Characterization of crown ethers as macrocyclic elements for rotaxane preparation: a Monte Carlo simulation

Yuk Lung Ha; Arup K. Chakraborty

doi:10.1016/0009-2509(94)e0104-x

Characterization of crown ethers as macrocyclic elements for rotaxane preparation: a Monte Carlo simulation

Yuk Lung Ha, Arup K. Chakraborty

University of California at Berkeley

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Rotaxane synthesis via the statistical method depends upon various geometric considerations such as the ring size of the macrocyclic components. In this paper, we examine the conformational statistics for a series of crown ethers (18-crown-6, 24-crown-8, 30-crown-10, and 36-crown-12) in terms of their average radius, radius of gyration, and intramolecular oxygen-oxygen distances. We conduct NPT Monte Carlo simulations to examine these properties as a function of solvent polarity at 25°C and 1 atmosphere pressure. We find that the crowns are more accessible to statistical threading in water than in carbon tetrachloride from the viewpoint of ring size. However, the macrocycles are more distorted (ellipsoidal) in CCl₄, thus opening up the possibility of preparing rotaxanes where the macrocyles discriminate between linear chains with differently shaped monomers depending upon the solvent used. Results regarding the scaling of the radius of gyration with molecular weight for the cyclic molecules are also presented.

Original language	English
Pages (from-to)	2859-2866
Number of pages	8
Journal	Chemical Engineering Science
Volume	49
Issue number	17
DOIs	https://doi.org/10.1016/0009-2509(94)e0104-x
State	Published - Sep 1994
Externally published	Yes

Bibliographical note

Funding Information:
AcknowledgementsAKC would like to thank Prof. Harry Gibson for bringing this problem to our attention during the US-France Workshop on High Performance Polymers held at Annecy, France in June 1992. Financial support for this work was provided by a Shell Foundation Young Faculty Fellowship to AKC and a University of California Mentor Fellowship to YLH. The authors also thank the San Diego Supercomputer Center and the Pittsburgh Supercomputing Center for generous allocations of Cray computing time

Funding

AcknowledgementsAKC would like to thank Prof. Harry Gibson for bringing this problem to our attention during the US-France Workshop on High Performance Polymers held at Annecy, France in June 1992. Financial support for this work was provided by a Shell Foundation Young Faculty Fellowship to AKC and a University of California Mentor Fellowship to YLH. The authors also thank the San Diego Supercomputer Center and the Pittsburgh Supercomputing Center for generous allocations of Cray computing time

Funders	Funder number
Shell Foundation
University of California

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abstract = "Rotaxane synthesis via the statistical method depends upon various geometric considerations such as the ring size of the macrocyclic components. In this paper, we examine the conformational statistics for a series of crown ethers (18-crown-6, 24-crown-8, 30-crown-10, and 36-crown-12) in terms of their average radius, radius of gyration, and intramolecular oxygen-oxygen distances. We conduct NPT Monte Carlo simulations to examine these properties as a function of solvent polarity at 25°C and 1 atmosphere pressure. We find that the crowns are more accessible to statistical threading in water than in carbon tetrachloride from the viewpoint of ring size. However, the macrocycles are more distorted (ellipsoidal) in CCl4, thus opening up the possibility of preparing rotaxanes where the macrocyles discriminate between linear chains with differently shaped monomers depending upon the solvent used. Results regarding the scaling of the radius of gyration with molecular weight for the cyclic molecules are also presented.",

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year = "1994",

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doi = "10.1016/0009-2509(94)e0104-x",

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PY - 1994/9

Y1 - 1994/9

N2 - Rotaxane synthesis via the statistical method depends upon various geometric considerations such as the ring size of the macrocyclic components. In this paper, we examine the conformational statistics for a series of crown ethers (18-crown-6, 24-crown-8, 30-crown-10, and 36-crown-12) in terms of their average radius, radius of gyration, and intramolecular oxygen-oxygen distances. We conduct NPT Monte Carlo simulations to examine these properties as a function of solvent polarity at 25°C and 1 atmosphere pressure. We find that the crowns are more accessible to statistical threading in water than in carbon tetrachloride from the viewpoint of ring size. However, the macrocycles are more distorted (ellipsoidal) in CCl4, thus opening up the possibility of preparing rotaxanes where the macrocyles discriminate between linear chains with differently shaped monomers depending upon the solvent used. Results regarding the scaling of the radius of gyration with molecular weight for the cyclic molecules are also presented.

AB - Rotaxane synthesis via the statistical method depends upon various geometric considerations such as the ring size of the macrocyclic components. In this paper, we examine the conformational statistics for a series of crown ethers (18-crown-6, 24-crown-8, 30-crown-10, and 36-crown-12) in terms of their average radius, radius of gyration, and intramolecular oxygen-oxygen distances. We conduct NPT Monte Carlo simulations to examine these properties as a function of solvent polarity at 25°C and 1 atmosphere pressure. We find that the crowns are more accessible to statistical threading in water than in carbon tetrachloride from the viewpoint of ring size. However, the macrocycles are more distorted (ellipsoidal) in CCl4, thus opening up the possibility of preparing rotaxanes where the macrocyles discriminate between linear chains with differently shaped monomers depending upon the solvent used. Results regarding the scaling of the radius of gyration with molecular weight for the cyclic molecules are also presented.

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Characterization of crown ethers as macrocyclic elements for rotaxane preparation: a Monte Carlo simulation

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