Phenanthroline

Colorless crystalline powder

Fixed

• 93-94 ° C ( hydrate)
• 117 ° C ( anhydrous)

Soluble in water (3.3 g · l-1 at 20 ° C) in ethanol and acetone

Risk

132 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Phenanthroline (phen) is formally a derivative of phenanthrene in which two carbon- to are replaced nitrogen atoms.

Representation

Phenanthroline can be represented according to the Skraupschen synthesis by heating 8 - aminoquinoline or o- phenylenediamine with glycerol, nitrobenzene and concentrated sulfuric acid.

Use

In the complex chemistry, it is used as a bidentate ligand with the abbreviation phen use. The best known phenanthroline complexes and ferroin Ferrocyphen in which iron (iron (II) - or iron (III ) ions ) is the central atom. Ferroin is used as a redox indicator use.

The heavy metal complexes of phenanthroline are suitable because of their low solubility for quantitative analysis, methyl - and phenyl -substituted derivatives such as bathocuproine and bathophenanthroline have an even higher selectivity.

Phenanthroline complexes as substrates for the construction of supramolecular systems and the study of those properties, such as using the electron or photoelectron transfer.

In asymmetric homogeneous reactions catalyzed by chiral phenanthroline derivatives are used as ligands.

Biological Properties

Photosynthesis and carboxypeptidases are inhibited by 1,10- phenanthroline. The substance and its metal complexes intercalate into DNA. Since the metal complexes act as metallo analogues, they are used in biochemical research as diagnostic tools.