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 for this work

Department of Chemistry

11 Citations (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.

Original language	English
Journal	Angewandte Chemie International Edition
Volume	58
Issue number	51
Pages (from-to)	18419-18423
ISSN	1433-7851
DOIs	https://doi.org/10.1002/anie.201910214
Publication status	Published - 16 Dec 2019

Access to Document

10.1002/anie.201910214

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

Cite this

@article{2f8f31b1d7414937bfa4f752cb38d9f6,

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

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.",

author = "Pedersen, {Stephan K.} and Kristina Eriksen and Michael Pittelkow",

year = "2019",

month = dec,

day = "16",

doi = "10.1002/anie.201910214",

language = "English",

volume = "58",

pages = "18419--18423",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "Wiley-VCH Verlag GmbH & Co. KGaA",

number = "51",

}

TY - JOUR

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

Access to Document

Fingerprint

Cite this