Zhou Chuanqiang, Ren Yuanyuan, Han Jie, Gong Xiangxiang, Wei Zhixiang, Xie Ju, Guo Rong
Testing Center , Yangzhou University , Yangzhou , Jiangsu 225002 , P. R. China.
School of Chemistry and Chemical Engineering , Yangzhou University , Yangzhou , Jiangsu 225002 , P. R. China.
J Am Chem Soc. 2018 Aug 1;140(30):9417-9425. doi: 10.1021/jacs.7b12178. Epub 2018 Jul 19.
The fabrication of supramolecular chiral nanostructures from achiral materials without the need of pre-existing chirality is a major challenge associated with the origin of life. Herein, supramolecular chiral twisted nanoribbons of achiral oligoaniline derivatives were prepared via simply performing the chemical oxidation of aniline in an alcohol/water mixed solvent. In particular, the supramolecular chirality of the twisted nanoribbons could be controlled by facilely tuning the alcohol content in the mixed solvent. A tetra-aniline derivative CHON was attested to be the major component of the obtained nanoribbons. The main driving forces for the assembly of the oligoaniline derivative into twisted nanoribbons might be the π-π stacking and hydrogen bonding interactions among the chains which could be modulated by the alcohol content in the mixed solvent. The single-handed twisted nanoribbons could be used to separate chiral phenylalanine from a racemic mixture. Thus, it is highly anticipated that the supramolecular chirality endows π-conjugated molecules with potential application in chiral recognition.
从非手性材料制备超分子手性纳米结构而无需预先存在的手性是与生命起源相关的一个主要挑战。在此，通过在醇/水混合溶剂中简单地进行苯胺的化学氧化，制备了非手性低聚苯胺衍生物的超分子手性扭曲纳米带。特别地，扭曲纳米带的超分子手性可以通过轻松调节混合溶剂中的醇含量来控制。一种四苯胺衍生物CHON被证明是所得纳米带的主要成分。低聚苯胺衍生物组装成扭曲纳米带的主要驱动力可能是链间的π-π堆积和氢键相互作用，这可以通过混合溶剂中的醇含量来调节。单手扭曲纳米带可用于从外消旋混合物中分离手性苯丙氨酸。因此，人们高度期望超分子手性赋予π共轭分子在 chiral recognition 中的潜在应用。 （注：“chiral recognition”直译为“手性识别”，这里保留英文未翻译，因为原文可能是特定专业术语，需要结合更多背景信息准确翻译，仅根据现有文本，无法准确给出更合适的中文表述）
