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Macrocycle‐Based Charge Transfer Cocrystals with Dynamically Reversible Chiral Self‐Sorting Display Chain Length‐Selective Vapochromism to Alkyl Ketones

Angewandte Chemie(2024)

Beijing National Laboratory for Molecular Sciences

Cited 1|Views14
Abstract
Chirality‐driven self‐sorting plays an essential role in controlling the biofunction of biosystems, such as the chiral double‐helix structure of DNA from self‐recognition by hydrogen bonding. However, achieving precise control over the chiral self‐sorted structures and their functional properties for the bioinspired supramolecular systems still remains a challenge, not to mention realizing dynamically reversible regulation. Herein, we report an unprecedented saucer[4]arene‐based charge transfer (CT) cocrystal system with dynamically reversible chiral self‐sorting synergistically induced by chiral triangular macrocycle and organic vapors. It displays efficient chain length‐selective vapochromism toward alkyl ketones due to precise modulation of optical properties by vapor‐induced diverse structural transformations. Experimental and theoretical studies reveal that the unique vapochromic behavior is mainly attributed to the formation of homo‐ or heterochiral self‐sorted assemblies with different alkyl ketone guests, which differ dramatically in solid‐state superstructures and CT interactions, thus influencing their optical properties. This work highlights the essential role of chiral self‐sorting in controlling the functional properties of synthetic supramolecular systems, and the rarely seen controllable chiral self‐sorting at the solid‐vapor interface deepens the understanding of efficient vapochromic sensors.
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saucer[4]arene,chiral self-sorting,co-crystals,vapochromism,host-guest systems
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要点】:本研究报道了一种具有动态可逆手性自排序特性的新型环状电荷转移共晶体,能够对烷基酮表现出选择性蒸气显色性。

方法】:通过手性三角形大环和有机蒸气的共同作用实现了手性自排序结构的精确控制。

实验】:使用DFT计算和X射线衍射等实验手段,研究了不同烷基酮蒸汽下共晶体的结构变化及其光学性质,实验数据集未在文中明确提及。结果显示,该共晶体系统可根据不同烷基酮蒸汽形成同手性或异手性自排序结构,导致其固态超结构和电荷转移相互作用的显著差异,进而影响其光学性质。