具有桥连 1,4-亚萘基作为框架分子转子的二氮杂大环的合成与旋转动力学。
Synthesis and rotational dynamics of diazamacrocycles having bridged 1,4-naphthylene as framed molecular rotors.
机构信息
Division of Applied Chemistry, Faculty of Urban Environmental Sciences, Tokyo Metropolitan University, 1-1 Minami-Osawa, Hachioji, Tokyo 192-0397, Japan.
Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan.
出版信息
Org Biomol Chem. 2022 Nov 9;20(43):8465-8470. doi: 10.1039/d2ob01613c.
The rotation of a part of a molecule has attracted attention because of its possible role in the development of an artificial molecular rotor. In this study, 1,4-naphthylene bridged diazamacrocycles, in which the 1,4-diaminonaphthalene moiety is bridged by two long alkyl chains, were designed as novel framed molecular rotors, and the dependence of the rotation on the frame size were investigated. Framed rotors CnNp ( = 12, 14, 16, 18), where the number in the compound name indicates the length of a side chain, were synthesized by direct cyclization of 1,4-naphthalenediamine with α,ω-dihaloalkane in the presence of NaCO as the base. The rotation of the naphthylene rotor in C12Np, C14Np, and C16Np was nearly suppressed in solution, whereas the rotor in C18Np showed rotation, as confirmed by the temperature-dependent coalescence of the NMR signals of the α-CH.
分子的一部分的旋转引起了人们的关注，因为它可能在人工分子转子的发展中发挥作用。在这项研究中，设计了 1,4-亚萘基桥联二氮杂大环，其中 1,4-二氨基萘部分由两条长链烷基桥接，作为新型框架分子转子，并研究了其旋转对框架尺寸的依赖性。通过 1,4-萘二胺与α,ω-二卤代烷在 NaCO 作为碱的存在下直接环化，合成了框架转子 CnNp（=12、14、16、18），化合物名称中的数字表示侧链的长度。在溶液中，C12Np、C14Np 和 C16Np 中的亚萘基转子的旋转几乎被抑制，而 C18Np 中的转子则显示出旋转，这通过 NMR 信号的温度依赖性α-CH 峰的合并得到证实。
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