Ultracycles consisting of macrocycles

Presented here is a one-pot strategy starting from rationally designed macrocyclic precursors for the diverse construction of sophisticated ultracycles. The type and amount of the base were found to significantly influence the macrocyclization outcome. The use of 4.0 equiv. CsF resulted in ultracycl...

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Veröffentlicht in:Chinese chemical letters Jg. 35; H. 5; S. 109077 - 188
Hauptverfasser: Mi, Wen-Hui, Huang, Teng-Yu, Ao, Yu-Fei, Wang, Xu-Dong, Wang, Qi-Qiang, Wang, De-Xian
Format: Journal Article
Sprache:Englisch
Veröffentlicht: Elsevier B.V 01.05.2024
University of Chinese Academy of Sciences,Beijing 100049,China%Beijing National Laboratory for Molecular Sciences,CAS Key Laboratory of Molecular Recognition and Function,Institute of Chemistry,Chinese Academy of Sciences,Beijing 100190,China
Beijing National Laboratory for Molecular Sciences,CAS Key Laboratory of Molecular Recognition and Function,Institute of Chemistry,Chinese Academy of Sciences,Beijing 100190,China
Schlagworte:
Anion recognition
Anion–π interaction
Diversity-oriented synthesis
Ultracycles
Anion recognition
Anion–π interaction
Diversity-oriented synthesis
Ultracycles
Anion-π interaction
ISSN:1001-8417, 1878-5964
Online-Zugang:Volltext
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Zusammenfassung:Presented here is a one-pot strategy starting from rationally designed macrocyclic precursors for the diverse construction of sophisticated ultracycles. The type and amount of the base were found to significantly influence the macrocyclization outcome. The use of 4.0 equiv. CsF resulted in ultracycles of both types A and B while the presence of CsF larger than 6.0 equiv. produced only type B ultracycles. Existence of anion template increased the total yields and affected the distribution of the ultracycles. The ultracycles can accommodate large organic dicarboxylates anions via multiple anion–π and hydrogen bonds, and show selectivity to the size-matched heptanedioate (C72−). Based on all possible species and relevant equilibrium constants as well as material and charge balances, a numerical iterative algorithm was developed and applied to fit the association constants of B2H with dicarboxylates from glutarate (C52−) to octanedioate (C82−), which gave association constants up to 103 L/mol. [Display omitted] Functional ultracycles consisting of macrocycles were constructed through a one-pot strategy. The ultracycles showed diverse binding modes towards organic dicarboxylates.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2023.109077