Summary of the technology
Ruthenium (II) photocatalysts of formula (M +) nXn- are described, in which Xn- is an anion and M + is a cationic complex of formula (Ia) comprising an 8-arylsulfonamidoquinoline ligand, as well as its method of obtaining it. The use of said ruthenium (II) photocatalysts in the synthesis of imines by photooxidation of amines in the presence of oxygen and by the use of visible light is also described.
Description of the technology
New and innovative aspects
The procedure for the synthesis of mono-cationic complexes of Ru (II) of the polypyridine type described, presents activity as photocatalysts despite not being considered as good candidates for photocatalysis according to the state of the art. Specifically, the Ru (II) complexes of the invention have a superior stability to the equivalent photocatalysts known in the state of the art, such as ruthenium (II) complexes of the type, [Ru (bipi) 3] 2+ .
Furthermore, the ruthenium (II) complexes of the invention provide a high yield for the conversion of amines to imines (greater than 90%), with very good selectivity and without producing undesired by-products. This imine synthesis procedure is performed in the presence of O2 by irradiating with visible light at room temperature, between 20-30 oC.
Main advantages of its use
•Conversions of benzylamine to imine with yields greater than 90% and without additives, at room temperature and with the use of oxygen or air as an oxidizing agent.
• The use of visible light allows synthesis to be carried out with substrates more sensitive to over-oxidation or the degradation of their products by photoactivation of bonds, avoiding the formation of unwanted secondary products.
• Present a photostability equal to or greater than that of the analogous complexes of the state of the art of ruthenium (II) of the formula [Ru (bipi) 3] 2+.
• More selective procedure and with optimal yields.
Design of new Ru(II) photosensitizers bearing 8-arylsulfonamidoquinolines and the successful evaluation of their photocatalytic properties in a new method the smooth and selective oxidation of primary and secondary benzylamines using O2 as the oxidant.
In this proposed method three key features must be highlighted: the photosensitizing ability of the Ru(II) complexes that promotes the production of O2; the electrophilic nature of O2 that facilitates its reaction with nucleophilic amines and the weak acidic character of the in situ generated H2O2 that assists in the catalytic activation of the primary aldimine.
- Synthesis of new drugs and diagnosis due to their interaction with DNA.
- Acting as luminophores in Bioimaging techniques (cell visualization).
- Photodynamic Therapy (PDT). Some of these Ru (II) complexes are known for their cytotoxic activity after irradiation with light, generating highly reactive singlet oxygen that causes cell death.
- Photocatalysis acting as photosensitizers (PS) in synthetic organic reactions or in hydrogen production.
- Electroluminescent devices such as LED emission diodes, including OLED (Organic Light Emiting Diodes) type.
- Obtaining Sulfóxidos from the oxidation of sulfides of application in the obtaining of different drugs.
Intellectual property status
Protected by patent P202030245.
Current development status
The technology related to the synthesis method is developed.
Desired business relationship
Commercial agreement; License agreement; Technical cooperation: further development; Technical cooperation: testing new applications; Technical cooperation: adaptation to specific needs.
Intellectual property status