Synthesis of trivalent flexible frameworks with ligands comprising catechol units for functionalizing surfaces

Abstract

The present invention describes tripodal catechol derivatives with a flexible basic framework for the functionalization of surfaces, and methods for their production and use. The central atom of the flexible framework is hereby a tertiary aliphatic carbon atom. The remaining fourth bridgehead position is easily suitable to be further functionalized via so-called click reactions, e.g. with biomolecules, dyes, radiomarkers, polyethylene glycol or active agents. The compounds according to the present invention have the general formula X—C[(CH)—YZ], wherein X stands for a group —(CH)—R, wherein p=0 to 10 and Ris selected from —H, —NH, —NO, —OH, —SH, —O—NH, —NH—NH, —N═C═S—, —N═C═O—, —CH═CH, —C≡CH, —COOH, —(C═O)H, —(C═O)RY stands for —CH—, —CH═CH—, —C≡C—, —O—, —S—, —S—S—, —NH—, —O—NH—, —NH—O—, —HC═N—O—, —O—N═CH—, —NR—, -Aryl-, -Heteroaryl-, —(C═O)—, —O—(C═O)—, —(C═O)—O—, —NH—(C═O)—, —(C═O)—NH—, —NR—(C═O)—, —(C═O)—NR—, —NH—(C═O)—NH—, —NH—(C═S)—NH—, Rstands for an aryl group, Rfor an alkyl, alkenyl, alkynyl, aryl or heteroaryl group, and Z stands for a catechol derivative. The production of the compounds occurs by reacting a compound X—C[(CH)—Y']with a reagent Y″Z to the corresponding compound X—C[(CH)—YZ]and subsequent purification of the reaction product. Y′ and Y″ are hereby precursors of Y. The compounds according to formula (I) according to the present invention are suitable to be used in a method to functionalize surfaces. The X group of the compounds according to the present invention is suitable to be optionally coupled to an effector, for example, by means of click chemistry.