Fine tuning of molecular rotor function in photochemical molecular switches

Matthijs K. J. ter Wiel; Ben L. Feringa

doi:10.1016/j.tet.2009.03.081

Fine tuning of molecular rotor function in photochemical molecular switches

Matthijs K. J. ter Wiel, Ben L. Feringa^*

^*Corresponding author for this work

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Abstract

Molecular switches are used as scaffolds for the construction of controlled molecular rotors. The internal position of the switching entity in the molecule controls the dynamic behaviour of the rotor moiety in the molecule. Six new molecular motors with o-xylyl rotor moieties were prepared on the basis of an overcrowded alkene, and their dynamics were systematically studied by 2D EXSY NMR, Variation of the (hetero-)atoms in the upper and lower halves of the overcrowded alkene allows fine tuning of the rate of rotation of the o-xylyl rotor in the lower half of the molecule. For all rotors it was observed that the rotation barrier for the trans-isomer was higher than that of the corresponding cis-isomer. The results are analyzed and discussed in terms of differences in steric interactions in the presented system. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4332-4339
Number of pages	8
Journal	Tetrahedron
Volume	65
Issue number	22
DOIs	https://doi.org/10.1016/j.tet.2009.03.081
Publication status	Published - 30-May-2009

Keywords

STERICALLY OVERCROWDED ALKENES
SINGLE STEREOGENIC CENTER
TWO-DIMENSIONAL NMR
UNIDIRECTIONAL ROTATION
2D NMR
DYNAMIC-BEHAVIOR
RATE CONSTANTS
MOTORS
SPECTROSCOPY
GYROSCOPES

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@article{09262588d7654a2f8b49fc5d220caa2b,

title = "Fine tuning of molecular rotor function in photochemical molecular switches",

abstract = "Molecular switches are used as scaffolds for the construction of controlled molecular rotors. The internal position of the switching entity in the molecule controls the dynamic behaviour of the rotor moiety in the molecule. Six new molecular motors with o-xylyl rotor moieties were prepared on the basis of an overcrowded alkene, and their dynamics were systematically studied by 2D EXSY NMR, Variation of the (hetero-)atoms in the upper and lower halves of the overcrowded alkene allows fine tuning of the rate of rotation of the o-xylyl rotor in the lower half of the molecule. For all rotors it was observed that the rotation barrier for the trans-isomer was higher than that of the corresponding cis-isomer. The results are analyzed and discussed in terms of differences in steric interactions in the presented system. (C) 2009 Elsevier Ltd. All rights reserved.",

keywords = "STERICALLY OVERCROWDED ALKENES, SINGLE STEREOGENIC CENTER, TWO-DIMENSIONAL NMR, UNIDIRECTIONAL ROTATION, 2D NMR, DYNAMIC-BEHAVIOR, RATE CONSTANTS, MOTORS, SPECTROSCOPY, GYROSCOPES",

author = "{ter Wiel}, {Matthijs K. J.} and Feringa, {Ben L.}",

year = "2009",

month = may,

day = "30",

doi = "10.1016/j.tet.2009.03.081",

language = "English",

volume = "65",

pages = "4332--4339",

journal = "Tetrahedron",

issn = "0040-4020",

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TY - JOUR

T1 - Fine tuning of molecular rotor function in photochemical molecular switches

AU - ter Wiel, Matthijs K. J.

AU - Feringa, Ben L.

PY - 2009/5/30

Y1 - 2009/5/30

N2 - Molecular switches are used as scaffolds for the construction of controlled molecular rotors. The internal position of the switching entity in the molecule controls the dynamic behaviour of the rotor moiety in the molecule. Six new molecular motors with o-xylyl rotor moieties were prepared on the basis of an overcrowded alkene, and their dynamics were systematically studied by 2D EXSY NMR, Variation of the (hetero-)atoms in the upper and lower halves of the overcrowded alkene allows fine tuning of the rate of rotation of the o-xylyl rotor in the lower half of the molecule. For all rotors it was observed that the rotation barrier for the trans-isomer was higher than that of the corresponding cis-isomer. The results are analyzed and discussed in terms of differences in steric interactions in the presented system. (C) 2009 Elsevier Ltd. All rights reserved.

AB - Molecular switches are used as scaffolds for the construction of controlled molecular rotors. The internal position of the switching entity in the molecule controls the dynamic behaviour of the rotor moiety in the molecule. Six new molecular motors with o-xylyl rotor moieties were prepared on the basis of an overcrowded alkene, and their dynamics were systematically studied by 2D EXSY NMR, Variation of the (hetero-)atoms in the upper and lower halves of the overcrowded alkene allows fine tuning of the rate of rotation of the o-xylyl rotor in the lower half of the molecule. For all rotors it was observed that the rotation barrier for the trans-isomer was higher than that of the corresponding cis-isomer. The results are analyzed and discussed in terms of differences in steric interactions in the presented system. (C) 2009 Elsevier Ltd. All rights reserved.

KW - STERICALLY OVERCROWDED ALKENES

KW - SINGLE STEREOGENIC CENTER

KW - TWO-DIMENSIONAL NMR

KW - UNIDIRECTIONAL ROTATION

KW - 2D NMR

KW - DYNAMIC-BEHAVIOR

KW - RATE CONSTANTS

KW - MOTORS

KW - SPECTROSCOPY

KW - GYROSCOPES

U2 - 10.1016/j.tet.2009.03.081

DO - 10.1016/j.tet.2009.03.081

M3 - Article

SN - 0040-4020

VL - 65

SP - 4332

EP - 4339

JO - Tetrahedron

JF - Tetrahedron

IS - 22

ER -

Fine tuning of molecular rotor function in photochemical molecular switches

Abstract

Keywords

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