O6-Corona[6]arenes with Expanded Cavities for Specific Complexation with C70.
O6-Corona[3]arene[3]tetrazines with expanded cavities were synthesized by one-pot SNAr reaction between 3,6-dichlorotetrazine and aromatic diols. The macrocycle-to-macrocycle transformation involving IEDDA of tetrazine moieties with an enamine followed by denitrogenative aromatization afforded O6-corona[3]arene[3]pyridazines. O6-Corona[6]arenes adopted coronary conformations yielding hexagonal cavities of varied sizes. While O6-corona[3]arene[3]pyridazines complexed both C60and C70in a virtually nonselective manner, O6-corona[3]arene[3]tetrazines behaved as selective receptors to complex C70with K1:1values up to (3.98 ± 0.08) × 104M-1in toluene.
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Tsinghua University , Beijing 100084, China.
Yao
Y
Lu
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Tsinghua University , Beijing 100084, China.
Zhan-Da
ZD
Fu
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Tsinghua University , Beijing 100084, China.
Qing-Hui
0000-0002-9946-0810
QH
Guo
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Tsinghua University , Beijing 100084, China.
Mei-Xiang
0000-0001-7112-0657
MX
Wang