Functionalized Fulgides and Fluorophore‐Photoswitch Conjugates

Strübe, Frank; Rath, Susann; Mattay, Jochen

doi:10.1002/ejoc.201100228

Cited by 22 publications

(18 citation statements)

References 32 publications

(17 reference statements)

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“…These include higher thermal stability, longer lifetimes of the photocolored forms and higher yields of the photocoloration reactions and better persistance to photodegradation. It has been shown that annulation of benzene rings to the five-membered rings of pyrryl, thienyl and furanyl fulgides can promote the additional improvement of these properties [10,[18][19][20][21]. In accordance with these data, we have previously synthesized and studied the photochromic properties of 2-benzo[b]thienylfulgides [22].…”

Section: Introductionmentioning

confidence: 76%

Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides

Rybalkin¹,

Zmeeva²,

Попова³

et al. 2020

Beilstein J. Org. Chem.

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2-Benzo[b]thienyl fulgides and fulgimides containing bulky diphenylmethylene substituents were synthesized in the form of their ring-opened E- or Z-isomers. In contrast to the majority of known fulgides/fulgimides, that form colored ring-closed structures under UV irradiation, the obtained compounds undergo an irreversible transformation leading to decoloration of their solutions. This rearrangement with the formation of the dihydronaphthalene core appeared to be by 2–3 orders of magnitude more efficient than for the known diphenylmethylene(aryl(hetaryl))fulgides. The molecular structures of E- and Z-isomers and of products of the photoinduced rearrangement completed by 1,5-H shift reaction, 3a,4-dihydronaphtho[2,3-c]furans(pyrroles) C, were established based on the data of 1H and 13C NMR spectroscopy and X-ray diffraction studies.

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Section: Introductionmentioning

confidence: 76%

Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides

Rybalkin¹,

Zmeeva²,

Попова³

et al. 2020

Beilstein J. Org. Chem.

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“…The synthesis of quinone 11 started with the known benzofuran 8 , readily prepared from benzoquinone in a Nenitzescu type reaction. 33 Methylation gave the known 5-methoxy derivative 9 , nitration of which gave a mixture of the desired 4-nitro compound 10 along with its 6-nitro isomer in excellent overall yield, but in a 1:2 ratio. Although nitrobenzofuran 10 could be isolated, it was more convenient to reduce the mixture of nitro compounds to the corresponding amines, reduce the ketone with sodium borohydride and then oxidize the aniline with Fremy’s salt and purify the desired quinone 11 at the final stage (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…3-Acetyl-5-hydroxy-2-methylbenzofuran 8 33 (1.62 g, 8.5 mmol) in DMF (30 mL) was added to a stirring suspension of potassium hydride (0.61 g, 15.2 mmol) in DMF (50 mL) at 0 °C. The mixture was stirred at room temperature for 45 min.…”

Section: Methodsmentioning

confidence: 99%

Benzofuran-, benzothiophene-, indazole- and benzisoxazole-quinones: Excellent substrates for NAD(P)H:quinone oxidoreductase 1

Newsome

Hassani

Swann

et al. 2013

Bioorganic & Medicinal Chemistry

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A series of heterocyclic quinones based on benzofuran, benzothiophene, indazole and benzisoxazole has been synthesized, and evaluated for their ability to function as substrates for recombinant human NAD(P)H:quinone oxidoreductase (NQO1), a two-electron reductase upregulated in tumor cells. Overall, the quinones are excellent substrates for NQO1, approaching the reduction rates observed for menadione

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“…The purity of this compound was confirmed by 1 H NMR spectroscopy and was used as supplied. All other photoswitches were synthesized following published methods; Azo1,[25] CF 3 -fulgide, [39,40] and SP1 [26].…”

Section: Methodsmentioning

confidence: 99%

A comparative study of the fluorescence and photostability of common photoswitches in microstructured optical fibre

Stubing

Heng

Monro

et al. 2017

Sensors and Actuators B: Chemical

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 If accepted for publication, we encourage authors to link from the preprint to their formal publication via its Digital Object Identifier (DOI). Millions of researchers have access to the formal publications on ScienceDirect, and so links will help your users to find, access, cite, and use the best available version. Authors can update their preprints on arXiv or RePEc with their accepted manuscript. Please note: Cell Press, The Lancet, and some society-owned titles have different preprint policies. Information on these is available on the journal homepage. Preprints should not be added to or enhanced in any way in order to appear more like, or to substitute for, the final versions of articles. December 2016Fluorescence Abstract:The fluorescence spectra and photostability under 532 nm laser excitation of four different common photoswitches (an azobenzene, spiropyran, indolylfulgide, and a diarylperfluorocyclopentene) was investigated in a silica microstructured optical fibre. An example of each photoswitch was examined both in solution as well as physically adsorbed to the silica fibre surface. This comparison was made to determine any fluorescence behavioral differences as a result of each solution and the optical fibre fluorescence sensing platform, and to determine which photoswitch has the best performance in this light intense microenvironment. It was found that the azobenzene and the spiropyran showed the most favorable behavior; showing a stronger fluorescence response and the least degradation of the fluorescence signal.

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Functionalized Fulgides and Fluorophore‐Photoswitch Conjugates

Cited by 22 publications

References 32 publications

Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides

Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides

Benzofuran-, benzothiophene-, indazole- and benzisoxazole-quinones: Excellent substrates for NAD(P)H:quinone oxidoreductase 1

A comparative study of the fluorescence and photostability of common photoswitches in microstructured optical fibre

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