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Triphenylamine[3]arenes: Streamlining Synthesis of a Versatile Macrocyclic Platform for Supramolecular Architectures and Functionalities.

Angewandte Chemie International Edition(2024)

Tianjin Univ | Nanyang Technol Univ | Xiamen Univ

Cited 2|Views10
Abstract
Triphenylamine[3]arenes (TPA[3]s), featuring [16]paracyclophane backbone with alternating carbon and nitrogen bridging atoms, were synthesized through a BF3·Et2O‐catalyzed cyclization reaction using triphenylamine derivatized monomers and paraformaldehyde. This molecular design yielded a series of TPA[3] macrocycles with high efficiency, with their facile derivatizations also successfully demonstrated. On account of the strong electron‐donating properties of the TPA moieties, these TPA[3]s exhibit remarkable delayed fluorescence, and possess a significant affinity for iodine. Furthermore, their inherent three‐fold symmetry rendered TPA[3]s as novel building blocks for the construction of extended frameworks and molecular cages. This advancement expands the versatility of discrete macrocycles into complex architectures, enhancing their applicability across a broad spectrum of applications.
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Macrocycle,Triphenylamine[3]arene,Iodine adsorption,Thermally-activated delayed fluorescent,Molecular cages and frameworks
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要点】:本文报道了三苯胺[3]芳环(TPA[3]s)的合成方法,并展示了其在超分子架构和功能中的应用,创新点在于其高效的合成策略以及独特的电子性质和三重对称性所带来的新型建筑块功能。

方法】:通过BF3·Et2O催化的环化反应,利用三苯胺衍生的单体和甲醛,合成了具有[16]位对位环状骨架的TPA[3]大环分子。

实验】:实验使用了三苯胺衍生物单体和甲醛,通过上述方法合成了TPA[3]大环,并对其进行了衍生化验证。合成的TPA[3]大环展示了延迟荧光特性,并对碘有显著的亲和力,同时其三重对称性使其成为构建扩展框架和分子笼的新颖构建块。实验结果证实了TPA[3]s在复杂结构中的多功能性。具体的数据集名称在文中未提及。