Hamaguchi Naoto, Kubota Takumi, Yamada Masaaki, Kimura Hikaru, Tsuji Hayato
Department of Chemistry, Faculty of Science, Kanagawa University, 3-27-1 Rokkaku-bashi, Kanagawa-ku, Yokohama, 221-8686, Japan.
Chemistry. 2024 Jul 5;30(38):e202400987. doi: 10.1002/chem.202400987. Epub 2024 May 22.
This study explores the synthesis of cyclopenta-fused polyaromatic hydrocarbons (CP-PAHs) via Pt-catalyzed cyclization in water, focusing on the formation of fused pentagonal rings within heavily fused PAH frameworks. Utilizing platinum catalysts at lower temperatures (200-260 °C) in water, led to the successful synthesis of singly cyclized CP-PAHs. The reaction conditions facilitated the mono-cyclization of substrates such as dibenzo[g,p]chrysene and its isomers, yielding the desired products while suppressing the formation of bis-cyclized compounds. The use of FeO as an additive in conjunction with PtO was effective to suppress hydrogenation of the substrates and products. The products exhibited a redshift in UV-visible absorption and photoluminescence bands due to a decrease in the HOMO-LUMO energy gap. These findings highlight the potential of Pt-catalyzed cyclization for the controlled synthesis of CP-PAHs, with implications for various applications in materials science.
本研究探索了在水中通过铂催化环化反应合成环戊稠合多环芳烃（CP-PAHs），重点关注在高度稠合的PAH骨架内形成稠合的五角环。在水中较低温度（200 - 260°C）下使用铂催化剂，成功合成了单环化的CP-PAHs。反应条件促进了底物如二苯并[g,p] Chrysene及其异构体的单环化，生成了所需产物，同时抑制了双环化化合物的形成。将FeO作为添加剂与PtO结合使用有效地抑制了底物和产物的氢化。由于HOMO-LUMO能隙减小，产物在紫外-可见吸收和光致发光带中出现红移。这些发现突出了铂催化环化在CP-PAHs可控合成方面的潜力，对材料科学中的各种应用具有重要意义。
