Iterative synthesis, structures, and properties of acyclic and cyclic acridone oligomers
Iterative synthesis, structures, and properties of acyclic and cyclic acridone oligomers
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无环和环状吖啶酮低聚物的迭代合成、结构和性质
DOI：
10.1002/ajoc.202200508
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发表时间：
2022
影响因子：
2.7
通讯作者：
Shinji Toyota
中科院分区：
文献类型：
--
作者：
Takashi Komori;Eiji Tsurumaki;Shinji Toyota
以10-均三甲苯基吖啶酮作为含杂原子的π共轭化合物，通过迭代法合成了无环和环状吖啶酮-2，7-二基低聚物。通过区域选择性溴化、硼基化、Ni（0）介导的同源偶联和Suzuki-Miyaura偶联的组合将低聚物链延长至无环六聚体。随后，通过溴化和分子内偶联合成了环状六聚体。DFT计算表明，无环低聚物倾向于采用具有反构象的扩展结构，而环状六聚物则采用具有同构象的大环结构。测定了系列低聚物的紫外/维斯光谱和荧光光谱，并从π共轭角度讨论了链长和环化反应的影响。
Acyclic and cyclic acridone‐2,7‐diyl oligomers were synthesized by an iterative procedure from 10‐mesitylacridone as heteroatom containing π‐conjugated compounds. The oligomeric chain was elongated by a combination of regioselective bromination, borylation, Ni(0)‐mediated homocoupling, and Suzuki‐Miyaura coupling up to acyclic hexamer. Subsequently, the cyclic hexamer was synthesized by the bromination and intramolecular coupling of the acyclic hexamer. The DFT calculations revealed that the acyclic oligomers preferred to take extended structures withanticonformations, whereas the cyclic hexamer took a macrocyclic structure withsynconformations. The UV/Vis and fluorescence spectra of the series of oligomers were measured, and the effects of the chain length and the cyclization are discussed in terms of π‐conjugation.