Efficient green light-excited switches based on dithienylethenes with BF₂-doped π-conjugated systems

Abstract

Novel dithienylethene derivatives with BF2-doped π-conjugation show efficient green light-excited photoswitching behaviors in solvents, PMMA film and living cells.

Visible Light‐Driven Molecular Switches and Motors: Recent Developments and Applications

“…Moreover, visible light‐driven switching of fluorescence has been observed in this luminescent compound. The fluorescent switching behavior of the compound has also been effectively achieved in living cells [120] . Compound 44 has been made to respond to visible light by extending π‐conjugation with electron donating groups [121] .…”

Der Lebensmittelfarbstoff Curcumin (E 100)

“…A. eine relativ hohe Elektronenaffinität [17], sodass sie z. B. als p-Dotanden zur Er-höhung der elektrischen Leitfähigkeit von organischen Verbindungen [18] -üblicherweise als organische Metalle bezeichnet -, zur Sensibilisierung von über Radikalionen ablaufende fotochemische Reaktionen [19] oder als Fotosensibilisatoren in elektrofotografischen Materialien eingesetzt werden können [20]. [23,24] sowie von organischen Schwefelverbindungen [25] sowie von Pikrinsäure [26].…”

Chloro- and BF2bdk-substituted dithienylethene: Synthesis, photophysical properties, and optical switching behavior

“…Accordingly, it was found that dithienylethene 1 exhibited solvent-dependent photochromic properties, which was in accordance with other BF 2 bdkcontaining dithienylethenes reported recently. [23][24][25][26][27][28] Upon alternating irradiation with blue/red light, the fluorescent switching behavior was also investigated in the above solvents at room temperature. As depicted in Figure 4(a), its luminescence intensity at 580 nm in CH 2 Cl 2 gradually decreased along with an obvious fading of the red fluorescence, which was due to efficient energy transfer from the excited difluoroboron β-diketonate moiety to the ringclosed dithienylethene skeleton.…”

“…[18][19][20][21][22] In consideration of their intriguing photophysical properties, our group has recently designed and synthesized a range of visible light-responsive difluoroboron β-diketonate (BF 2 bdk) complexes, based on a diarylethene unit via Knoevenagel condensation reactions. [23][24][25][26][27][28] Most of the obtained complexes demonstrated excellent visible light-controlled photochromic properties and fluorescence switching behavior in solution, polymethyl methacrylate (PMMA) film, and even in living cells. However, these asymmetric BF 2 bdk-functionalized dithienylethene derivatives normally required non-trivial multistep syntheses.…”