Chiroselective electron transfer at enantiomer-capped ZnO nanocrystalline surfaces

Chiral Cryptands Possessing Tetraazamacrocyclic and BINAM Moieties: Synthesis and Evaluation as Fluorescent Detectors

“…[14,15] The analogue of BINOL, 2,2'-diamino-1,1'-binaphthalene (BINAM) was shown to be efficient for a-phenylethylamine enantiomers sensing, [16] however, unlike for BINOL, only scarce data can be found in literature considering its derivatives used as fluorescent detectors. [17][18][19] We began our own investigations aimed at the synthesis of BINAMcontaining macrocycles and their use in fluorescent enantioselective detection of amino alcohols. [20][21][22] The present work deals with the synthesis of cryptands on the basis of tetraazamacrocycles comprising endocyclic BINAM moiety.…”

Enantioselective Adsorption of Phenylalanine onto Self-Assembled Monolayers of 1,1‘-Binaphthalene-2,2‘-dithiol on Gold

“…Because such a specific “screw” structure with a supramolecular size is considered to be desirable for catching and discriminating guest organic molecules, SAMs of BNSH are expected to be useful for fabricating sensors for chiral discrimination. Indeed, modification with binaphthyl-derivatives was reported to induce enantioselectivity in electron transfer at ZnO-nanocrystallite surfaces . We report here the enantioselective adsorption of chiral amino acid, d - and l -phenylalanine (Phe), onto ( R )- and ( S )-BNSH SAM, which was monitored by using a quartz crystal microbalance (QCM).…”

Synthesis and Evaluation of the (S)-BINAM Derivatives as Fluorescent Enantioselective Detectors

“…The closest nitrogen-containing analogue of BINOL, 1,1 -binapthalene-2,2 -diamine (BINAM), was shown to be efficient in the recognition of α-phenylethylamine enantiomers [31] quite long ago, but since then, it has not been developed further, unlike BINOL. Among the scarce and random applications of this molecule, one may cite the attempts to recognize tryptophan enantiomers using free BINAM [32], its combination with two residues of chiral thiourea to sense enantiomers of mandelic acid [33], and the synthesis of chiral polymers on the basis of BINOL and BINAM for the detection of phenylalanine [34]. Taking this fact into consideration, we decided to develop the synthesis of BINAM-containing detectors using palladium-catalyzed amination reactions, which have become a powerful tool for creating C(sp 2 )-N bonds in last two decades [35][36][37].…”