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首页> 外文期刊>Chemistry: A European journal >Rational construction of perylene bisimide columnar superstructures with a biased helical sense
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Rational construction of perylene bisimide columnar superstructures with a biased helical sense

机译：偏斜螺旋结构of双酰亚胺柱状上部结构的合理构造

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摘要

Discotic supramolecular complexes bearing six perylene bisimide (PBI) chromophores were prepared by mixing monotopically triple-hydrogen-bonding melamines equipped with two PBI chromophores and two 3,7-dimethyloctyl chiral handles with tritopically triple-hydrogen-bonding cyanuric acid (CA). UV/Vis and fluorescence titration experiments demonstrated that the discotic complexes were formed in methylcyclohexane by the 3:1 complexation between the melamines and CA. TEM and AFM studies revealed that the complexes hierarchically organize into fibrous columnar assemblies, which eventually results in the formation of organogels. Circular dichroism (CD) and flash-photolysis time resolved microwave conductivity measurements revealed the presence of extended chiral stacks of PBI chromophores within the columns. The anisotropy factors of the columnar assemblies are remarkably high (g=1.5× 10~(-3)) when considering the presence of only one 3,7-dimethyloctyl chiral handle per perylene chromophore, suggesting that the columnar structures have a biased helical sense. The fact that the chiral centers are located inside the discotic complexes rather than at their peripheries might be unique structural property responsible for the rather strong optical activities for the assemblies of this chromophore. The effective transcription of the molecular chirality to the extended columnar assemblies through the formation of unique discotic complexes enables the expression of "majority-rules" chiral amplification effect, which is unprecedented for the supramolecular assemblies of PBIs.
机译：通过将装备有两个PBI生色团和两个3,7-二甲基辛基手性柄的单位三氢键三聚氰胺与三位三氢键合的氰尿酸（CA）混合，制备带有六个six双酰亚胺（PBI）生色团的盘状超分子复合物。 UV / Vis和荧光滴定实验表明，圆盘状配合物是通过三聚氰胺与CA之间的3：1配合而在甲基环己烷中形成的。 TEM和AFM研究表明，络合物分层组织成纤维状柱状组件，最终导致有机凝胶的形成。圆二色性（CD）和快速光解时间分辨的微波电导率测量结果表明，在色谱柱内存在扩展的手性PBI发色团。当考虑到仅存在一个3,7-二甲基辛基手性per per生色团时，柱状组装体的各向异性因子非常高（g = 1.5×10〜（-3）），这表明柱状结构具有偏斜的螺旋感。手性中心位于盘状复合体内部而不是其周边的事实可能是独特的结构性质，导致该生色团的组件具有相当强的光学活性。通过形成独特的盘状复合物，分子手性有效地转录到延伸的柱状组装体上，从而能够表达“多数规则”的手性扩增效应，这对于PBIs的超分子组装而言是前所未有的。

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