Bottom-up Modular Synthesis of Well-Defined Oligo(arylfuran)s
Abstract Oligofurans have attracted great attention in the field of materials over the last decades because of their several advantages, such as strong fluorescence, charge delocalization, and increased solubility. Although unsubstituted or alkyl substituted oligofurans have been well-established, there is an increasing demand for the development of the aryl decorated oligofuran with structural diversity and unrevealed properties. Here we report the first example of bottom-up modular construction of chemically and structurally well-defined oligo(arylfuran)s by de novo synthesis of α,β'-bifuran monomers and subsequent coupling reaction. Moreover, a preliminary study of the photophysical properties demonstrated that the polarity-sensitive fluorescence emission (up to 530 nm) and ultra-high Stokes shifts (up to 244 nm) could be achieved by modulating the aryl groups on the oligo(arylfuran)s. These twisted molecules constitute a new class of oligofuran backbone useful for structure−activities relationship studies and appear to be promising fluorophores.
