Synthesis of Butadiynyl-Strapped Corona[6]arenes and Their Selective Anion Binding Properties
A number of butadiynylene-strapped O6-corona[6]arenes were synthesized straightforwardly through intramolecular oxidative homocoupling of O6-corona[6]arenes, which contained at least two N-propargyl-phthalimide segments. The mono-macrocyclic reactants were prepared from the reaction between 3,6-...
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Veröffentlicht in: | Journal of organic chemistry 2020-02, Vol.85 (4), p.2312-2320 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A number of butadiynylene-strapped O6-corona[6]arenes were synthesized straightforwardly through intramolecular oxidative homocoupling of O6-corona[6]arenes, which contained at least two N-propargyl-phthalimide segments. The mono-macrocyclic reactants were prepared from the reaction between 3,6-dichlorotetrazine and N-propargyl-3,6-dihydroxyphthalimide and another 1,4-dihydroxybenzene derivative with roughly a 3:2:1.3–1.5 ratio in a one-pot reaction manner. The synthesized butadiynylene-strapped corona[3]arene[3]tetrazines acted as highly selective electron-deficient macrocyclic hosts to form 1:1 complexes with thiocyanate in solution, and the association constant (K a) was up to 1390 M–1. The anion−π noncovalent interactions provided the driving force for host–guest complexation. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.9b03017 |