Photochromism of Rotation‐Hindered Furylfulgides Influenced by Steric Modifications

Strübe, Frank; Siewertsen, Ron; Sönnichsen, Frank D.; Renth, Falk; Temps, F.; Mattay, Jochen

doi:10.1002/ejoc.201001649

Cited by 31 publications

(49 citation statements)

References 46 publications

(41 reference statements)

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“…The synthesis of the benzothiophene fulgide 37 was performed according to the experimental protocol of Stobbe et al. and Mattay et al ,. The challenging step, the Stobbe condensation, was accomplished by enolization of isopropylidenesuccinate and subsequent reaction with 34 .…”

Section: Resultsmentioning

confidence: 99%

Photochromic Dopamine Receptor Ligands Based on Dithienylethenes and Fulgides

Lachmann

Studte

Männel

et al. 2017

Chemistry A European J

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We describe the incorporation of the well-investigated class of photochromic dithienylethenes (DTEs) and fulgides into known dopamine receptor ligands such as 1,4-disubstituted aromatic and hydroxybenzoxazinone piperazines as well as aminoindanes. Subtype and functional selective photochromic ligands were obtained and characterized by NMR and UV/VIS spectroscopic measurements. The photophysical properties of the DTE based dopamine ligands revealed a high fatigue resistance for the diarylmaleimides, but the ringclosure could not be accomplished in polar solvents due to a known twisted intramolecular charge transfer (TICT). Several cyclopentene-DTEs showed high PSS, but a fast degradation by forming an irreversible byproduct. Focusing on the fulgides, high photostationary states and switching in polar solvents were possible. The compounds 43, 45 and 46 containing the isopropyl group showed only isomerization between the open E-form and the closed C-form. At a concentration of 1 nm, the cyclopentene-DTE 29-open showed a more than 11-fold higher activation of D , a pharmacologically important G protein-coupled receptor, than its photochromic congener 29-closed. Interestingly, the fulgimide-based pair 52-(E)-open/52-closed could be discovered as an alternative photoswitch with inverse activation properties exhibiting four-fold higher activity in the closed state.

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Section: Resultsmentioning

confidence: 99%

Photochromic Dopamine Receptor Ligands Based on Dithienylethenes and Fulgides

Lachmann

Studte

Männel

et al. 2017

Chemistry A European J

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“…One drawback of the synthesized fulgides is the undesired photoisomerization between the open (E)-and (Z)-forms upon irradiation, which could be proved for compound 30. [21] This competitive reaction to the EǞC ring closing reaction could be a reason for the weak modulation of the emission. Additionally, the absorption spectra of the (C)-forms still exhibit an intense absorption in the region of the absorption maxima of the (E)-forms.…”

Section: Photochemistrymentioning

confidence: 99%

Functionalized Fulgides and Fluorophore‐Photoswitch Conjugates

2011

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Various fulgides based on benzofuryl and indolyl core units with versatile functionalities were synthesized. Substitution at the phenylic site shows only small effects on the photochromic properties compared to the parent compounds 30 and 31. Fulgide–dye conjugates were prepared based on anthryl and coumaryl moieties. Fluorophores were introduced to the fulgide via substitution reaction or copper‐catalyzed azide‐alkyne cycloaddition (CuAAC). The synthesized conjugates show weak fluorescence and quenching properties in solution.

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“…The thermal stability of these compounds has been attributed to the methyl groups present on the hexatriene system . Introducing a more sterically demanding group, such as isopropyl, at position R 1 allowed exclusively for O E /C‐isomerization . Further photophysical properties, including PSS, quantum yield (QY) and absorption wavelength, have been reported to be influenced by the heteroaromatic system within the fulgimide (Table ).…”

Section: Chemical Investigations Of Fulgimidesmentioning

confidence: 99%

Fulgimides as Light‐Activated Tools in Biological Investigations

2019

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With high spatiotemporal control, the conformation, rigidity and electronics of photoresponsive bioactive molecules can be altered. This, in turn, allows for control over the biological properties of these molecules. Incorporation of a photoswitchable moiety into a number of reported inhibitors, ligands and modulators has demonstrated the ability to modulate enzyme, receptor and ion channel responses using light. To date, the major classes of photoswitches explored in biological applications have been the azobenzenes and diarylethenes. Even though the use of these photoswitches has established the value of photoresponsive molecules as biological tools, several limitations have become apparent. Fulgimides represent a promising class of photoswitches that are not widely used for such biological purposes. Their properties are similar to that of diarylethenes, as their photochromism is based on a 6π‐electrocyclic rearrangement, however, fulgimides have the added advantage of thermal stability for both isomers. Fulgimides exhibit high photostationary states and fatigue resistance, with the ability to switch in aqueous buffer solutions. In this minireview, these advantageous photophysical properties will be discussed, as well as the use of fulgimides in biological investigations.

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Photochromism of Rotation‐Hindered Furylfulgides Influenced by Steric Modifications

Cited by 31 publications

References 46 publications

Photochromic Dopamine Receptor Ligands Based on Dithienylethenes and Fulgides

Photochromic Dopamine Receptor Ligands Based on Dithienylethenes and Fulgides

Functionalized Fulgides and Fluorophore‐Photoswitch Conjugates

Fulgimides as Light‐Activated Tools in Biological Investigations

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