 530 (20740) 566 (22760).1H NMR (300 MHz CDCl3 25°C): δ = 9.50 (s 2H meso) 9.48(s 4H meso) 7.66 (s 2H CH  CH) 3.88 (m 16H CH2) 3.76 (q 8H CH2) 3.37 (m br 8H CH2) 1.83 1.82 (t 12H each CH3) 1.75 (t 12H CH3) 1.02 (t 12H CH3).5b: m.p. > 300°C; UV/VIS (CH2Cl2): λmax[nm](ϵ) = 393 (1.682 × 105) 435 (12190) 568 (14650).1H NMR (300 MHz CDCI3 25°C): δ = 9.30 9.05 (s 2H each mesoand CH  CH) 8.06 (s 4H meso) 4.03 3.84 3.75 3.57 3.47 2.89 (m 4H each CH2) 2.60 (s 8H CH2) 1.83 (m 12H CH3) 1.43–1.53 (m 24H CH3) 0.67 (t 12H CH3). Thecisandtransisomers can easily be separated based on solubility properties.
Crystal structure data of5a(crystallized from CH2Cl2/CH3OH): C74H88N8Cu2 Mr= 1216.6 monoclinic space groupP21/n a= 19.208(7) b= 14.672(5) c= 24.170(7) Å β = 111.15(3)° V= 6352(4) Å3 (Z= 4; ρcalcd= 1.271 Mgm−3; μMoKα) = 0.718 mm−1. Data collection on a Siemens R3m/V diffractometer at 130 K with MoKαradiation (λ = 0.71073 Å) and a graphite monochromator; crystal size: 0.52 × 0.32 × 0.21 mm. Patterson synthesis refinement by least‐squares on |F| all atoms refined with anisotropic thermal parameters H atoms incorporated using a riding model R= 0.056 wR= 0.064 S= 1.22; 8040 reflections observed withF> 5.0 σ(F) 2θmax= 55° [14].
Further details of the crystal structure investigations may be obtained from the Fachinformationszentrum Karlsruhe Gesellschaft für wissenschaftlich‐technische Information mbH D‐W‐7514 Eggenstein‐Leopoldshafen 2 on quoting the depository number CSD‐57206 the name of the authors and the journal citation.
10.1007/BFb0036789
R. J.Abraham F.Eivazi H.Pearson K. M.Smith J. Chem. Soc. Chem. Commun.1976 698; (10.1039/c39760000698)
J. Chem. Soc. Chem. Commun.1976 699.
Crystal structure data of6(crystallized from CH2Cl2/CH3OH): C69H80N8O·CH2Cl2 Mr= 1255.7 monoclinic space groupC2/c a= 40.31(2) b= 14.997(7) c= 21.954(11) Å β = 108.60(4)° V= 12 579(10)Å3 Z= 8; (ρcalcd= 1.305 Mg m−3; μMoKα) = 0.735 mm−1. Data collection on a a Syntex P21diffractometer at 130 K with MoKαradiation (λ = 0.71073 Å) and a graphite monochromator; crystal size: 0.35 × 0.22 × 0.11 mm. Patterson synthesis refinement by least‐squares on |F| only metal nitrogen and side chain atoms were refined with anisotropic thermal parameters H atoms incorporated using a riding model one ethyl group and the hydroxyl group were disordered R= 0.122 wR= 0.120 S= 1.45; 5146 reflections observed withF> 2.0 σ(F) 2θmax = 48°[14].
10.1021/ja00230a063
10.1016/1011-1344(92)85150-S

Dates

Type	When
Created	21 years, 7 months ago (Dec. 30, 2003, 5:09 p.m.)
Deposited	1 year, 10 months ago (Oct. 10, 2023, 11:32 a.m.)
Indexed	1 year ago (Aug. 26, 2024, 4:26 a.m.)
Issued	32 years, 3 months ago (May 1, 1993)
Published	32 years, 3 months ago (May 1, 1993)
Published Online	21 years, 8 months ago (Dec. 22, 2003)
Published Print	32 years, 3 months ago (May 1, 1993)

Funders 0

None

BibTeX

@article{Senge_1993, title={Models for the Photosynthetic Reaction Center—Synthesis and Structure of Porphyrin Dimers with cis‐ and trans‐Ethene and Skewed Hydroxymethylene Bridges}, volume={32}, ISSN={0570-0833}, url={http://dx.doi.org/10.1002/anie.199307501}, DOI={10.1002/anie.199307501}, number={5}, journal={Angewandte Chemie International Edition in English}, publisher={Wiley}, author={Senge, Mathias O. and Gerzevske, Kevin R. and Vicente, M. Graça H. and Forsyth, Timothy P. and Smith, Kevin M.}, year={1993}, month=may, pages={750–753} }

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