Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan.
Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan.
Molecules. 2022 Aug 11;27(16):5103. doi: 10.3390/molecules27165103.
Spiro-fused polycyclic aromatic compounds (PACs) have received growing interest as rigid chiral scaffolds. However, furan-containing spiro-fused PACs have been quite limited. Here, we design spiro[indeno[1,2-][1]benzofuran-10,10'-indeno[1,2-][1]benzothiophene] as a new family of spiro-fused PACs that contains a furan unit. The compound was successfully synthesized in enantiopure form and also transformed to its ,-dioxide derivative and the pyrrole-containing analog via aromatic metamorphosis. The absorption and emission properties of the obtained furan-containing chiral spiro-fused PACs are apparently different from those of their thiophene analogs that have been reported, owing to the increased electron-richness of furan compared to thiophene. All of the furan-containing chiral spiro-fused PACs were found to be circularly polarized luminescent materials.
螺环稠合多环芳烃（PACs）作为刚性手性支架受到越来越多的关注。然而，含呋喃的螺环稠合 PACs 相当有限。在这里，我们设计了螺[茚并[1,2-][1]苯并呋喃-10,10'-茚并[1,2-][1]苯并噻吩]作为一类新的含有呋喃单元的螺环稠合多环芳烃。该化合物以对映纯的形式成功合成，并且还通过芳构变形转化为其,-二氧化物衍生物和含吡咯的类似物。与已报道的噻吩类似物相比，由于呋喃比噻吩具有更高的电子富度，因此所得到的含呋喃手性螺环稠合多环芳烃的吸收和发射性质明显不同。所有含呋喃的手性螺环稠合多环芳烃均被发现为圆偏振发光材料。
