首页> 外文期刊>Journal of the American Chemical Society >Catalytic Enantioselective Synthesis of Axially Chiral Polycyclic Aromatic Hydrocarbons (PAHs) via Regioselective C-C Bond Activation of Biphenylenes
【24h】

Catalytic Enantioselective Synthesis of Axially Chiral Polycyclic Aromatic Hydrocarbons (PAHs) via Regioselective C-C Bond Activation of Biphenylenes

机译:通过联苯的区域选择性C-C键活化,催化手性合成轴向手性多环芳烃(PAHs)

获取原文
获取原文并翻译 | 示例
获取外文期刊封面目录资料

摘要

Chiral polycyclic aromatic hydrocarbons (PAHs) are expected to have unusual physical properties due to their chirality and expanded π-conjugated system. Indeed, PAHs are promising compounds as chiral recognizers and organic semiconductors. Therefore, an efficient method for the synthesis of chiral PAHs is strongly desired. In contrast to helically chiral PAHs, there are only limited examples of the enantioselective synthesis of axially chiral PAHs. Herein, we report the catalytic enantioselective synthesis of benzo[b]fluoranthene-based axially chiral PAHs in excellent yields and enantioselectivities (up to >99%, >99% ee) by regioselective cleavage of the sterically hindered C-C bond of biphenylenes. The consecutive cyclizations could provide polycyclic PAHs with two chiral axes. The obtained chiral PAHs have high e values (up to ε = 8.9 × 10~4), quantum yields (up to Φ = 0.67), and circularly polarized luminescence (CPL) property (lg_(lum)l = up to 3.5 X 10~(-3)).
机译:由于手性多环芳烃(PAHs)的手性和扩展的π共轭体系,它们有望具有不同寻常的物理性质。实际上,多环芳烃作为手性识别剂和有机半导体是很有前途的化合物。因此,强烈需要合成手性PAHs的有效方法。与螺旋手性PAH相反,轴向手性PAH的对映选择性合成仅是有限的例子。在这里,我们报告了苯并[b]荧蒽基轴向手性多环芳烃的催化对映选择性合成,通过区域选择性裂解联苯的C-C键的区域选择性裂解,具有极高的收率和对映选择性(最高> 99%,> 99%ee)。连续的环化可以提供具有两个手性轴的多环PAH。获得的手性PAH具有高e值(高达ε= 8.9×10〜4),量子产率(高达Φ= 0.67)和圆偏振发光(CPL)特性(lg_(lum)l =高达3.5 X 10) 〜(-3))。

著录项

  • 来源
    《Journal of the American Chemical Society》 |2020年第10期|4714-4722|共9页
  • 作者单位

    Department of Chemistry and Biochemistry School of Advanced Science and Engineering Waseda University Shinjuku Tokyo 169-8SSS Japan;

    Department of Chemistry and Biochemistry School of Advanced Science and Engineering Waseda University Shinjuku Tokyo 169-8555 Japan;

    Department of Applied Chemistry Faculty of Science and Engineering Kindai University Higashi-Osaka Osaka 577-8502 Japan;

    Global Center of Science and Engineering School of Advanced Science and Engineering Waseda University Shinjuku Tokyo 169-8555 Japan;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱:kefu@zhangqiaokeyan.com

京公网安备:11010802029741号 ICP备案号:京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有
  • 客服微信

  • 服务号