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首页> 外文期刊>Chemistry: A European journal >Persistent mixed-valence [(TTF)_2]~(+?) dyad of a chiral bis(binaphthol)-tetrathiafulvalene (TTF) derivative
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Persistent mixed-valence [(TTF)_2]~(+?) dyad of a chiral bis(binaphthol)-tetrathiafulvalene (TTF) derivative

机译：手性双（联萘酚）-四硫富瓦烯（TTF）衍生物的持久混合价[（TTF）_2]〜（+？）二元

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摘要

Mixed-valence dyadic [(TTF)_2]~(+?) (TTF = tetrathiafulvalene) species-the elementary building blocks of organic conductors-are usually too weakly associated to be observed in solution, unless covalently bound in dimers or physically constrained into a cage structure. We demonstrate here that a novel chiral tetrathiafulvalene functionalised with two 1,1′-binaphthol units (1) is able to associate in solution into persistent mixedvalence [(TTF)_2]~(+?) dyadic moieties through a stereospecific recognition pattern. This redox active molecule exhibits different electrochemical and spectroscopic responses, as enantiopure RR, SS or meso isomers, a rare example of a chiral system in which different diastereoisomers do not exhibit the same electrochemical features, with a selective formation of the mixed-valence species in the enantiopure (RR)-1 or (SS)-1 isomers only, whereas the meso form does not show this association ability. A rationale for the selective self-association of the RR and SS enantiomers upon oxidation is provided, based on the different molecular geometries and accessibility of the TTF core toward the formation of the mixed-valence species.
机译：混合价二元体[（TTF）_2]〜（+？）（TTF =四硫富瓦烯）物种-有机导体的基本结构单元-通常太弱地结合而无法在溶液中观察到，除非在二聚体中共价键合或受到物理约束笼状结构。我们在这里证明了一个新颖的手性四硫富富烯具有两个1,1'-联萘酚单元（1）的功能，可以通过立体识别模式在溶液中结合成持久的混合价[（TTF）_2]〜（+？）二元部分。该氧化还原活性分子表现出不同的电化学和光谱响应，例如对映纯RR，SS或内消旋异构体，这是手性系统的罕见实例，其中不同的非对映异构体不具有相同的电化学特征，并且选择性地形成了混合价态物质。仅对映纯（RR）-1或（SS）-1异构体，而内消旋形式没有显示这种缔合能力。根据不同的分子几何结构和TTF核对形成混合价物种的可及性，提供了一种氧化后RR和SS对映异构体选择性自缔合的原理。

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