Dihydroazulene-Boron Subphthalocyanine Conjugates with Oligo(phenyleneethynylene) Bridging Unit: Photoswitchable Fluorophores

Esmeralda Bukuroshi; Anne Ugleholdt Petersen; Cecilie Jensen; Mathias Kirkholt Lund; Martin Kühnel; Kasper Nørgaard; Timothy P. Bender; Mogens Brøndsted Nielsen

doi:10.1002/ejoc.202300284

Dihydroazulene-Boron Subphthalocyanine Conjugates with Oligo(phenyleneethynylene) Bridging Unit: Photoswitchable Fluorophores

Esmeralda Bukuroshi, Anne Ugleholdt Petersen, Cecilie Jensen, Mathias Kirkholt Lund, Martin Kühnel, Kasper Nørgaard, Timothy P. Bender^*, Mogens Brøndsted Nielsen

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

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Abstract

In this work, we have linked the dihydroazulene (DHA)/vinylheptafulvene (VHF) photo-/thermoswitch and the boron subphthalocyanine (BsubPc) fluorophore via an axial oligo(phenyleneethynylene) bridging unit into new DHA-BsubPc conjugates. The objectives were to elucidate the influence of BsubPc on the DHA/VHF switching reactions and the influence of DHA/VHF on the BsubPc fluorescence in these conjugates for which the entire axial substituent connected to boron comprises one large, conjugated scaffold. We present the synthesis and properties of DHA-BsubPc conjugates with varying peripheral substituents on the BsubPc core, being either unsubstituted (H₁₂BsubPc) or partially fluorinated (F₆BsubPc). Fluorination of the BsubPc core provided a remarkable increase in the reversibility of the DHA-VHF interconversions promoted by light and heat, respectively, and accompanied by on/off switching of the BsubPc fluorescence. Synthetically, the units were connected using Sonogashira coupling reactions of suitable acetylenic building blocks.

Original language	English
Article number	e202300284
Journal	European Journal of Organic Chemistry
Volume	26
Issue number	24
Number of pages	9
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.202300284
Publication status	Published - 2023

Bibliographical note

Publisher Copyright:
© 2023 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.

Keywords

chromophores
cross-coupling
fluorescence
molecular electronics
photochromism

Access to Document

10.1002/ejoc.202300284

FulltextFinal published version, 5.6 MBLicence: CC BY

Cite this

Bukuroshi, E., Ugleholdt Petersen, A., Jensen, C., Kirkholt Lund, M., Kühnel, M., Nørgaard, K., Bender, T. P., & Brøndsted Nielsen, M. (2023). Dihydroazulene-Boron Subphthalocyanine Conjugates with Oligo(phenyleneethynylene) Bridging Unit: Photoswitchable Fluorophores. European Journal of Organic Chemistry, 26(24), Article e202300284. https://doi.org/10.1002/ejoc.202300284

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abstract = "In this work, we have linked the dihydroazulene (DHA)/vinylheptafulvene (VHF) photo-/thermoswitch and the boron subphthalocyanine (BsubPc) fluorophore via an axial oligo(phenyleneethynylene) bridging unit into new DHA-BsubPc conjugates. The objectives were to elucidate the influence of BsubPc on the DHA/VHF switching reactions and the influence of DHA/VHF on the BsubPc fluorescence in these conjugates for which the entire axial substituent connected to boron comprises one large, conjugated scaffold. We present the synthesis and properties of DHA-BsubPc conjugates with varying peripheral substituents on the BsubPc core, being either unsubstituted (H12BsubPc) or partially fluorinated (F6BsubPc). Fluorination of the BsubPc core provided a remarkable increase in the reversibility of the DHA-VHF interconversions promoted by light and heat, respectively, and accompanied by on/off switching of the BsubPc fluorescence. Synthetically, the units were connected using Sonogashira coupling reactions of suitable acetylenic building blocks.",

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author = "Esmeralda Bukuroshi and {Ugleholdt Petersen}, Anne and Cecilie Jensen and {Kirkholt Lund}, Mathias and Martin K{\"u}hnel and Kasper N{\o}rgaard and Bender, {Timothy P.} and {Br{\o}ndsted Nielsen}, Mogens",

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T2 - Photoswitchable Fluorophores

AU - Bukuroshi, Esmeralda

AU - Ugleholdt Petersen, Anne

AU - Jensen, Cecilie

AU - Kirkholt Lund, Mathias

AU - Kühnel, Martin

AU - Nørgaard, Kasper

AU - Bender, Timothy P.

AU - Brøndsted Nielsen, Mogens

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N2 - In this work, we have linked the dihydroazulene (DHA)/vinylheptafulvene (VHF) photo-/thermoswitch and the boron subphthalocyanine (BsubPc) fluorophore via an axial oligo(phenyleneethynylene) bridging unit into new DHA-BsubPc conjugates. The objectives were to elucidate the influence of BsubPc on the DHA/VHF switching reactions and the influence of DHA/VHF on the BsubPc fluorescence in these conjugates for which the entire axial substituent connected to boron comprises one large, conjugated scaffold. We present the synthesis and properties of DHA-BsubPc conjugates with varying peripheral substituents on the BsubPc core, being either unsubstituted (H12BsubPc) or partially fluorinated (F6BsubPc). Fluorination of the BsubPc core provided a remarkable increase in the reversibility of the DHA-VHF interconversions promoted by light and heat, respectively, and accompanied by on/off switching of the BsubPc fluorescence. Synthetically, the units were connected using Sonogashira coupling reactions of suitable acetylenic building blocks.

AB - In this work, we have linked the dihydroazulene (DHA)/vinylheptafulvene (VHF) photo-/thermoswitch and the boron subphthalocyanine (BsubPc) fluorophore via an axial oligo(phenyleneethynylene) bridging unit into new DHA-BsubPc conjugates. The objectives were to elucidate the influence of BsubPc on the DHA/VHF switching reactions and the influence of DHA/VHF on the BsubPc fluorescence in these conjugates for which the entire axial substituent connected to boron comprises one large, conjugated scaffold. We present the synthesis and properties of DHA-BsubPc conjugates with varying peripheral substituents on the BsubPc core, being either unsubstituted (H12BsubPc) or partially fluorinated (F6BsubPc). Fluorination of the BsubPc core provided a remarkable increase in the reversibility of the DHA-VHF interconversions promoted by light and heat, respectively, and accompanied by on/off switching of the BsubPc fluorescence. Synthetically, the units were connected using Sonogashira coupling reactions of suitable acetylenic building blocks.

KW - chromophores

KW - cross-coupling

KW - fluorescence

KW - molecular electronics

KW - photochromism

U2 - 10.1002/ejoc.202300284

DO - 10.1002/ejoc.202300284

M3 - Journal article

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SN - 1434-193X

VL - 26

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

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