氯[10]环并苯并[def]菲的合成与二聚：直接连接的环并苯并[def]菲二聚体。

Synthesis and dimerization of chloro[10]cycloparaphenylene: a directly connected cycloparaphenylene dimer.

机构信息

Graduate School of Science, ‡JST ERATO, Itami Molecular Nanocarbon Project, and §Institute of Transformative Bio-Molecules (WPI-ITbM) Nagoya University , Chikusa, Nagoya 464-8602, Japan.

出版信息

Org Lett. 2014 Apr 18;16(8):2174-6. doi: 10.1021/ol500643c. Epub 2014 Apr 1.

DOI:10.1021/ol500643c

PMID:24689496

Abstract

The first synthesis and dimerization of monochlorinated [10]cycloparaphenylene (chloro[10]CPP) are described. By assembling a chlorinated 1,4-diborylbenzene unit with brominated and borylated cis-1,4-diphenylcyclohexane units by Suzuki-Miyaura coupling, a triangle-shaped chloro-containing macrocycle was synthesized. The acid-mediated "cyclohexane-to-benzene" aromatization afforded chloro[10]CPP without losing the chloro group. By the action of Ni(0) complex, chloro[10]CPP was converted to a directly connected [10]CPP dimer, which would be an ideal precursor for the "carbon nanobelt".

摘要

首次合成并二聚化了单氯代[10]并苯（氯[10]CPP）。通过 Suzuki-Miyaura 偶联反应，将一个氯代 1,4-二硼基苯单元与溴代和硼代顺式 1,4-二苯基环己烷单元组装在一起，合成了一个三角形的含氯大环。酸介导的“环己烷到苯”芳构化反应在不失去氯基团的情况下得到氯[10]CPP。通过 Ni(0)配合物的作用，氯[10]CPP 转化为直接连接的[10]CPP 二聚体，这将是“碳纳米带”的理想前体。