Macrocycles Based on Phenylacetylene Scaffolding

Phase Separation As a Strategy Toward Controlling Dilution Effects in Macrocyclic Glaser-Hay Couplings

“…In addition, the malonate derived macrocycle 15 was isolated in 63% yield under catalytic conditions. Macrocyclization of aryl substituted alkynes was similarly efficient, as the 16-membered diether 16 was isolated in nearly quantitative yields (98%) under the optimized catalytic conditions …”

“…Macrocyclization of aryl substituted alkynes was similarly efficient, as the 16membered diether 16 was isolated in nearly quantitative yields (98%) under the optimized catalytic conditions. 33 Importantly, in all of the above examples, control reactions whereby the substrates were placed in homogeneous MeOH solution at the identical high concentrations only resulted in complete consumption of the diyne precursors and the formation of polymer products demonstrating that phase separation using transitional metal complexes solubilized in PEG 400 can be exploited to promote efficient macrocyclization of a wide range of diyne macrocycles (8À16) in good to excellent yields (65À98%) at high concentrations.…”

Chiral diversification through the assembly of achiral phenylacetylene macrocycles with a two-fold bridge

“…We have been interested in a design strategy to provide multiple chiral structures through the assembly and double-bridging of achiral components 14–16. Here, we used phenylacetylene macrocycles (PAMs)17 as achiral components for the creation of multiple chiral molecules. The assembly of two rings provides multiple forms (Scheme 1).…”

Synthesis and Electronic Properties of Length-Defined 9,10-Anthrylene–Butadiynylene Oligomers

“…The structures and properties of such compounds are modified by varying the kind and number of arene units, the substitution position, and the kinds of linkers . Fundamental oligomers consisting of phenylene units have been extensively studied from various aspects, and their shapes are strongly dependent on the substitution positions . Because 1,4-phenylene oligomers have characteristic rod shapes and extended π-conjugation, many derivatives have been synthesized to produce functional oligomers such as electronic devices and wires .…”