Regioselective Transformation of Long π-Conjugated Backbones: From Oligofurans to Oligoarenes

Sunita Gadakh; Linda J.W. Shimon; Ori Gidron

doi:10.1002/anie.201705914

Regioselective Transformation of Long π-Conjugated Backbones: From Oligofurans to Oligoarenes

Sunita Gadakh, Linda J.W. Shimon, Ori Gidron^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

We demonstrate the transformation of oligofurans through sequential Diels–Alder cycloaddition reactions to provide oligoarenes in two chemical steps, regardless of the oligomer length. By this method, oligonaphthalenes containing up to six units were obtained in high yield through the formation of up to 12 new C−C bonds. The versatility of this method was demonstrated for various polyaromatic hydrocarbons. The regioselectivity of this process enabled the synthesis of a library of substituted triarylenes from a single terfuran precursor by modification of the dienophile strength and the order of addition. Overall, this study demonstrates that long oligofurans are interesting not only as organic electronic materials, but also as starting materials for the formation of various conjugated systems.

Original language	American English
Pages (from-to)	13601-13605
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	44
DOIs	https://doi.org/10.1002/anie.201705914
State	Published - 23 Oct 2017

Bibliographical note

Funding Information:
This research was supported by the Israel Science Foundation (grant No. 1789/16). We are grateful to Dr. Ilit Cohen from the Research Support Unit, Weizmann Institute of Science for the FD-MS measurements.

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Diels–Alder cycloaddition
oligoarenes
oligofurans
organic electronic materials
π conjugation

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10.1002/anie.201705914

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title = "Regioselective Transformation of Long π-Conjugated Backbones: From Oligofurans to Oligoarenes",

abstract = "We demonstrate the transformation of oligofurans through sequential Diels–Alder cycloaddition reactions to provide oligoarenes in two chemical steps, regardless of the oligomer length. By this method, oligonaphthalenes containing up to six units were obtained in high yield through the formation of up to 12 new C−C bonds. The versatility of this method was demonstrated for various polyaromatic hydrocarbons. The regioselectivity of this process enabled the synthesis of a library of substituted triarylenes from a single terfuran precursor by modification of the dienophile strength and the order of addition. Overall, this study demonstrates that long oligofurans are interesting not only as organic electronic materials, but also as starting materials for the formation of various conjugated systems.",

keywords = "Diels–Alder cycloaddition, oligoarenes, oligofurans, organic electronic materials, π conjugation",

author = "Sunita Gadakh and Shimon, {Linda J.W.} and Ori Gidron",

note = "Funding Information: This research was supported by the Israel Science Foundation (grant No. 1789/16). We are grateful to Dr. Ilit Cohen from the Research Support Unit, Weizmann Institute of Science for the FD-MS measurements. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Shimon, Linda J.W.

AU - Gidron, Ori

N1 - Funding Information: This research was supported by the Israel Science Foundation (grant No. 1789/16). We are grateful to Dr. Ilit Cohen from the Research Support Unit, Weizmann Institute of Science for the FD-MS measurements. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/10/23

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N2 - We demonstrate the transformation of oligofurans through sequential Diels–Alder cycloaddition reactions to provide oligoarenes in two chemical steps, regardless of the oligomer length. By this method, oligonaphthalenes containing up to six units were obtained in high yield through the formation of up to 12 new C−C bonds. The versatility of this method was demonstrated for various polyaromatic hydrocarbons. The regioselectivity of this process enabled the synthesis of a library of substituted triarylenes from a single terfuran precursor by modification of the dienophile strength and the order of addition. Overall, this study demonstrates that long oligofurans are interesting not only as organic electronic materials, but also as starting materials for the formation of various conjugated systems.

AB - We demonstrate the transformation of oligofurans through sequential Diels–Alder cycloaddition reactions to provide oligoarenes in two chemical steps, regardless of the oligomer length. By this method, oligonaphthalenes containing up to six units were obtained in high yield through the formation of up to 12 new C−C bonds. The versatility of this method was demonstrated for various polyaromatic hydrocarbons. The regioselectivity of this process enabled the synthesis of a library of substituted triarylenes from a single terfuran precursor by modification of the dienophile strength and the order of addition. Overall, this study demonstrates that long oligofurans are interesting not only as organic electronic materials, but also as starting materials for the formation of various conjugated systems.

KW - Diels–Alder cycloaddition

KW - oligoarenes

KW - oligofurans

KW - organic electronic materials

KW - π conjugation

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DO - 10.1002/anie.201705914

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AN - SCOPUS:85030474129

SN - 1433-7851

VL - 56

SP - 13601

EP - 13605

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 44

ER -

Regioselective Transformation of Long π-Conjugated Backbones: From Oligofurans to Oligoarenes

Abstract

Bibliographical note

Keywords

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