Abstract

The preparation and spectroscopic characterization of some symmetrical small molecules containing the disubstituted (E)-3,3′-bifuranylidene-2,2′-dione chromophore (the so-called Pechmann lactone) and featuring an extended conjugation are reported. The synthetic approach of such compounds is based on the Stille–Migita coupling reaction, which is carried out in very mild conditions, suitable to be applied with the very sensitive Pechmann core. The absorption and emission spectra of the new molecules obtained have been recorded in solution and clearly show how their photophysical properties can be modulated by a proper choice of the (hetero)aromatic terminal groups. The compounds prepared in this study (or close analogues thereof) have interesting optical properties and could find application as semiconductors in organic electronics or as near-IR fluorescent dyes.

The preparation and spectroscopic characterization of some symmetrical small molecules containing the disubstituted (E)-3,3′-bifuranylidene-2,2′-dione chromophore (the so-called Pechmann lactone) and featuring an extended conjugation are reported. The synthetic approach of such compounds is based on the Stille–Migita coupling reaction, which is carried out in very mild conditions, suitable to be applied with the very sensitive Pechmann core. The absorption and emission spectra of the new molecules obtained have been recorded in solution and clearly show how their photophysical properties can be modulated by a proper choice of the (hetero)aromatic terminal groups. The compounds prepared in this study (or close analogues thereof) have interesting optical properties and could find application as semiconductors in organic electronics or as near-IR fluorescent dyes.

中文翻译：

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扩展Pechmann内酯噻吩衍生物的共轭：有机电子应用的一类新的小分子。

摘要

一些含有双取代（E的对称小分子的制备和光谱学表征。）-3,3'-双呋喃基亚砜-2,2'-二酮生色团（所谓的Pechmann内酯）被报道并具有扩展的缀合。此类化合物的合成方法基于Stille–Migita偶联反应，该反应在非常温和的条件下进行，适用于非常敏感的Pechmann核。得到的新的分子的吸收和发射光谱已被记录在溶液中并清楚地示出如何其光物理性质可通过（杂）的适当选择的芳香族末端基团进行调制。这项研究中制备的化合物（或其紧密类似物）具有令人感兴趣的光学性质，可以作为有机电子中的半导体或近红外荧光染料应用。

一些含有双取代（E的对称小分子的制备和光谱学表征。）-3,3'-双呋喃基亚砜-2,2'-二酮生色团（所谓的Pechmann内酯）被报道并具有扩展的缀合。此类化合物的合成方法基于Stille–Migita偶联反应，该反应在非常温和的条件下进行，适用于非常敏感的Pechmann核。得到的新的分子的吸收和发射光谱已被记录在溶液中并清楚地示出如何其光物理性质可通过（杂）的适当选择的芳香族末端基团进行调制。这项研究中制备的化合物（或其紧密类似物）具有令人感兴趣的光学性质，可以作为有机电子中的半导体或近红外荧光染料应用。