SYNTHESIS OF TRIVALENT FLEXIBLE FRAMEWORKS WITH LIGANDS COMPRISING CATECHOL UNITS FOR FUNCTIONALIZING SURFACES

摘要

The present invention relates to tripodal catechol derivatives having a flexible basic framework for functionalizing surfaces, to methods for the production and to the use thereof. The central atom of the flexible frameworks is a tertiary aliphatic carbon atom. The remaining fourth bridgehead position can easily be further functionalized further by so-called click reactions, for example by using biomolecules, dyes, radio markers, polyethylene glycol or active substances. The compounds according to the invention have the general formula X-C[(CH₂)_n-YZ]₃, wherein X represents a group -(CH₂)_p-R⁵, in which p = 0-10 and R⁵ is selected from -H, -NH₂, -NO₂, -OH, -SH, -O-NH₂, -NH-NH₂, -N=C=S-, -N=C=O-, -CH=CH₂, -C=CH, -COOH, -(C=O)H, -(C=O)R⁶, Y represents -CH₂-, -CH=CH-, -C=C-, -O-, -S-, -S-S-, -NH-, -O-NH-, -NH-O-, -HC=N-O-, -O-N=CH-, -NR¹-, -aryl-, -heteroaryl-, -(C=O)-, -O-(C=O)-, -(C=O)-O-, -NH-(C=O)-, -(C=O)-NH-, -NR¹-(C=O)-, -(C=O)-NR¹-, -NH-(C=O)-NH-, -NH-(C=S)-NH-, R¹ represents an alkyl group, R⁶ represents an alkyl, alkenyl, alkinyl, aryl or heteroaryl group and Z represents a catechol derivative. The compounds are produced by reacting a compound X-C[(CH₂)_n-Y']₃ with a reagent Y"Z to form the corresponding compound X-C[(CH₂)_n-YZ]₃ and the reaction product is subsequently purified. Y' and Y'' are precursors of Y. The compounds according to the invention of formula (I) can be used in a method for functionalizing surfaces. Optionally, the group X of the compounds according to the invention can be coupled to an effector, for example by means of click chemistry.