Article | Published:

Unidirectional rotary motion in achiral molecular motors

Nature Chemistry volume 7, pages 890896 (2015) | Download Citation

Abstract

Control of the direction of motion is an essential feature of biological rotary motors and results from the intrinsic chirality of the amino acids from which the motors are made. In synthetic autonomous light-driven rotary motors, point chirality is transferred to helical chirality, and this governs their unidirectional rotation. However, achieving directional rotary motion in an achiral molecular system in an autonomous fashion remains a fundamental challenge. Here, we report an achiral molecular motor in which the presence of a pseudo-asymmetric carbon atom proved to be sufficient for exclusive autonomous disrotary motion of two appended rotor moieties. Isomerization around the two double bonds enables both rotors to move in the same direction with respect to their surroundings—like wheels on an axle—demonstrating that autonomous unidirectional rotary motion can be achieved in a symmetric system.

  • Compound C25H22

    (R,P)-9-(2,4,7-trimethyl-2,3-dihydro-1H-inden-1-ylidene)-9H-fluorene

  • Compound C25H22

    (S,M)-9-(2,4,7-trimethyl-2,3-dihydro-1H-inden-1-ylidene)-9H-fluorene

  • Compound C38H28

    9,9'-((s,P,M)-2,4,7-trimethyl-1H-indene-1,3(2H)-diylidene)bis(9H-fluorene)

  • Compound C39H30

    9,9'-(2,2,4,7-tetramethyl-1H-indene-1,3(2H)-diylidene)bis(9H-fluorene)

  • Compound C38H27F

    9,9'-((s,P,M)-2-fluoro-2,4,7-trimethyl-1H-indene-1,3(2H)-diylidene)bis(9H-fluorene)

  • Compound C38H27F

    9,9'-((r,P,M)-2-fluoro-2,4,7-trimethyl-1H-indene-1,3(2H)-diylidene)bis(9H-fluorene)

  • Compound C38H27F

    9,9'-((M,M)-2-fluoro-2,4,7-trimethyl-1H-indene-1,3(2H)-diylidene)bis(9H-fluorene)

  • Compound C38H27F

    9,9'-((P,P)-2-fluoro-2,4,7-trimethyl-1H-indene-1,3(2H)-diylidene)bis(9H-fluorene)

  • Compound C40H31FO2

    9,9'-((r,1-(E,P),3-(E,M))-2-fluoro-2,4,7-trimethyl-1H-indene-1,3(2H)-diylidene)bis(2-methoxy-9H-fluorene)

  • Compound C40H31FO2

    9,9'-((r,1-(Z,P),3-(Z,M))-2-fluoro-2,4,7-trimethyl-1H-indene-1,3(2H)-diylidene)bis(2-methoxy-9H-fluorene)

  • Compound C40H31FO2

    9,9'-((R,1-(E,P),3-(Z,M))-2-fluoro-2,4,7-trimethyl-1H-indene-1,3(2H)-diylidene)bis(2-methoxy-9H-fluorene)

  • Compound C40H31FO2

    9,9'-((S,1-(Z,P),3-(E,M))-2-fluoro-2,4,7-trimethyl-1H-indene-1,3(2H)-diylidene)bis(2-methoxy-9H-fluorene)

  • Compound C40H31FO2

    9,9'-((1-(Z,M),3-(Z,M))-2-fluoro-2,4,7-trimethyl-1H-indene-1,3(2H)-diylidene)bis(2-methoxy-9H-fluorene)

  • Compound C40H31FO2

    9,9'-((1-(E,P),3-(E,P))-2-fluoro-2,4,7-trimethyl-1H-indene-1,3(2H)-diylidene)bis(2-methoxy-9H-fluorene)

  • Compound C12H12O2

    2,4,7-trimethyl-1H-indene-1,3(2H)-dione

  • Compound C12H11FO2

    2-fluoro-2,4,7-trimethyl-1H-indene-1,3(2H)-dione

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Acknowledgements

This work was supported financially by the Netherlands Organization for Scientific Research (NWO-CW), The Royal Netherlands Academy of Arts and Sciences (KNAW), NanoNextNL of the Government of the Netherlands and 130 partners, the European Research Council (ERC; advanced grant no. 227897 to B.L.F.) and the Ministry of Education, Culture and Science (Gravitation programme no. 024.001.035). The authors thank P. van der Meulen for assistance with the NMR experiments, H.A.V. Kistemaker for pioneering synthesis and T.C. Pijper for discussions regarding DFT calculations.

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Affiliations

  1. Centre for Systems Chemistry, Stratingh Institute for Chemistry and Zernike Institute for Advanced Materials, Faculty of Mathematics and Natural Sciences, University of Groningen, Nijenborgh 4, Groningen 9747 AG, The Netherlands

    • Jos C. M. Kistemaker
    • , Peter Štacko
    • , Johan Visser
    •  & Ben L. Feringa

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Contributions

All authors contributed to various stages of the design and analysis of achiral motors. J.V. prepared the first meso motor. P.Š. performed the synthesis of advanced achiral motors. J.C.M.K. performed the computations and the experiments on photochemical and thermal behaviour. J.C.M.K. wrote the paper, with assistance from P.Š. and B.L.F.

Competing interests

The authors declare no competing financial interests.

Corresponding author

Correspondence to Ben L. Feringa.

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DOI

https://doi.org/10.1038/nchem.2362

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