95752-88-8Relevant academic research and scientific papers
Rhenium bipyridine complexes for the recognition of glucose
Cary, Douglas R.,Zaitseva, Natasha P.,Gray, Kelsey,O'Day, Kira E.,Darrow, Christopher B.,Lane, Stephen M.,Peyser, Thomas A.,Satcher Jr., Joe H.,Van Antwerp, William P.,Nelson,Reynolds, John G.
, p. 1662 - 1669 (2008/10/08)
Bipyridine ligands containing pendant methyl, amino, and amino-boronic acid groups were synthesized. Coordination complexes of these ligands with rhenium were prepared straightforwardly and in good yield. The fluorescence behavior of the Re complexes was studied as a function of pH and exposure to various concentrations of glucose. The methyl bipyridine complex showed no change in fluorescence with pH, the amino derivative showed a rapid decrease from low pH to neutral, and the amino-boronate derivative showed little change from pH 4 to 10. Fluorescence quenching was observed at high pH as expected on the basis of a photoinduced electron transfer (PET) signaling mechanism. This behavior can be explained on the basis of the first oxidation and reduction potentials of these complexes. Glucose testing showed a significant dependence on the solvent system used. In pure methanol, the rhenium boronate complex exhibited a 55% fluorescence intensity increase upon increasing glucose concentration from 0 to 400 mg/dL However, in 50 vol % methanol/phosphate buffered saline, none of the complexes showed significant response in the glucose range of physiological interest.
ARYLBORONIC ACIDS WITH INTRAMOLECULAR B-N INTERACTION: CONVENIENT SYNTHESIS THROUGH ortho-LITHIATION OF SUBSTITUTED BENZYLAMINES
Lauer, Manfred,Wulff, Guenter
, p. 1 - 10 (2007/10/02)
Ortho-lithiation of N,N-dimethylbenzylamine and reaction with trimethylborate gave the corresponding boronic acid in good yields.The reaction was extended to the synthesis of various aromatic boron compounds with nitrogen-containing substituents in the ortho-position, including a chiral boroxin prepared from (S)-N,N-dimethyl-1-phenylethylamine.From N-Methyl-benzylamine a stable boronium salt was obtained under certain conditions.The spectra of the newly synthesized compounds are discussed.Intramolecular B-N interaction is established by 11B NMR spectroscopy.
