Fluorescence switching with subphthalocyanine-dihydroazulene dyads

Henrik Gotfredsen; Martin Drøhse Kilde; Marco Santella; Anders Kadziola; Mogens Brøndsted Nielsen

doi:10.1039/c8me00075a

Fluorescence switching with subphthalocyanine-dihydroazulene dyads

Henrik Gotfredsen, Martin Drøhse Kilde, Marco Santella, Anders Kadziola, Mogens Brøndsted Nielsen

Kemisk Institut

6 Citationer (Scopus)

Abstract

One convenient way of reversibly modulating the emission properties of a fluorophore is by introducing a photochromic unit that upon irradiation is converted into an isomeric unit that can quench the fluorescence of the fluorophore. Here we present the synthesis of two dyads containing a boron subphthalocyanine (SubPc) fluorophore and the dihydroazulene (DHA) photoswitch. Upon photoisomerization, the DHA unit is converted to a vinylheptafulvene (VHF) unit that was found to efficiently quench the SubPc fluorescence when placed at the axial boron position of the SubPc. The original fluorescence was restored by thermal conversion of the VHF to DHA. Fluorescence was thereby turned off and on by successive light-heat cycles. The other dyad has the DHA unit placed at the periphery of the SubPc, and this dyad showed instead limited photostability.

Originalsprog	Engelsk
Tidsskrift	Molecular Systems Design and Engineering
Vol/bind	4
Udgave nummer	1
Sider (fra-til)	199-205
ISSN	2058-9689
DOI	https://doi.org/10.1039/c8me00075a
Status	Udgivet - feb. 2019

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10.1039/c8me00075a

Citationsformater

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title = "Fluorescence switching with subphthalocyanine-dihydroazulene dyads",

abstract = "One convenient way of reversibly modulating the emission properties of a fluorophore is by introducing a photochromic unit that upon irradiation is converted into an isomeric unit that can quench the fluorescence of the fluorophore. Here we present the synthesis of two dyads containing a boron subphthalocyanine (SubPc) fluorophore and the dihydroazulene (DHA) photoswitch. Upon photoisomerization, the DHA unit is converted to a vinylheptafulvene (VHF) unit that was found to efficiently quench the SubPc fluorescence when placed at the axial boron position of the SubPc. The original fluorescence was restored by thermal conversion of the VHF to DHA. Fluorescence was thereby turned off and on by successive light-heat cycles. The other dyad has the DHA unit placed at the periphery of the SubPc, and this dyad showed instead limited photostability.",

author = "Henrik Gotfredsen and Kilde, {Martin Dr{\o}hse} and Marco Santella and Anders Kadziola and Nielsen, {Mogens Br{\o}ndsted}",

year = "2019",

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doi = "10.1039/c8me00075a",

language = "English",

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T1 - Fluorescence switching with subphthalocyanine-dihydroazulene dyads

AU - Gotfredsen, Henrik

AU - Kilde, Martin Drøhse

AU - Santella, Marco

AU - Kadziola, Anders

AU - Nielsen, Mogens Brøndsted

PY - 2019/2

Y1 - 2019/2

N2 - One convenient way of reversibly modulating the emission properties of a fluorophore is by introducing a photochromic unit that upon irradiation is converted into an isomeric unit that can quench the fluorescence of the fluorophore. Here we present the synthesis of two dyads containing a boron subphthalocyanine (SubPc) fluorophore and the dihydroazulene (DHA) photoswitch. Upon photoisomerization, the DHA unit is converted to a vinylheptafulvene (VHF) unit that was found to efficiently quench the SubPc fluorescence when placed at the axial boron position of the SubPc. The original fluorescence was restored by thermal conversion of the VHF to DHA. Fluorescence was thereby turned off and on by successive light-heat cycles. The other dyad has the DHA unit placed at the periphery of the SubPc, and this dyad showed instead limited photostability.

AB - One convenient way of reversibly modulating the emission properties of a fluorophore is by introducing a photochromic unit that upon irradiation is converted into an isomeric unit that can quench the fluorescence of the fluorophore. Here we present the synthesis of two dyads containing a boron subphthalocyanine (SubPc) fluorophore and the dihydroazulene (DHA) photoswitch. Upon photoisomerization, the DHA unit is converted to a vinylheptafulvene (VHF) unit that was found to efficiently quench the SubPc fluorescence when placed at the axial boron position of the SubPc. The original fluorescence was restored by thermal conversion of the VHF to DHA. Fluorescence was thereby turned off and on by successive light-heat cycles. The other dyad has the DHA unit placed at the periphery of the SubPc, and this dyad showed instead limited photostability.

U2 - 10.1039/c8me00075a

DO - 10.1039/c8me00075a

M3 - Journal article

SN - 2058-9689

VL - 4

SP - 199

EP - 205

JO - Molecular Systems Design and Engineering

JF - Molecular Systems Design and Engineering

IS - 1

ER -

Fluorescence switching with subphthalocyanine-dihydroazulene dyads

Abstract

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