|
|||||
|
|
Dihydroazulene-Boron Subphthalocyanine Conjugates with Oligo(phenyleneethynylene) Bridging Unit: Photoswitchable Fluorophores |
|
| Authors: | Dr Esmeralda Bukuroshi Dr Anne Ugleholdt Petersen Cecilie Jensen Mathias Kirkholt Lund Dr Martin Kühnel Prof Dr Kasper Nørgaard Prof Dr Timothy P Bender Prof Dr Mogens Brøndsted Nielsen |
| Institution: | 1. Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, Ontario, M5S 3E4 Canada
Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark These authors contributed equally (shared first-authorship);2. Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark These authors contributed equally (shared first-authorship);3. Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark;4. Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, Ontario, M5S 3E4 Canada |
| 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. |
| Keywords: | chromophores cross-coupling fluorescence molecular electronics photochromism |