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Self-Assembly and Circularly Polarized Luminescence from Achiral Pyrene-Adamantane Conjugates by Selective Inclusion with Cyclodextrins
The Journal of Physical Chemistry Letters ( IF 4.8 ) Pub Date : 2021-08-03 , DOI: 10.1021/acs.jpclett.1c02013 Chenchen Yang 1, 2 , Wenjie Chen 1, 2 , Xuefeng Zhu 1 , Xin Song 1 , Minghua Liu 1, 2
The Journal of Physical Chemistry Letters ( IF 4.8 ) Pub Date : 2021-08-03 , DOI: 10.1021/acs.jpclett.1c02013 Chenchen Yang 1, 2 , Wenjie Chen 1, 2 , Xuefeng Zhu 1 , Xin Song 1 , Minghua Liu 1, 2
Affiliation
The interaction between guest chromophores or lumiphores with host chiral cavity and their induced chirality is an important topic in supramolecular chemistry. Kodaka and Harata proposed a rule to explain the induced circular dichroism of the guest chromophores by host cyclodextrins. However, it remains unknown how a circularly polarized luminescence (CPL) signal will change when the lumiphores interacted with cyclodextrins in different modes. Here, we designed an achiral pyrene-adamantane conjugated guest molecule, N-(pyren-1-yl)adamantane-1-carboxamide (ACNP), and investigated its interactions with α/β/γ-cyclodextrins (CDs) and its induced CPL. Depending on the size match of the pyrene, adamantine with different cyclodextrins, distinct performance was observed. While α-CD could not induce a CPL signal of ACNP, β-CD could induce CPL in two modes, through adamantyl or direct pyrenyl induction, which could produce a CPL signal with opposite signs. γ-CD could always induce a negative CPL signal. Therefore, a rule of induced CPL of lumiphores by cyclodextrins can be proposed.
中文翻译:
环糊精选择性包合非手性芘-金刚烷共轭物的自组装和圆偏振发光
客体发色团或发光团与主体手性腔及其诱导手性之间的相互作用是超分子化学中的一个重要课题。Kodaka 和 Harata 提出了一个规则来解释宿主环糊精诱导客体发色团的圆二色性。然而,当荧光团以不同模式与环糊精相互作用时,圆偏振发光 (CPL) 信号将如何变化仍然未知。在这里,我们设计了一种非手性芘-金刚烷共轭客体分子N-(pyren-1-yl)adamantane-1-carboxamide (ACNP),并研究其与 α/β/γ-环糊精 (CD) 的相互作用及其诱导的 CPL。根据芘、金刚烷与不同环糊精的大小匹配,观察到不同的性能。虽然α-CD不能诱导ACNP的CPL信号,但β-CD可以通过金刚烷基或直接芘基诱导两种模式诱导CPL,这可以产生符号相反的CPL信号。γ-CD 总是可以诱导负 CPL 信号。因此,可以提出环糊精诱导荧光团CPL的规则。
更新日期:2021-08-12
中文翻译:
环糊精选择性包合非手性芘-金刚烷共轭物的自组装和圆偏振发光
客体发色团或发光团与主体手性腔及其诱导手性之间的相互作用是超分子化学中的一个重要课题。Kodaka 和 Harata 提出了一个规则来解释宿主环糊精诱导客体发色团的圆二色性。然而,当荧光团以不同模式与环糊精相互作用时,圆偏振发光 (CPL) 信号将如何变化仍然未知。在这里,我们设计了一种非手性芘-金刚烷共轭客体分子N-(pyren-1-yl)adamantane-1-carboxamide (ACNP),并研究其与 α/β/γ-环糊精 (CD) 的相互作用及其诱导的 CPL。根据芘、金刚烷与不同环糊精的大小匹配,观察到不同的性能。虽然α-CD不能诱导ACNP的CPL信号,但β-CD可以通过金刚烷基或直接芘基诱导两种模式诱导CPL,这可以产生符号相反的CPL信号。γ-CD 总是可以诱导负 CPL 信号。因此,可以提出环糊精诱导荧光团CPL的规则。