Silicon surface biofunctionalization with dopaminergic tetrahydroisoquinoline derivatives

摘要: Abstract In this work we grafted vinyl- and azido-terminated tetrahydroisoquinolines (compounds 1 2 , respectively) onto H Si(1 1 1) silicon wafers obtaining highly stable modified surfaces. A double bond was incorporated into the tetrahydroisoquinoline structure of to be immobilized by a light induced hydrosilylation reaction on hydrogen-terminated Si(1 1 1). The best results were obtained employing polar solvent (DMSO), rather than non-polar (toluene). azide derivative alkenyl-terminated substrates with copper-catalyzed azide-alkyne cycloaddition (CuAAC). Atomic force microscopy (AFM), contact angle goniometry (CA) X-ray photoemission spectroscopy (XPS) used demonstrate incorporation surfaces, study morphology surfaces calculate yield grafting surface coverage. CA measurements showed increase in hydrophobicity when or surface. Moreover, compounds prepared starting from 1-( p -nitrophenyl)tetrahydroisoquinoline 3 under smooth conditions good yields. structures designed reduced A-ring, two substituents at positions C-6 C-7, an N -methyl group phenyl moiety C-1 order provide high affinity against dopaminergic receptors. O -demethylation carried out once it adsorbed treatment BBr . method presented constitutes simple, easily reproducible yielding approach for complex organic biomolecules properties