Dihydroazulene-Boron Subphthalocyanine Conjugates with Oligo(phenyleneethynylene) Bridging Unit: Photoswitchable Fluorophores
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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.
Originalsprog | Engelsk |
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Artikelnummer | e202300284 |
Tidsskrift | European Journal of Organic Chemistry |
Vol/bind | 26 |
Udgave nummer | 24 |
Antal sider | 9 |
ISSN | 1434-193X |
DOI | |
Status | Udgivet - 2023 |
Bibliografisk note
Funding Information:
The authors acknowledge the support from a Mitacs Globalink Research Award and Natural Sciences and Engineering Research Council (NSERC) Postgraduate Scholarship (Doctoral Program) to E.B. at the University of Toronto. The Independent Research Fund Denmark|Natural Sciences (#8021‐00009B) and The Independent Research Fund Denmark, Technology and Production Sciences (#0136‐00081B) are acknowledged for financial support.
Publisher Copyright:
© 2023 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.
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