Chiral V-shaped Pyrenes: Hexagonal Packing, Superhelix, and Amplified Chiroptical Performance,Angewandte Chemie International Edition

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Chiral V-shaped Pyrenes: Hexagonal Packing, Superhelix, and Amplified Chiroptical Performance
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2021-07-01 , DOI: 10.1002/anie.202107842
Song Hu _{1,

2} , Liangyu Hu _{1,

2} , Xuefeng Zhu ₁ , Yuan Wang ₁ , Minghua Liu _{1,

2}

Affiliation

Here, we designed symmetric and dissymmetric chiral V-shaped pyrenes by linking achiral pyrenes to trans-1,2-cyclohexane diamine scaffolds with varied spacers to investigate their circular dichroism (CD) and circularly polarized excimer emission (CPEE). In molecular solution, the symmetric V-shaped molecules (P1, P2, P3) displayed spacer-dependent CD and CPEE originating from the intramolecular excimers while the dissymmetric V-shaped B was silent in CD and CPEE. Upon self-assembly, the chiral V-shaped conformation guided a helical hexagonal packing. Notably, P1 self-assembled into delicate superhelices with optimum chiroptical activities and the largest g_CD for pyrene derivatives to date. The dissymmetric B formed two distinct hexagonal aggregates as twists and rectangular nanotubes with greatly amplified CPEE. This work demonstrates unprecedented hexagonal superhelices from chiral V-shaped scaffolds and provides a deep insight into the relationship between molecular conformation, supramolecular architectures, and their chiroptical performance.

中文翻译：

手性 V 形芘：六边形堆积、超螺旋和放大的手性光学性能

在这里，我们通过将非手性芘与具有不同间隔物的反式-1,2-环己烷二胺支架连接起来，设计了对称和不对称的手性 V 形芘，以研究它们的圆二色性 (CD) 和圆偏振准分子发射 (CPEE)。在分子溶液中，对称V形分子（P1、P2、P3）显示出源自分子内准分子的间隔物依赖性CD和CPEE，而不对称V形B在CD和CPEE中沉默。在自组装时，手性 V 形构象引导螺旋六边形填料。值得注意的是，P1自组装成精细的超螺旋，具有最佳的脊椎活动和最大的g迄今为止芘衍生物的_CD。不对称的B形成两个不同的六边形聚集体作为扭曲和矩形纳米管，CPEE 大大放大。这项工作展示了前所未有的来自手性 V 形支架的六边形超螺旋，并深入了解了分子构象、超分子结构及其手性光学性能之间的关系。

更新日期：2021-08-17

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