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Steric Control over the Threading of Pyrophosphonates with One or Two Cyanostar Macrocycles during Pseudorotaxane Formation.
Vogel, Julian; Chen, Yusheng; Fadler, Rachel E; Flood, Amar H; von Delius, Max.
Afiliación
  • Vogel J; Institute of Organic Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081, Ulm, Germany.
  • Chen Y; Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, IN, 47405, USA.
  • Fadler RE; Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, IN, 47405, USA.
  • Flood AH; Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, IN, 47405, USA.
  • von Delius M; Institute of Organic Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081, Ulm, Germany.
Chemistry ; 29(41): e202300899, 2023 Jul 20.
Article en En | MEDLINE | ID: mdl-37156722
The supramolecular recognition of anions is increasingly harnessed to achieve the self-assembly of supramolecular architectures, ranging from cages and polymers to (pseudo)rotaxanes. The cyanostar (CS) macrocycle has previously been shown to form 2 : 1 complexes with organophosphate anions that can be turned into [3]rotaxanes by stoppering. Here we achieved steric control over the assembly of pseudorotaxanes comprising the cyanostar macrocycle and a thread that is based, for the first time, on organo-pyrophosphonates. Subtle differences in steric bulk on the threads allowed formation of either [3]pseudorotaxanes or [2]pseudorotaxanes. We demonstrate that the threading kinetics are governed by the steric demand of the organo-pyrophosphonates and in one case, slows down to the timescale of minutes. Calculations show that the dianions are sterically offset inside the macrocycles. Our findings broaden the scope of cyanostar-anion assemblies and may have relevance for the design of molecular machines whose directionality is a result of relatively slow slipping.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2023 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Alemania

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2023 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Alemania