Department of Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
The Institute of Science and Industrial Research (ISIR) Osaka University , 8-1, Mihogaoka, Ibaraki, Osaka 567-0047, Japan.
Org Lett. 2017 Jul 21;19(14):3791-3794. doi: 10.1021/acs.orglett.7b01666. Epub 2017 Jul 13.
A convenient method for the syntheses of dibenzo[h,rst]pentaphenes and dibenzo[fg,qr]pentacenes via the ruthenium-catalyzed chemoselective C-O arylation of 1,4- and 1,5-dimethoxyanthraquinones is described. Dimethoxyanthraquinones reacted selectively with arylboronates at the ortho C-O bonds to give diarylation products. An efficient two-step procedure consisting of a Corey-Chaykofsky reaction and subsequent dehydrative aromatization afforded derivatives of dibenzo[h,rst]pentaphenes and dibenzo[fg,qr]pentacenes. Hole-transporting characteristics were observed for a device with a bottom-contact configuration that was fabricated from one of these polycyclic aromatic hydrocarbons.
通过钌催化的 1,4-和 1,5-二甲氧基蒽醌的化学选择性 C-O 芳基化反应，描述了二苯并[h,rst]戊并菲和二苯并[fg,qr]戊并菲的方便合成方法。二甲氧基蒽醌选择性地与芳基硼酸酯在邻 C-O 键上反应，得到二芳基化产物。一个有效的两步法，包括 Corey-Chaykofsky 反应和随后的脱水芳构化，得到了二苯并[h,rst]戊并菲和二苯并[fg,qr]戊并菲的衍生物。从这些多环芳烃中的一种制备的底接触配置的器件观察到空穴传输特性。
