Rotationally Hindered Biphenyls and Terphenyls: Synthesis, Molecular Dynamics, and Configurational Assignment.

Sterically hindered naphthalene-substituted biphenyls and terphenyls were synthesized in good yields, by Michael addition of a conjugate base of core-substituted phenylacetones to substituted 2-oxo-2H-pyran-3-carbonitriles at room temperature under alkaline conditions. These diversely functionalized benzenes (1,2-teraryls or 1,3-teraryls), bearing naphthyl and substituted aryl rings, show the phenomenon of atropisomerism, with one or two stereogenic biaryl axes. The resolution of the respective four atropisomers of the naphthalene-substituted biphenyls and terphenyls bearing 1,2-type or 1,3-type chiral biaryl axes was achieved by HPLC on a chiral phase.

A dual colorimetric-ratiometric fluorescent probe NAP-3 for selective detection and imaging of endogenous labile iron(III) pools in C. elegans.

The discovery of an iron(III)-selective ratiometric fluorescent probe to detect and visualize endogenous labile iron pools in living organisms at the molecular level has been long awaited. Herein we report the first dual colorimetric and ratiometric fluorescent probe naphtho[2,1-b][1,10]phenanthroline for selective and 'direct' visualization of labile iron(III) pools in a multicellular organism, Caenorhabditis elegans.

Discovery of biaryl-4-carbonitriles as antihyperglycemic agents that may act through AMPK-p38 MAPK pathway.

A series of functionalized biaryl-4-carbonitriles was synthesized in three steps and evaluated for PTP-1B inhibitory activity. Among the synthesized compounds, four biaryls 6a-d showed inhibition (IC50 58-75 μM) against in vitro PTP-1B assay possibly due to interaction with amino acid residues Lys120, Tyr46 through hydrogen bonding and aromatic-aromatic interactions, respectively. Two biaryl-4-carbonitriles 6b and 6c showed improved glucose tolerance, fasting as well as postprandial blood glucose, serum total triglycerides, and increased high-density lipoprotein-cholesterol in SLM, STZ, STZ-S and C57BL/KsJ-db/db animal models.

Thermally stable nonaggregating pyrenylarenes for blue organic light-emitting devices.

A new series of thermally stable blue light-emitting nonplanar pyrenylarenes having an amine donor and a nitrile acceptor group was prepared from a ketene-S,S-acetal under conventional heating and/or microwave irradiation. The photophysical, electrochemical, and optical behavior of donor-acceptor pyrenylarenes are demonstrated. The performance of blue light-emitting pyrenylarenes was investigated by fabricating a multilayer device with the device configuration of ITO/PEDOT:PSS (40 nm)/NPB (30 nm)/pyrenylarene (55 nm)/BCP (8 nm)/LiF (0.