α-Oligofurans: Molecules Without a Twist
α-Oligofurans: Molecules Without a Twist
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DOI：
10.1002/chin.201042257
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发表时间：
2010-10
期刊：
影响因子：
--
通讯作者：
U. Bunz
中科院分区：
文献类型：
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作者：
U. Bunz
有机电子学是研究π共轭有机化合物及其应用的科学，是化学、材料科学和工程领域的研究热点。尽管已经有成千上万的π共轭化合物可用，但新材料的开发是至关重要的，因为在固态中很难获得特定的性能（如稳定性，溶解度，高纯度，在固态中最大化分子间相互作用的分子填充，以及正确的前沿分子轨道水平）。通过引入烷基或烷氧基链来增强溶解度将改变填充并影响分子构象，但也可能破坏π -π相互作用，导致分子间相互作用减少，而添加供体或受体取代基将影响有机半导体的总体电子性质。取代α-低聚和α-聚噻吩[1-3]和并戊烯[4,5]及C60衍生物[6]对有机薄膜晶体管和光伏的发展具有重要意义以噻吩基材料为例，已报道了任何尺寸的低聚物以及具有不同侧链密度、立体化学和区域化学的聚合物的合成路线。然而，性噻吩1几乎完全不溶于一般的有机溶剂1的单晶样品只能通过高真空/高温升华得到虽然六聚体1在固态中是平面的，但低聚和多噻吩在溶液中采用扭曲构象，这可以通过它们通常宽且无特征的吸收光谱来证明。[10-12]关于低硫噻吩的文章已经发表了1000多篇，关于多硫噻吩的文章已经发表了4600多篇，但是相应的聚呋喃类却很少受到关注。大多数关于聚呋喃的出版物都涉及到通过电解三元呋喃单体的电化学合成。由于呋喃、双呋喃和三呋喃的氧化电位有很大的不同
Organic electronics, the science of π-conjugated organic compounds and their applications, is a focus of chemistry, materials science, and engineering. Despite the thousands of π-conjugated compounds that are already available, the development of new materials is critical, as specifically desired properties (such as stability, solubility, high purity, molecular packing to maximize intermolecular interactions in the solid state, and the correct level of the frontier molecular orbitals) are difficult to obtain in the solid state. Enhanced solubility by introduction of alkyl or alkoxy chains will change packing and influence molecular conformation, but might also disrupt π–π interactions, leading to decreased intermolecular interactions, whereas the addition of donor or acceptor substituents will influence the gross electronic properties of organic semiconductors.Substituted α-oligo-and α-polythiophenes,[1–3] and pentacenes [4, 5] and C60 derivatives [6] are important for the development of organic thin-film transistors and photovoltaics.[7] In the case of thiophene-based materials, synthetic routes for oligomers of any size and also polymers with varying sidechain density, stereochemistry, and regiochemistries have been reported. However, the sexithiophene 1 is already almost completely insoluble in common organic solvents.[8] A single-crystal specimen of 1 could only be obtained through high-vacuum/high-temperature sublimation.[9] Whereas hexamer 1 is planar in the solid state, oligo-and polythiophenes adopt twisted conformations in solution, as can be attested to by their normally broad and featureless absorption spectra.[10–12] There have been more than 1000 articles published on oligothiophenes, and more than 4600 articles have been published on polythiophenes, but the corresponding polyfurans have attracted much less attention. Most publications dealing with polyfurans involve the electrochemical synthesis by electrolysis of the terfuryl monomer. As the oxidation potentials of furan, bifuryl, and terfuryl are very different, the