Visible-Light-Driven Tunable Molecular Motors Based on Oxindole

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2019 Apr 25

PMID 31017421

Citations 27

Authors

Diederik Roke

Metin Sen

Wojciech Danowski

Sander J Wezenberg

Ben L Feringa

Affiliations

Soon will be listed here.

Abstract

Molecular rotary motors based on oxindole which can be driven by visible light are presented. This novel class of motors can be easily synthesized via a Knoevenagel condensation, and the choice of different upper halves allows for the facile tuning of their rotational speed. The four-step rotational cycle was explored using DFT calculations, and the expected photochemical and thermal isomerization behavior was confirmed by NMR, UV/vis, and CD spectroscopy. These oxindole motors offer attractive prospects for functional materials responsive to light.

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References

Koumura N, Zijlstra R, Van Delden R, Harada N, Feringa B . Light-driven monodirectional molecular rotor. Nature. 1999; 401(6749):152-5. DOI: 10.1038/43646. View

Balzani V , Credi , Raymo , Stoddart . Artificial Molecular Machines. Angew Chem Int Ed Engl. 2000; 39(19):3348-3391. DOI: 10.1002/1521-3773(20001002)39:19<3348::aid-anie3348>3.0.co;2-x. View

Koumura N, Geertsema E, van Gelder M, Meetsma A, Feringa B . Second generation light-driven molecular motors. Unidirectional rotation controlled by a single stereogenic center with near-perfect photoequilibria and acceleration of the speed of rotation by structural modification. J Am Chem Soc. 2002; 124(18):5037-51. DOI: 10.1021/ja012499i. View

van Delden R, Koumura N, Schoevaars A, Meetsma A, Feringa B . A donor-acceptor substituted molecular motor: unidirectional rotation driven by visible light. Org Biomol Chem. 2003; 1(1):33-5. DOI: 10.1039/b209378b. View

Kinbara K, Aida T . Toward intelligent molecular machines: directed motions of biological and artificial molecules and assemblies. Chem Rev. 2005; 105(4):1377-400. DOI: 10.1021/cr030071r. View

Vicario J, Meetsma A, Feringa B . Controlling the speed of rotation in molecular motors. Dramatic acceleration of the rotary motion by structural modification. Chem Commun (Camb). 2005; (47):5910-2. DOI: 10.1039/b507264f. View

Eelkema R, Pollard M, Vicario J, Katsonis N, Serrano Ramon B, Bastiaansen C . Molecular machines: nanomotor rotates microscale objects. Nature. 2006; 440(7081):163. DOI: 10.1038/440163a. View

Pollard M, Meetsma A, Feringa B . A redesign of light-driven rotary molecular motors. Org Biomol Chem. 2008; 6(3):507-12. DOI: 10.1039/b715652a. View

Klok M, Boyle N, Pryce M, Meetsma A, Browne W, Feringa B . MHz unidirectional rotation of molecular rotary motors. J Am Chem Soc. 2008; 130(32):10484-5. DOI: 10.1021/ja8037245. View

10.

Browne W, Feringa B . Making molecular machines work. Nat Nanotechnol. 2008; 1(1):25-35. DOI: 10.1038/nnano.2006.45. View

11.

Wang J, Feringa B . Dynamic control of chiral space in a catalytic asymmetric reaction using a molecular motor. Science. 2011; 331(6023):1429-32. DOI: 10.1126/science.1199844. View

12.

Cnossen A, Hou L, Pollard M, Wesenhagen P, Browne W, Feringa B . Driving unidirectional molecular rotary motors with visible light by intra- and intermolecular energy transfer from palladium porphyrin. J Am Chem Soc. 2012; 134(42):17613-9. DOI: 10.1021/ja306986g. View

13.

Cnossen A, Kistemaker J, Kojima T, Feringa B . Structural dynamics of overcrowded alkene-based molecular motors during thermal isomerization. J Org Chem. 2014; 79(3):927-35. DOI: 10.1021/jo402301j. View

14.

Chen K, Ivashenko O, Carroll G, Robertus J, Kistemaker J, London G . Control of surface wettability using tripodal light-activated molecular motors. J Am Chem Soc. 2014; 136(8):3219-24. DOI: 10.1021/ja412110t. View

15.

Greb L, Lehn J . Light-driven molecular motors: imines as four-step or two-step unidirectional rotors. J Am Chem Soc. 2014; 136(38):13114-7. DOI: 10.1021/ja506034n. View

16.

Li Q, Fuks G, Moulin E, Maaloum M, Rawiso M, Kulic I . Macroscopic contraction of a gel induced by the integrated motion of light-driven molecular motors. Nat Nanotechnol. 2015; 10(2):161-5. DOI: 10.1038/nnano.2014.315. View

17.

Bleger D, Hecht S . Visible-Light-Activated Molecular Switches. Angew Chem Int Ed Engl. 2015; 54(39):11338-49. DOI: 10.1002/anie.201500628. View

18.

Kay E, Leigh D . Rise of the Molecular Machines. Angew Chem Int Ed Engl. 2015; 54(35):10080-8. PMC: 4557038. DOI: 10.1002/anie.201503375. View

19.

Wezenberg S, Chen K, Feringa B . Visible-Light-Driven Photoisomerization and Increased Rotation Speed of a Molecular Motor Acting as a Ligand in a Ruthenium(II) Complex. Angew Chem Int Ed Engl. 2015; 54(39):11457-61. DOI: 10.1002/anie.201505781. View

20.

Guentner M, Schildhauer M, Thumser S, Mayer P, Stephenson D, Mayer P . Sunlight-powered kHz rotation of a hemithioindigo-based molecular motor. Nat Commun. 2015; 6:8406. PMC: 4598625. DOI: 10.1038/ncomms9406. View