Dihydroazulene-Boron Subphthalocyanine Conjugates with Oligo(phenyleneethynylene) Bridging Unit: Photoswitchable Fluorophores
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Dihydroazulene-Boron Subphthalocyanine Conjugates with Oligo(phenyleneethynylene) Bridging Unit : Photoswitchable Fluorophores. / Bukuroshi, Esmeralda; Ugleholdt Petersen, Anne; Jensen, Cecilie; Kirkholt Lund, Mathias; Kühnel, Martin; Nørgaard, Kasper; Bender, Timothy P.; Brøndsted Nielsen, Mogens.
I: European Journal of Organic Chemistry, Bind 26, Nr. 24, e202300284, 2023.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Dihydroazulene-Boron Subphthalocyanine Conjugates with Oligo(phenyleneethynylene) Bridging Unit
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
N1 - Publisher Copyright: © 2023 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.
PY - 2023
Y1 - 2023
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
AN - SCOPUS:85159792929
VL - 26
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 24
M1 - e202300284
ER -
ID: 355199581