Alkane lengths determine encapsulation rates and equilibria

Academic Article

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Overview

authors

• Jiang, W.
• Ajami, Dariush
• Rebek Jr., Julius

publication date

• 2012

journal

• Journal of the American Chemical Society  Journal

abstract

• A cylindrical capsule provides an environment for straight-chain alkanes that can properly fill the space through extended or compressed conformations. The encapsulation rates of a series of alkanes were examined and found to be dependent on guest length: the rates of uptake are C(9) > C(10) > C(11), while complex stability is in the reverse order, C(11) > C(10) > C(9). Direct competition experiments, pairwise or between all 3 alkanes, maintain this order as the longer alkanes sequentially displace the shorter ones. The distribution of species with time provides a clock for this complex system, which combines elements of self-sorting phenomena and dynamic combinatorial chemistry. The clock can be stopped by replacing the alkanes with the superior guest 4,4'-dimethylazobenzene, then restarted by irradiation.

subject areas

• Alkanes
• Capsules
• Dimerization
• Ethers, Cyclic
• Kinetics
• Models, Molecular
• Molecular Conformation
• Resorcinols
• Thermodynamics

Identity

International Standard Serial Number (ISSN)

• 0002-7863

Digital Object Identifier (DOI)

• 10.1021/ja302669y

PubMed ID

• 22548529

Additional Document Info

start page

• 8070

end page

• 8073

volume

• 134

issue

• 19