Synthesis and extension/contraction motion of spiroborate-based double-stranded helicates consisting of substituted oligophenol strands

A new class of ortho- and meta-substituted tetraphenols at the terminal phenyl residues with a biphenylene unit in the middle were synthesized and the effect of the substitution position on the spiroborate-based double-stranded helicate formation with sodium borohydride was investigated. The ortho-substitution considerably hampered the spiroborate formation between the terminal biphenol units and the boron atoms, whereas the meta-substituted oligomers formed a double-stranded helicate bridged by spiroborate groups accommodating a sodium cation in the center, which displayed an extension and contraction motion triggered by the removal and addition of sodium ions in solution. (C) 2011 Elsevier Ltd. All rights reserved.