Symmetric, Unsymmetrical, and Asymmetric [7]-, [10]-, and [13]Helicenes

Stephan K. Pedersen; Kristina Eriksen; Michael Pittelkow

doi:10.1002/anie.201910214

Symmetric, Unsymmetrical, and Asymmetric [7]-, [10]-, and [13]Helicenes

Stephan K. Pedersen, Kristina Eriksen, Michael Pittelkow^*

^*Corresponding author af dette arbejde

Kemisk Institut

11 Citationer (Scopus)

Abstract

Fully aromatic helicenes with more than one pitch-length are illustrious synthetic targets with potential applications in advanced optical devices and nano-electronics. The task of extending the length of fully conjugated helicenes past one pitch length is challenging. Now, the synthesis of a series of azaoxa[7]-, [10]-, and [13]helicenes is described. The synthesis is based on iterative oxidative furan formation between 3,6-dihydroxycarbazoles and/or 2-naphthols. The flexibility of the presented method allows the convenient and scalable synthesis of symmetric, unsymmetrical, and asymmetric homo-chiral structures. The [13]helicenes can be synthetically functionalized both at the termini and the periphery. The full range of helicenes were characterized using NMR and optical spectroscopy (UV/Vis, fluorescence, and CD) along with single-crystal X-ray crystallography. The enantiomers of the [13]helicenes are the longest optically pure helicenes isolated to date.

Originalsprog	Engelsk
Tidsskrift	Angewandte Chemie International Edition
Vol/bind	58
Udgave nummer	51
Sider (fra-til)	18419-18423
ISSN	1433-7851
DOI	https://doi.org/10.1002/anie.201910214
Status	Udgivet - 16 dec. 2019

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10.1002/anie.201910214

http://doi.wiley.com/10.1002/anie.201910214

Citationsformater

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abstract = "Fully aromatic helicenes with more than one pitch-length are illustrious synthetic targets with potential applications in advanced optical devices and nano-electronics. The task of extending the length of fully conjugated helicenes past one pitch length is challenging. Now, the synthesis of a series of azaoxa[7]-, [10]-, and [13]helicenes is described. The synthesis is based on iterative oxidative furan formation between 3,6-dihydroxycarbazoles and/or 2-naphthols. The flexibility of the presented method allows the convenient and scalable synthesis of symmetric, unsymmetrical, and asymmetric homo-chiral structures. The [13]helicenes can be synthetically functionalized both at the termini and the periphery. The full range of helicenes were characterized using NMR and optical spectroscopy (UV/Vis, fluorescence, and CD) along with single-crystal X-ray crystallography. The enantiomers of the [13]helicenes are the longest optically pure helicenes isolated to date.",

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T1 - Symmetric, Unsymmetrical, and Asymmetric [7]-, [10]-, and [13]Helicenes

AU - Pedersen, Stephan K.

AU - Eriksen, Kristina

AU - Pittelkow, Michael

PY - 2019/12/16

Y1 - 2019/12/16

N2 - Fully aromatic helicenes with more than one pitch-length are illustrious synthetic targets with potential applications in advanced optical devices and nano-electronics. The task of extending the length of fully conjugated helicenes past one pitch length is challenging. Now, the synthesis of a series of azaoxa[7]-, [10]-, and [13]helicenes is described. The synthesis is based on iterative oxidative furan formation between 3,6-dihydroxycarbazoles and/or 2-naphthols. The flexibility of the presented method allows the convenient and scalable synthesis of symmetric, unsymmetrical, and asymmetric homo-chiral structures. The [13]helicenes can be synthetically functionalized both at the termini and the periphery. The full range of helicenes were characterized using NMR and optical spectroscopy (UV/Vis, fluorescence, and CD) along with single-crystal X-ray crystallography. The enantiomers of the [13]helicenes are the longest optically pure helicenes isolated to date.

AB - Fully aromatic helicenes with more than one pitch-length are illustrious synthetic targets with potential applications in advanced optical devices and nano-electronics. The task of extending the length of fully conjugated helicenes past one pitch length is challenging. Now, the synthesis of a series of azaoxa[7]-, [10]-, and [13]helicenes is described. The synthesis is based on iterative oxidative furan formation between 3,6-dihydroxycarbazoles and/or 2-naphthols. The flexibility of the presented method allows the convenient and scalable synthesis of symmetric, unsymmetrical, and asymmetric homo-chiral structures. The [13]helicenes can be synthetically functionalized both at the termini and the periphery. The full range of helicenes were characterized using NMR and optical spectroscopy (UV/Vis, fluorescence, and CD) along with single-crystal X-ray crystallography. The enantiomers of the [13]helicenes are the longest optically pure helicenes isolated to date.

U2 - 10.1002/anie.201910214

DO - 10.1002/anie.201910214

M3 - Journal article

C2 - 31609048

SN - 1433-7851

VL - 58

SP - 18419

EP - 18423

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 51

ER -

Symmetric, Unsymmetrical, and Asymmetric [7]-, [10]-, and [13]Helicenes

Abstract

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