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Symmetry and polar-π effects on the dynamics of enshrouded aryl-alkyne molecular rotors


Karim, A K; Linden, A; Baldridge, K K; Siegel, J S (2010). Symmetry and polar-π effects on the dynamics of enshrouded aryl-alkyne molecular rotors. Chemical Science, 1(1):102-110.

Abstract

The central ring of a 1,4-bis(arylethynyl)arene (ditolan) can be viewed as a molecular rotor with an extremely low barrier to rotation in the gas phase or solution. The torsional energy profile of that ring is shown to be dependent on the relative conformation of the end capping arenes. When the capping arenes are sterically bulky m-terphenyl units, it is possible to rationalize the conformational dynamics of the central ring by a factorization analysis, involving perturbation of the basic torsional energy profile by polar-π, and dispersion interactions between the flanking rings of the cap and the central ring of the ditolan. The symmetry of the construct can modulate the effect of these interactions. These principles apply to the design of materials in which a steric shroud excludes packing distortions.

The central ring of a 1,4-bis(arylethynyl)arene (ditolan) can be viewed as a molecular rotor with an extremely low barrier to rotation in the gas phase or solution. The torsional energy profile of that ring is shown to be dependent on the relative conformation of the end capping arenes. When the capping arenes are sterically bulky m-terphenyl units, it is possible to rationalize the conformational dynamics of the central ring by a factorization analysis, involving perturbation of the basic torsional energy profile by polar-π, and dispersion interactions between the flanking rings of the cap and the central ring of the ditolan. The symmetry of the construct can modulate the effect of these interactions. These principles apply to the design of materials in which a steric shroud excludes packing distortions.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2010
Deposited On:18 Feb 2011 20:01
Last Modified:05 Apr 2016 14:46
Publisher:Royal Society of Chemistry
ISSN:2041-6520
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1039/c0sc00117a
Permanent URL: https://doi.org/10.5167/uzh-45511

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