Ethenetricarboxylic acid diester 1a is a useful compound bearing two reactive sites, a CO2H group and a Michael acceptor. Reactions of 1a and reagents with oxygen and nitrogen nucleophilic moieties have been examined. The reaction of 1a with 2-aminoalcohols in the presence of EDCI and HOBt in one pot gave N,O-containing heterocyclic compounds, regioselectively. The stepwise method has also been...

Covalent tethering of P(Ph)2N(C6H4C≡CH)2 ligands (P(Ph)2N(C6H4C≡CH)2 = 1,5-di-(4-ethynylphenyl)-3,7-diphenyl-1,5-diaza-3,7-diphosphacyclooctane) to planar, azide-terminated glassy carbon electrode surfaces has been accomplished using a Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC) coupling reaction, using a BH3←P protection-deprotection strategy. Deprotected, surface-confined ligands were ...

Submicrometer patterns of adjacent, well-ordered and disordered domains were obtained using optical lithography by area-selective, photoinduced disordering transitions within block copolymer composite films. Enantiopure tartaric acid was blended with poly(ethylene oxide-block-tert-butyl acrylate), PEO-b-PtBA, copolymers to yield well-ordered films. In the presence of triphenylsulfonium triflate...

Hydroxamic acids chelate metals with high affinity and form hydrolytically stable complexes with metal oxides such as TiO2. However, these appealing binding properties can cause problems during the preparation and application of metallocatalysts with appended hydroxamate anchoring groups. Here we show that the tetrahydropyran (THP) O-protected hydroxamate group can be cleaved in situ on a TiO2 ...

While algorithmic DNA self-assembly is, in theory, capable of forming complex patterns, its experimental demonstration has been limited by significant assembly errors. In this paper we describe a novel protection/deprotection strategy to strictly enforce the direction of tiling assembly growth to ensure the robustness of the assembly process. Tiles are initially inactive, meaning that each tile...

A new, highly efficient, all-solid-phase synthesis of argifin, a natural product cyclic pentapeptide chitinase inhibitor, is reported. The synthesis features attachment of an orthogonally protected Asp residue to the solid support and assembly of the linear peptide chain by Fmoc SPPS prior to cyclisation and side-chain manipulation on-resin. Introduction of the key N-methyl carbamoyl-substitute...

A versatile and simple methodology for the creation of mixed monolayers on glassy carbon (GC) surfaces was developed, using an osmium-bipyridyl complex and anthraquinone as model redox probes. The work consisted in the electrochemical grafting on GC of a mixture of mono-protected diamine linkers in varying ratios which, after attachment to the surface, allowed orthogonal deprotection. After opt...

Nanoparticles possessing multiple functionalities provide synthetic handles for varied surface chemistries, making them useful for a range of applications such as biotargeting and drug delivery. However, the combination of interfering functionalities on the same particle is often challenging. We have employed a synthetic scheme involving chemical protection/deprotection to combine interfering f...