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 O...

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Published inOrganic letters Vol. 19; no. 7; pp. 1590 - 1593
Main Authors Lu, Yao, Fu, Zhan-Da, Guo, Qing-Hui, Wang, Mei-Xiang
Format Journal Article
LanguageEnglish
Published American Chemical Society 07.04.2017
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Summary: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 C60 and C70 in a virtually nonselective manner, O6-corona­[3]­arene­[3]­tetrazines behaved as selective receptors to complex C70 with K 1:1 values up to (3.98 ± 0.08) × 104 M–1 in toluene.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00409