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Probing Peripheral H-Bonding Functionalities in BN-Doped Polycyclic Aromatic Hydrocarbons

机译:BN掺杂多环芳烃中的概率外周H键合功能

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The replacement of carbon atoms at the zigzag periphery of a benzo[fg]tetracenyl derivative with an NBN atomic triad allows the formation of heteroatom-doped polycyclic aromatic hydrocarbon (PAH) isosteres, which expose BN mimics of the amidic NH functions. Their ability to form H-bonded complexes has never been touched so far. Herein, we report the first solution recognition studies of peripherally NBN-doped PAHs to form H-bonded DD center dot AA- and ADDA center dot DAAD-type complexes with suitable complementary H-bonding acceptor partners. The first determination of K-a in solution showed that the 1:1 association strength is around 27 +/- 1 M-1 for the DD center dot AA complexes in C6D6, whereas it rises to 1820 +/- 130 M-1 for the ADDA center dot DAAD array in CDCl3. Given the interest of BN-doped polyaromatic hydrocarbons in supramolecular and materials chemistry, it is expected that these findings will open new possibilities to design novel materials, where the H-bonding properties of peripheral NH hydrogens could serve as anchors to tailor the organizational properties of PAHs.
机译:在Z字形的苯并的周[FG]并四用NBN原子三联体衍生物置换碳原子的杂原子的允许掺杂的多环芳香烃(PAH)等排体,其中暴露的酰胺NH功能BN模拟物的形成。它们形成氢键络合物的能力从未至今感动。在本文中,我们报道外周NBN掺杂多环芳烃第一溶液识别的研究,以形成H-粘结DD中心点AA-和ADDA中心点DAAD型配合物的合适的互补氢键受体的合作伙伴。嘉在溶液中的第一确定结果表明,1:1的关联强度是约27 +/- 1 M-1为在C6D6的DD中心点AA络合物,而它上升到1820 +/- 130 M-1的ADDA中心点DAAD阵列在CDCl 3中。鉴于超分子和材料化学BN掺杂多环芳烃的利益,预期的是,这些发现将打开了新的可能性,设计新颖的材料,其中,外围NH的氢的H-粘结性能可以作为锚裁缝的组织特性多环芳烃。

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