Molecular Wires with Controllable π-Delocalization Incorporating Redox-Triggered π-Conjugated Switching Units.,ChemPlusChem

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Molecular Wires with Controllable π-Delocalization Incorporating Redox-Triggered π-Conjugated Switching Units.
ChemPlusChem ( IF 3.0 ) Pub Date : 2018-08-24 , DOI: 10.1002/cplu.201800341
Wataru Nojo ₁ , Hitomi Tamaoki ₁ , Yusuke Ishigaki ₁ , Ryo Katoono ₁ , Kenshu Fujiwara ₂ , Takanori Fukushima ₃ , Takanori Suzuki ₁

Affiliation

A perfluorobiphenyl-2,2'-diyl dication and its corresponding dihydrophenanthrene-type electron donor are interconvertible upon two-electron transfer. Redox-triggered C-C bond-formation/cleavage caused a drastic change in the torsion angle of the biphenyl unit. Thus, π-delocalization ON/OFF switching was observed as a change in the UV absorption upon electrolysis of the linearly extended analogue with two phenylethynyl groups. A further extended π-system with a molecular length of ca. 3.5 nm, which has two switching units, was synthesized. Spectroelectrograms as well as voltammetric analyses showed that the two units act nearly simultaneously because of the very small inter-unit electrostatic repulsion in the tetracationic state. Thus, the present pair is a promising candidate as a switching unit for "molecular wires" with controllable π-delocalization, in which a higher ON/OFF ratio of delocalization could be realized by incorporating multiple switching units.

中文翻译：

具有可控π-离域并结合氧化还原触发的π-共轭开关单元的分子线。

全氟联苯-2,2'-二基阳离子和其相应的二氢菲型电子供体在两电子转移后可相互转化。氧化还原触发的CC键形成/断裂导致联苯单元的扭转角发生急剧变化。因此，观察到π-离域开/关切换是在电解具有两个苯基乙炔基的线性延伸类似物时UV吸收的变化。分子长度为ca的进一步扩展的π系统。合成了具有两个开关单元的3.5 nm。频谱图和伏安分析表明，这两个单元几乎同时起作用，因为在四阳离子状态下，单元间的静电排斥力很小。因此，本对作为“分子线”的开关单元是有前途的候选者

更新日期：2018-08-24

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