Oxygen- and Nitrogen-Embedded Zigzag Hydrocarbon Belts
Mei-Ling Tan
Key Laboratory of Green Chemistry and Technology (MOE), College of Chemistry, Sichuan University, Chengdu, 610064 China
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Qing-Hui Guo
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Xue-Yuan Wang
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorTan-Hao Shi
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorDr. Qian Zhang
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorSheng-Kai Hou
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorProf. Dr. Shuo Tong
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorProf. Dr. Jingsong You
Key Laboratory of Green Chemistry and Technology (MOE), College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Mei-Xiang Wang
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorMei-Ling Tan
Key Laboratory of Green Chemistry and Technology (MOE), College of Chemistry, Sichuan University, Chengdu, 610064 China
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Qing-Hui Guo
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Xue-Yuan Wang
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorTan-Hao Shi
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorDr. Qian Zhang
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorSheng-Kai Hou
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorProf. Dr. Shuo Tong
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorProf. Dr. Jingsong You
Key Laboratory of Green Chemistry and Technology (MOE), College of Chemistry, Sichuan University, Chengdu, 610064 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Mei-Xiang Wang
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (MOE), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorGraphical Abstract
Bridging all fjords of resorcin[4]arene derivatives by means of a macrocyclic-conformation-facilitated intramolecular nucleophilic substitution reaction and palladium-catalyzed intermolecular C−N cross-coupling led to the production of unprecedented oxygen- and nitrogen-doped zigzag hydrocarbon belts (see structure). The heteroatom-embedded belts exhibited markedly different photophysical and redox properties to those of their hydrocarbon analogues.
Abstract
Despite the aesthetically appealing structures and tantalizing physical and chemical properties, zigzag hydrocarbon belts and their heteroatom-embedded analogues remain challenging synthetic targets. We report herein the synthesis of diverse O/N-doped zigzag hydrocarbon belts based on selective bridging of the fjords of resorcin[4]arene derivatives through intramolecular SNAr and palladium-catalyzed intermolecular C−N bond formation reactions. Preorganized conformations of mono-macrocyclic, half-belt and quasi-belt compounds were revealed to facilitate cyclization reactions to construct heteroatom-linked octahydrobelt[8]arenes. The acquired products had strained square-prism-shaped belt structures in which all six-membered heterocyclic rings adopted an unusual boat conformation with equatorially configured alkyl groups. The unprecedented heteroatom-bearing belts also exhibited different photophysical and redox properties to those of octahydrobelt[8]arene analogues.
Conflict of interest
The authors declare no conflict of interest.
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