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Molecular Spur Gears Comprising Triptycene Rotators and Bibenzimidazole-Based Stators


Frantz, D K; Linden, A; Baldridge, K K; Siegel, J S (2012). Molecular Spur Gears Comprising Triptycene Rotators and Bibenzimidazole-Based Stators. Journal of the American Chemical Society, 134(3):1528-1535.

Abstract

Dynamic gearing of molecular spur gears, the most common type of mechanical gear, is elucidated. Molecular design and conformational analysis show that derivatives of 4,4-bis(triptycen-9-ylethynyl)bibenzimidazole represent suitable constructs to investigate gearing behavior of collateral triptycene (Tp) groups. To test this design, DFT calculations (B97-D/Def2-TZVP) were employed and the results suggest that these molecules undergo geared rotation preferentially to gear slippage. Synthesis of derivatives was carried out, providing a series of molecular spur gears, including the first desymmetrized spur gear molecules, which were subsequently subjected to stereochemical analysis.

Abstract

Dynamic gearing of molecular spur gears, the most common type of mechanical gear, is elucidated. Molecular design and conformational analysis show that derivatives of 4,4-bis(triptycen-9-ylethynyl)bibenzimidazole represent suitable constructs to investigate gearing behavior of collateral triptycene (Tp) groups. To test this design, DFT calculations (B97-D/Def2-TZVP) were employed and the results suggest that these molecules undergo geared rotation preferentially to gear slippage. Synthesis of derivatives was carried out, providing a series of molecular spur gears, including the first desymmetrized spur gear molecules, which were subsequently subjected to stereochemical analysis.

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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:4 January 2012
Deposited On:02 Apr 2012 07:33
Last Modified:05 Apr 2016 15:31
Publisher:American Chemical Society
ISSN:0002-7863
Publisher DOI:https://doi.org/10.1021/ja2063346

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