Synthesis and photochromic properties of tetrakis(3,5-dimethyl-2-thienyl)- and tetrakis(2,5-dimethyl-3-thienyl)ethylenes

Беленький, Л. И.; Gromova, G. P.; Колотаев, А. В.; Nabatov, B. V.; Krayushkin, M. M.

doi:10.1007/s11172-005-0382-5

Cited by 10 publications

(3 citation statements)

References 14 publications

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“…Among the dendritic macromolecules, thiophene-containing dendrimers as an important class of promising materials have received tremendous attention in recent decades . Since the first all-thiophene dendrimers up to a 15- and a 30-mer were prepared by Advicula and co-workers; various oligothiophene-based dendrimers having different cores and branches have also been reported. − Most of these dendrimers were synthesized with the dendron of terthiophene ( 3T ). ,− Since, π-conjugated branched oligothiophenes showed tremendous challenges in synthetic organic chemistry and a promising outcome in organic electronics. , To design and construct a new class of dendritic architectures, two novel and hyperbranched dendrimers, 16T and 20T (Figure ), based on tetrakis(thiophene-2-yl)ethene ( 4T ) as a dendron, were synthesized using carbonylation, Suzuki, and McMurry reactions in our work. In addition, preliminary spectroscopic and electrochemical data are discussed.…”

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confidence: 99%

Synthesis of Dendrimers Based on Tetrakis(thiophene-2-yl)ethene as New Dendron

Shi

et al. 2013

Org. Lett.

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Two novel dendrimers, 16T and 20T, based on 1,1,2,2-tetra(thiophen-2-yl)ethene (4T) as a new dendron, were efficiently synthesized via carbonylation, Suzuki, and McMurry reactions. All intermediates and title compounds were fully characterized by (1)H NMR, (13)C NMR, and HRMS. 4T and 16T were confirmed by X-ray single crystal analyses. In addition, the absorption behaviors of two titled dendrimers are also described.

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confidence: 99%

Synthesis of Dendrimers Based on Tetrakis(thiophene-2-yl)ethene as New Dendron

Shi

et al. 2013

Org. Lett.

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“…The former is known as a prominent member of organic photochromic materials. The latter is attractive for the aggregation-induced emission (AIE) effect. − The extraordinary antiaggregation causing the quench effect enables tetraphenylethylenes to have potential application in diverse biolabels, bioprobes, fluorescence sensors, and photoelectronic devices. − In view of their complementary performances in fluorescent emission, several diarylethene derivatives connected tetraphenylethylene building blocks and tetrathienylethenes have been reported for multifunctional molecules in recent years. − It is the most common protocol for the design of multifunctional molecules by bonding two or more building blocks with different functionalities together after various chemical or physical modifications. It often works, but sometimes the different units may interfere with each other in functions.…”

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confidence: 96%

Hybrid cis/trans Tetra-arylethenes with Switchable Aggregation-Induced Emission (AIE) and Reversible Photochromism in the Solution, PMMA Film, Solid Powder, and Single Crystal

et al. 2017

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How to efficiently design and synthesize multifunctional molecules is particularly challenging. In this presentation, we devote to constructing a kind of simple structures with composite functionalities through straightforward preparation. Starting from common commercially available materials, the titled cis/trans-tetraarylethenes can be conveniently obtained by a one-pot process under mild conditions. The different configurations were confirmed by H NMR and single crystal data analysis. The trans-tetraarylethenes could be converted into cis-forms not only by photoirradiation but also by microwave irradiation, which provided us a new choice for isomeric conversion, especially in relation to light sensitivity. Results show that all the hybrid cis/trans-isomers performed switchable fluorescence and reversible photochromism in solution, PMMA film, solid powder, and single crystal. Moreover, these hybrid tetraarylethenes could be utilized as photoswitchable media to tune the behavior of aggregation-induced emission (AIE) and aggregation-caused quenching (ACQ). These versatile properties are favorable for the potential applications in fluorescent photoswitches, nondestructive readout, and logic gates. We hope that our design strategy could provide a new protocol for constructing a kind of multifunctional molecules based some simple structure and convenient synthetic procedures.

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“…The synthesis of tetrakis has been previously reported by Krayushkin et al 10 who qualitatively investigated its photochromic properties. They observed photocolouration (l max = 451 nm, for the coloured form) and fluorescence emission (l max = 400 nm) from the colourless form in acetonitrile solution.…”

Section: Introductionmentioning

confidence: 99%

Tetra- and tri-thienyl ethenes: new fluorescent photochromic compounds

Cipolloni

Ortica

Bougdid

et al. 2011

Photochem Photobiol Sci

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In this work the photochemistry and photophysics of two new ethenic compounds, a tetra-thienylethene (tetrakis) and a tri-thienylethene (triakis), have been investigated by steady state and time-resolved UV-vis absorption and luminescence spectroscopies. The quantum yields of the UV-photoinduced ring-closure reaction (Φ(O→C)) and of the visible-stimulated cycloreversion reaction (Φ(C→O)) were determined as a function of the temperature in 3-methylpentane. The trends of Φ(O→C) and Φ(C→O) with temperature suggest that a barrier exists to the ring opening reaction which hampers the cycloreversion in a rigid matrix at 80 K. For the closure reaction, a negative effect of the temperature on Φ(O→C) reflects an increased concentration of the more easily isomerizable antiparallel conformer with decreasing the temperature. Quantum yields and lifetimes of fluorescence, observed for tetrakis in both the colourless and coloured forms and for triakis only for the coloured form, were determined. The solvent and temperature effects on fluorescence were investigated. Nanosecond time-resolved experiments showed the formation of a triplet transient from tetrakis which could be a precursor of the main reaction photoproduct. For triakis no transient was detected.

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Synthesis and photochromic properties of tetrakis(3,5-dimethyl-2-thienyl)- and tetrakis(2,5-dimethyl-3-thienyl)ethylenes

Abstract: Tetrakis(3,5 dimethyl 2 thienyl)ethylene and tetrakis(2,5 dimethyl 3 thienyl)ethylene were obtained from the corresponding dithienyl ketones by the McMurry reaction. The photo chromic properties of the compounds obtained were studied.

Cited by 10 publications

References 14 publications

Synthesis of Dendrimers Based on Tetrakis(thiophene-2-yl)ethene as New Dendron

Synthesis of Dendrimers Based on Tetrakis(thiophene-2-yl)ethene as New Dendron

Hybrid cis/trans Tetra-arylethenes with Switchable Aggregation-Induced Emission (AIE) and Reversible Photochromism in the Solution, PMMA Film, Solid Powder, and Single Crystal

Tetra- and tri-thienyl ethenes: new fluorescent photochromic compounds

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