3 years ago

Programmed Synthesis of Molecular Wires with Fixed Insulation and Defined Length Based on Oligo(phenylene ethynylene) and Permethylated α-Cyclodextrins

Programmed Synthesis of Molecular Wires with Fixed Insulation and Defined Length Based on Oligo(phenylene ethynylene) and Permethylated α-Cyclodextrins
Jun Terao, Yasushi Tsuji, Hiroshi Masai, Tetsuaki Fujihara
The development of new tuning methods for π-conjugated insulated molecular wires with strictly defined axle lengths as well as positions and degrees of macrocycle coverage would provide unprecedented insight into insulation effects in functionalized materials. Herein, iterative reactions of oligo(phenylene ethynylene) (OPE) linked with permethylated α-cyclodextrins were carried out to fabricate insulated molecular wires with a defined length and insulation in desired areas. Insulated OPEs were elongated in a stepwise manner by performing sequential coupling/deprotection reactions. The insulated areas on the OPE units in each expansion step were selectively controlled by means of programmed solvent conditions (high/low polarity). Moreover, a completely insulated OPE (up to a linked [11]rotaxane) with high structural regularity and high covering ratio was synthesized by appropriate tuning of the Pd catalyst and an extension unit bearing a traceless capping unit based on a tert-butyldimethylsilyl group. This strategy may guide the development of the selective synthesis of fully insulated, partially insulated, and uninsulated molecular wires with well-defined lengths and covered/uncovered areas. Word on the wire: A strategy for the synthesis of insulated molecular wires (IMWs) based on oligo(phenylene ethynylene) and permethylated α-cyclodextrins was developed by applying an iterative reaction to rotaxane synthesis, which could strictly control the axle lengths and positions/degrees of coverage with multiple macrocycles (see figure). The precise engineering of IMWs would provide unprecedented materials with highly adjustable properties.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701428

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