Axially Chiral Facial Amphiphiles with a Dihydronaphthopentaphene Structure as Molecular Tweezers for SWNTs
Axially Chiral Facial Amphiphiles with a Dihydronaphthopentaphene Structure as Molecular Tweezers for SWNTs
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DOI：
10.1002/chem.200901545
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发表时间：
2009-01-01
影响因子：
4.3
通讯作者：
Wagner, Alain
中科院分区：
文献类型：
--
作者：
Marquis, Renaud;Kulikiewicz, Krystyna;Wagner, Alain
报道了具有相反构型的手性6，15-二氢并[2，3-c]五吩衍生物的合成。从菲开始，该策略包括两个关键步骤：在前手性双蒽醌上进行Diels-Alder反应，以及使用(-)-薄荷醇进行对映体拆分。圆二色谱表明，最终的分子表现出很强的旋光性，是手性面部两亲性的例子。还研究了它们在单壁碳纳米管(SWNTs)表面的吸附，发现在高压CO转化(HIPCO)单壁碳纳米管(0.8-1.2 nm)样品中，它们优先发生在直径为0.8-1.0 nm的纳米管上。合成的面部两亲分子充当纳米镊子，用于选择性地增溶碳纳米管在水中的直径。用圆二色谱研究了每个手性两亲分子增溶的单壁碳纳米管样品的预期光学活性，但结果还不确定。
Syntheses of chiral 6,15-dihydronaphtho[2,3-c]pentaphene derivatives of opposite configurations are reported. Starting from anthracene, the strategy involves two key steps: a Diels-Alder reaction on a prochiral di-anthraquinone, and an enantiomeric resolution using (-)-menthol. The final molecules exhibit very strong optical activity, as shown by their circular dichroism spectra, and are examples of chiral facial amphiphiles. Their adsorption at the surface of single-walled carbon nanotubes (SWNTs) has also been studied, and has been found to occur preferentially on 0.8-1.0 nm diameter nanotubes among the population of a high-pressure CO conversion (HiPco) SWNT sample (0.8-1.2 nm). The synthesised facial amphiphiles act as nano-tweezers for the diameter-selective solubilisation of SWNTs in water. The expected optical activities of the SWNT samples solubilised by each of the chiral amphiphiles have been studied by circular dichroism spectroscopy, but the results are not yet conclusive.