Syntheses of covalently-linked porphyria-quinone complexes. I

Journal Article · Sun Jun 01 04:00:00 EDT 1980 · J. Heterocycl. Chem.; (United States)

DOI:https://doi.org/10.1002/jhet.5570170422· OSTI ID:5067139

Kong, J L.Y.; Loach, P A

A synthetic route for the preparation of covalently-linked prophyin-quinone and metalloporphyrinquinone complexes as models for the phototrap in bacterial photosynthesis is described. 5(5-Carboxyphenyl)-10,15,20-tritolylporphyrin, prepared by a mixed aldehyde approach, was attached to benzoquinone center with a propanediol bridge by means of ester linkages. The starting point for the benzoquinone moiety was 2,5-dihydroxyphenylacetic acid, whose hydroquinone function was first protected by preparing its dimethyl ether. The spacing between the two centers of the complex could be altered simply by varying the length of the bridging group (a diol) employed. Boron tribomide was used to unmask the quinol derivatives in the final coupled products. The zinc(II) derivative of porphyrin-quinone complex was prepared by addition of a saturated solution of zinc acetate in methanol to a solution of the corresponding prophyrin-hydroqyuinone complex in dichloromethane at room temperature. The structures of these complexes were confirmed by nmr spectroscopy, uv-visible absorption, and mass spectroscopy. Oxidation of the quinol moiety in the covalently-linked complex to its corresponding quinonoid derivative was accomplished by treating a solution of the complex in dichloromethane with a stoichiometric amount of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, a high potential benzoquinone.

• Research Organization: Northwestern Univ., Evanston, IL
• OSTI ID: 5067139
• Journal Information: J. Heterocycl. Chem.; (United States), Journal Name: J. Heterocycl. Chem.; (United States) Vol. 17; ISSN JHTCA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400500* -- Photochemistry
550200 -- Biochemistry
550700 -- Microbiology
59 BASIC BIOLOGICAL SCIENCES
ABSORPTION
ACETATES
AROMATICS
BACTERIA
BINDING ENERGY
BORON BROMIDES
BORON COMPOUNDS
BROMIDES
BROMINE COMPOUNDS
CARBOXYLIC ACID SALTS
CARBOXYLIC ACIDS
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CHEMISTRY
CHLOROPHYLL
COMPLEXES
ELECTRONS
ELEMENTARY PARTICLES
ENERGY
FERMIONS
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
LEPTONS
MICROORGANISMS
NMR SPECTRA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHOTOCHEMICAL REACTIONS
PHOTOCHEMISTRY
PHOTOSYNTHESIS
PHOTOSYNTHETIC BACTERIA
PHYTOCHROMES
PIGMENTS
PORPHYRINS
QUINONES
SPECTRA
SYNTHESIS
VALENCE