Kumar Sushil, Tao Yu-Tai
Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan.
J Org Chem. 2015 May 15;80(10):5066-76. doi: 10.1021/acs.joc.5b00423. Epub 2015 May 1.
The successful iron chloride-catalyzed Scholl reactions toward a series of polyphenylated carbazole derivatives differing in their N-substitution are described. These reactions were found to be compatible over a series of polyaryls possessing fluoro, methoxy, and methyl functional groups, subsequently leading to the synthesis of partially and completely annulated phenanthro- and tetracenocarbazoles in excellent yields. One major consequence of nonsubstitution on carbazolyl-N and the unsymmetrical framework of some of the derivatives is the low solubility of the product; thus, a change from NH- to N-decyl on the carbazole nucleus was carried out. All newly developed derivatives were characterized by spectroscopic techniques, while the chemical structures of fluorophenanthro- and methoxytetracenocarbazoles were confirmed by single-crystal XRD analyses. The present efforts may likely expand the family of growing heteroarenes for future applications as semiconductors and electroluminescent materials.
本文描述了在氯化铁催化下，一系列氮取代不同的多苯基咔唑衍生物成功发生的肖尔反应。研究发现，这些反应与一系列含有氟、甲氧基和甲基官能团的多芳基化合物兼容，随后以优异的产率合成了部分和完全环化的菲并咔唑和并四苯咔唑。咔唑基 -N 未被取代以及某些衍生物的不对称骨架导致的一个主要结果是产物的低溶解度；因此，对咔唑核上的 NH - 变为 N - 癸基进行了改变。所有新开发的衍生物均通过光谱技术进行了表征，而氟代菲并咔唑和甲氧基并四苯咔唑的化学结构通过单晶 X 射线衍射分析得到了证实。目前的研究成果可能会扩大不断增长的杂芳烃家族，以便未来用作半导体和电致发光材料。
