Dihydroazulene‐Boron Subphthalocyanine Conjugates with Oligo(phenyleneethynylene) Bridging Unit: Photoswitchable Fluorophores-Reference-Cited by-同舟云学术

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

Published:2023-05-22 Issue:24 Volume:26 Page:
ISSN:1434-193X
Container-title:European Journal of Organic Chemistry
language:en
Short-container-title:Eur J Org Chem

Author:

Bukuroshi Esmeralda¹²,Ugleholdt Petersen Anne²,Jensen Cecilie²,Kirkholt Lund Mathias²,Kühnel Martin²^ORCID,Nørgaard Kasper²^ORCID,Bender Timothy P.¹³⁴^ORCID,Brøndsted Nielsen Mogens²^ORCID

Affiliation:

1. Department of Chemical Engineering and Applied Chemistry University of Toronto 200 College Street Toronto Ontario M5S 3E4 Canada

2. Department of Chemistry University of Copenhagen Universitetsparken 5 DK-2100 Copenhagen Ø Denmark

3. Department of Chemistry University of Toronto 80 St George Street Toronto Ontario M5S 3H6 Canada

4. Department of Materials Science and Engineering University of Toronto 184 College Street Toronto Ontario M5S 3E4 Canada

Abstract

AbstractIn 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.

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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