Max Coehlo, Lucas Frédéric, Laurélie Poulard, Nawal Ferdi, Lilian Estaque, Alaric Desmarchelier, Gilles Clavier, Jean-Pierre Dognon, Ludovic Favereau, Michel Giorgi, Jean-Valère Naubron, Grégory Pieters
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引用次数: 0
摘要
最近,动态手性控制已成为设计手性功能材料的有力策略。在此背景下,我们介绍了一种分子设计,其中的系留构型稳定的双萘手性单元可有效控制供体-受体荧光团的动态手性,包括作为电子供体的各种吲哚咔唑和作为电子受体的对苯二甲腈。密度泛函理论计算表明,这种分子体系具有很高的构象分辨能力,我们利用电子和振动圆二色性进行了实验探测,并通过这些手性分子在凝胶中的结晶及其单晶 X 射线衍射分析证实了这一点。除了将动态手性控制的范围扩展到供体-受体荧光团之外,这项工作还强调了构型稳定的手性感应器通过手性扰动对活性动态手性荧光团基态和激发态不对称因子大小的积极影响。
Control of Dynamic Chirality in Donor-Acceptor Fluorophores
Very recently, the control of dynamic chirality has emerged as a powerful strategy to design chiral functional materials. In this context, we describe herein a molecular design in which a tethered configurationally stable binaphthyl chiral unit efficiently controls the dynamic chirality of donor-acceptor fluorophores, involving diverse indolocarbazoles as electron donors and terephthalonitrile as an electron acceptor. The high conformational discrimination in such a molecular system suggested by density functional theory calculations is experimentally probed using electronic and vibrational circular dichroism and confirmed by the crystallization of these chiral molecules in gel and their single crystal X-ray diffraction analysis. In addition to extending the scope of dynamic chirality control to donor-acceptor fluorophores, this work also highlights the positive effect of the configurationally stable chiral inductor on the magnitude of the dissymmetry factors of the active dynamically chiral fluorophores, both in ground and excited states, through chiral perturbation.
期刊介绍:
Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.