Stabilizing Indigo Z-isomer via Intramolecular Associations of Redox-Active Appendages

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Standard

Stabilizing Indigo Z-isomer via Intramolecular Associations of Redox-Active Appendages. / Broløs, Line; Klaue, Kristin; Bendix, Jesper; Grubert, Lutz; Hecht, Stefan; Nielsen, Mogens Brøndsted.

I: European Journal of Organic Chemistry, Bind 2021, Nr. 46, 02.09.2021, s. 6304-6311.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Broløs, L, Klaue, K, Bendix, J, Grubert, L, Hecht, S & Nielsen, MB 2021, 'Stabilizing Indigo Z-isomer via Intramolecular Associations of Redox-Active Appendages', European Journal of Organic Chemistry, bind 2021, nr. 46, s. 6304-6311. https://doi.org/10.1002/ejoc.202100781

APA

Broløs, L., Klaue, K., Bendix, J., Grubert, L., Hecht, S., & Nielsen, M. B. (2021). Stabilizing Indigo Z-isomer via Intramolecular Associations of Redox-Active Appendages. European Journal of Organic Chemistry, 2021(46), 6304-6311. https://doi.org/10.1002/ejoc.202100781

Vancouver

Broløs L, Klaue K, Bendix J, Grubert L, Hecht S, Nielsen MB. Stabilizing Indigo Z-isomer via Intramolecular Associations of Redox-Active Appendages. European Journal of Organic Chemistry. 2021 sep. 2;2021(46):6304-6311. https://doi.org/10.1002/ejoc.202100781

Author

Broløs, Line ; Klaue, Kristin ; Bendix, Jesper ; Grubert, Lutz ; Hecht, Stefan ; Nielsen, Mogens Brøndsted. / Stabilizing Indigo Z-isomer via Intramolecular Associations of Redox-Active Appendages. I: European Journal of Organic Chemistry. 2021 ; Bind 2021, Nr. 46. s. 6304-6311.

Bibtex

@article{57fb81ead6de4d4d896c245ad41cc528,
title = "Stabilizing Indigo Z-isomer via Intramolecular Associations of Redox-Active Appendages",
abstract = "Photoswitchable small molecules, such as N , N'- disubstituted indigos, have received great interest within fields such as pharmacology, energy storage, and functional materials, as they represent key building blocks for reversible and non-invasive control of chemical processes. However, to ensure applicability of photochromic systems it is of paramount importance to manipulate the photostationary state. In this work, we achieved this by tethering two redox-active indenofluorene-extended tetrathiafulvalene units to an N , N' -disubstituted indigo photoswitch. Upon two-electron oxidation, we observe significantly enhanced stability of the Z -isomer, compared to the neutral compound, illustrated by a substantial increase in the half-life from 0.48 seconds to 22 hours. This remarkable stabilization is ascribed to formation of strong, intramolecular pi-dimers between the oxidized subunits.",
keywords = "Cross-coupling, Fused-ring systems, Photochromism, sulfur heterocycles, Supramolecular chemistry, Cross-coupling, Fused-ring systems, Photochromism, sulfur heterocycles, Supramolecular chemistry",
author = "Line Brol{\o}s and Kristin Klaue and Jesper Bendix and Lutz Grubert and Stefan Hecht and Nielsen, {Mogens Br{\o}ndsted}",
year = "2021",
month = sep,
day = "2",
doi = "10.1002/ejoc.202100781",
language = "English",
volume = "2021",
pages = "6304--6311",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "46",

}

RIS

TY - JOUR

T1 - Stabilizing Indigo Z-isomer via Intramolecular Associations of Redox-Active Appendages

AU - Broløs, Line

AU - Klaue, Kristin

AU - Bendix, Jesper

AU - Grubert, Lutz

AU - Hecht, Stefan

AU - Nielsen, Mogens Brøndsted

PY - 2021/9/2

Y1 - 2021/9/2

N2 - Photoswitchable small molecules, such as N , N'- disubstituted indigos, have received great interest within fields such as pharmacology, energy storage, and functional materials, as they represent key building blocks for reversible and non-invasive control of chemical processes. However, to ensure applicability of photochromic systems it is of paramount importance to manipulate the photostationary state. In this work, we achieved this by tethering two redox-active indenofluorene-extended tetrathiafulvalene units to an N , N' -disubstituted indigo photoswitch. Upon two-electron oxidation, we observe significantly enhanced stability of the Z -isomer, compared to the neutral compound, illustrated by a substantial increase in the half-life from 0.48 seconds to 22 hours. This remarkable stabilization is ascribed to formation of strong, intramolecular pi-dimers between the oxidized subunits.

AB - Photoswitchable small molecules, such as N , N'- disubstituted indigos, have received great interest within fields such as pharmacology, energy storage, and functional materials, as they represent key building blocks for reversible and non-invasive control of chemical processes. However, to ensure applicability of photochromic systems it is of paramount importance to manipulate the photostationary state. In this work, we achieved this by tethering two redox-active indenofluorene-extended tetrathiafulvalene units to an N , N' -disubstituted indigo photoswitch. Upon two-electron oxidation, we observe significantly enhanced stability of the Z -isomer, compared to the neutral compound, illustrated by a substantial increase in the half-life from 0.48 seconds to 22 hours. This remarkable stabilization is ascribed to formation of strong, intramolecular pi-dimers between the oxidized subunits.

KW - Cross-coupling

KW - Fused-ring systems

KW - Photochromism

KW - sulfur heterocycles

KW - Supramolecular chemistry

KW - Cross-coupling

KW - Fused-ring systems

KW - Photochromism

KW - sulfur heterocycles

KW - Supramolecular chemistry

U2 - 10.1002/ejoc.202100781

DO - 10.1002/ejoc.202100781

M3 - Journal article

VL - 2021

SP - 6304

EP - 6311

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 46

ER -

ID: 279650655