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 bottom-up modular construction of chemically and structurally well-defined oligo(arylfuran)s by de novo synthesis of α,β′-bifuran monomers and late-stage bromination, stannylation and subsequent coupling reaction. The preliminary study of the photophysical properties demonstrated that the polarity-sensitive fluorescence emission and high quantum yields in THF solution 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. Meanwhile, the experimental studies and calculations showed that tetrafurans have appropriate HOMO energy levels, and could therefore potentially be high-performance p-type semiconductors.
Highlights
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
We report the realization of this design of bottomup modular construction of chemically and structurally welldefined oligo(arylfuran)s by de novo synthesis of α,β′-bifuran monomers and late-stage bromination, stannylation, and subsequent coupling reaction (Fig. 1d)
Single-crystal X-ray analyses revealed that the steric-hindrance effect between aryl groups and neighboring furan rings disrupted the planarity of backbone of these oligo(arylfuran)s, but there still have manipulating space in achieving slight twist oligo(arylfuran) s in terms of the crystal data of 4F7
Summary
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. The preliminary study of the photophysical properties demonstrated that the polarity-sensitive fluorescence emission and high quantum yields in THF solution 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. It is about 20 years later from the seminal synthesis of the β,β-oligofuran (8F, R = SiR'3) by Song and Wong[20], an iterative cross-coupling synthesis of similar oligofuran (8F, R = Br) was achieved and revealed its 3D conformation by Paddon-Row and colleagues[21] (Fig. 1b). As Bendikov and colleagues[18] observed in the 16F-6C6 and nF-
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