期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 10, 页码 5066-5076出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00423
关键词
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资金
- Ministry of Science and Technology, Taiwan [101-2113-M-001-006-MY3]
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 ftuorophenanthro- 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.
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