A versatile approach for the immobilization of amines via copper-free “click” reaction between azido self-assembled monolayer and alkynyl Fischer carbene complex. Application to the detection of staphylococcal enterotoxin A antibody

Recent advances in the field of multicarbene and multimetal carbene complexes of the Fischer-type

“…The engineering of designer surfaces functionalized with carbenes [50,51,[216][217][218], and the redox properties and intervalence charge transfer of such organometallic systems on electrode surfaces [219] are other rapidly expanding focus areas. A class of multimetal multicarbene complexes with great potential includes those with a large number of carbene ligands found in close proximity to each other in macromolecular assemblies or surfaces.…”

“…The extension of carbene cluster chemistry to metal surfaces holds promise for future studies. The engineering of designer surfaces of selfassembled monolayers functionalized with Fischer carbenes for immunosensing [50,51] represents a novel application. Fig.…”

Fischer carbene mediated covalent grafting of a peptide nucleic acid on gold surfaces and IR optical detection of DNA hybridization with a transition metalcarbonyl label

“…All other solvents were used as received. N-succinimidyl 4-pentynoate dicobalt hexacarbonyl (SucPentCo) [16], bis(11-azidoundecyl)disulfide [10], phenylacetylenylethoxycarbene pentacarbonyl tungsten(0) [9,17] and the homothymine monomer aeg-(T)PNA-COOH [18] were synthesized according to the literature. 11-Mercaptoundecanoic acid (MUA), 11bromoundecanethiol…”

“…They are based on the well-known reaction of Fischer metalloalkoxycarbene complexes with amines that affords metalloaminocarbenes in high yield. These alkoxycarbene entities can be introduced either by Ru-catalyzed crossmetathesis reaction between alkene-terminated SAM and alkene containing Fischer carbene [7] or by copper-free 1,3-dipolar cycloaddition reaction ("click reaction") between azideterminated SAM and an alkynyl Fischer carbene [8][9][10]. These strategies were successfully applied to covalently immobilize Protein A and staphylococcal enterotoxin A (SEA) onto gold or glass surfaces by aminolysis involving some of the pendant amino groups of both proteins.…”

Metal‐Free Click Chemistry Reactions on Surfaces

“…However, the reaction conditions need to be optimized, and although the metal is not a catalyst, the reaction is not really metal‐free. Using a similar approach, Sarkar and co‐workers have also immobilized protein A onto gold surfaces, and amine‐containing molecules and proteins onto planar gold‐coated glass sensors ( Figure ) …”