Asymmetric Synthesis of Second-Generation Light-Driven Molecular Motors

Thomas van Leeuwen; Wojciech Danowski; Edwin Otten; Sander J Wezenberg; Ben L Feringa

doi:10.1021/acs.joc.7b00852

Asymmetric Synthesis of Second-Generation Light-Driven Molecular Motors

Thomas van Leeuwen, Wojciech Danowski, Edwin Otten, Sander J Wezenberg, Ben L Feringa

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Abstract

The enantiomeric homogeneity of light-driven molecular motors based on overcrowded alkenes is crucial in their application as either unidirectional rotors or as chiral multistate switches. It was challenging to obtain these compounds as single enantiomers via the established synthetic procedures due to loss of optical purity in the key step, i.e., the Barton-Kellogg olefination reaction. Searching for strategies to avoid racemization, a new class of light-driven molecular motors was designed, synthesized, and studied. The stereochemical integrity was fully preserved throughout the synthesis, and on the basis of photochemical and kinetic studies using UV/vis, CD, and (1)H NMR spectroscopy, it was established that they still function properly as unidirectional molecular motors.

Original language	English
Pages (from-to)	5027-5033
Number of pages	7
Journal	The Journal of Organic Chemistry
Volume	82
Issue number	10
DOIs	https://doi.org/10.1021/acs.joc.7b00852
Publication status	Published - 2017

Keywords

TETRASUBSTITUTED HELICAL ALKENES
CARBOPALLADATION/C-H-ACTIVATION
OVERCROWDED ALKENES
MACHINES
SWITCHES
DENSITY

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CCDC 1551211: Experimental Crystal Structure Determination
Leeuwen ,van, T. (Contributor), Danowski, W. (Contributor), Otten, E. (Contributor), Wezenberg, S. J. (Contributor) & Feringa, B. L. (Contributor), University of Groningen, 19-May-2017
DOI: 10.5517/ccdc.csd.cc1p2520
Dataset

Cite this

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title = "Asymmetric Synthesis of Second-Generation Light-Driven Molecular Motors",

abstract = "The enantiomeric homogeneity of light-driven molecular motors based on overcrowded alkenes is crucial in their application as either unidirectional rotors or as chiral multistate switches. It was challenging to obtain these compounds as single enantiomers via the established synthetic procedures due to loss of optical purity in the key step, i.e., the Barton-Kellogg olefination reaction. Searching for strategies to avoid racemization, a new class of light-driven molecular motors was designed, synthesized, and studied. The stereochemical integrity was fully preserved throughout the synthesis, and on the basis of photochemical and kinetic studies using UV/vis, CD, and (1)H NMR spectroscopy, it was established that they still function properly as unidirectional molecular motors.",

keywords = "TETRASUBSTITUTED HELICAL ALKENES, CARBOPALLADATION/C-H-ACTIVATION, OVERCROWDED ALKENES, MACHINES, SWITCHES, DENSITY",

author = "\{van Leeuwen\}, Thomas and Wojciech Danowski and Edwin Otten and Wezenberg, \{Sander J\} and Feringa, \{Ben L\}",

year = "2017",

doi = "10.1021/acs.joc.7b00852",

language = "English",

volume = "82",

pages = "5027--5033",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "AMER CHEMICAL SOC INC",

number = "10",

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TY - JOUR

T1 - Asymmetric Synthesis of Second-Generation Light-Driven Molecular Motors

AU - van Leeuwen, Thomas

AU - Danowski, Wojciech

AU - Otten, Edwin

AU - Wezenberg, Sander J

AU - Feringa, Ben L

PY - 2017

Y1 - 2017

N2 - The enantiomeric homogeneity of light-driven molecular motors based on overcrowded alkenes is crucial in their application as either unidirectional rotors or as chiral multistate switches. It was challenging to obtain these compounds as single enantiomers via the established synthetic procedures due to loss of optical purity in the key step, i.e., the Barton-Kellogg olefination reaction. Searching for strategies to avoid racemization, a new class of light-driven molecular motors was designed, synthesized, and studied. The stereochemical integrity was fully preserved throughout the synthesis, and on the basis of photochemical and kinetic studies using UV/vis, CD, and (1)H NMR spectroscopy, it was established that they still function properly as unidirectional molecular motors.

AB - The enantiomeric homogeneity of light-driven molecular motors based on overcrowded alkenes is crucial in their application as either unidirectional rotors or as chiral multistate switches. It was challenging to obtain these compounds as single enantiomers via the established synthetic procedures due to loss of optical purity in the key step, i.e., the Barton-Kellogg olefination reaction. Searching for strategies to avoid racemization, a new class of light-driven molecular motors was designed, synthesized, and studied. The stereochemical integrity was fully preserved throughout the synthesis, and on the basis of photochemical and kinetic studies using UV/vis, CD, and (1)H NMR spectroscopy, it was established that they still function properly as unidirectional molecular motors.

KW - TETRASUBSTITUTED HELICAL ALKENES

KW - CARBOPALLADATION/C-H-ACTIVATION

KW - OVERCROWDED ALKENES

KW - MACHINES

KW - SWITCHES

KW - DENSITY

U2 - 10.1021/acs.joc.7b00852

DO - 10.1021/acs.joc.7b00852

M3 - Article

C2 - 28459576

SN - 0022-3263

VL - 82

SP - 5027

EP - 5033

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 10

ER -

Asymmetric Synthesis of Second-Generation Light-Driven Molecular Motors

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Keywords

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Datasets

CCDC 1551211: Experimental Crystal Structure Determination

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