A Contribution to the Design of Molecular Switches:  Novel Acid-Mediated Ring-Closing−Photochemical Ring-Opening of 2,3-Bis(heteroaryl)quinones (Heteroaryl = Thienyl, Furanyl, Pyrrolyl)

Deng, Xiaohu; Liebeskind, Lanny S.

doi:10.1021/ja0106220

Cited by 89 publications

(75 citation statements)

References 8 publications

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“…Among these are reductive coupling of carbonyl precursors according to the McMurry reaction [11] with TiCl 4 /Zn as the reducing system, [12][13][14] Stille coupling, [15] and Suzuki cross-coupling. [13] For our purposes, the coupling of brominated aryl moieties to the double bond in perfluorinated cyclopentene with nBuLi as used in reference [10] was the method of choice.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Photoswitching Studies of Difurylperfluorocyclopentenes with Extended π‐Systems

Sysoiev

Fedoseev

Kim

et al. 2011

Chemistry A European J

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In an attempt to design molecular optoelectronic switches functioning in molecular junctions between two metal tips, we synthesized a set of photochromic compounds by extending the π-system of 1,2-bis-(2-methyl-5-formylfuran-3-yl)perfluorocyclopentene through suitable coupling reactions involving the formyl functions, thereby also introducing terminal groups with a binding capacity to gold. Avoiding the presence of gold-binding sulphur atoms in the photoreactive centre, as they are present in the frequently used analogous thienyl compounds, the newly synthesized compounds should be more suitable for the purpose indicated. The kinetics of reversible photoswitching of the new compounds by UV and visible light was quantitatively investigated in solution. The role of conformational flexibility of the π-system for the width of the UV/Vis spectra was clarified by using quantum chemical calculations with time-dependent (TD)-DFT. As a preliminary test of the potential of the new compounds to serve as optoelectronic molecular switches, monolayer formation and photochemical switching on gold surfaces was observed by using surface plasmon resonance.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Photoswitching Studies of Difurylperfluorocyclopentenes with Extended π‐Systems

Sysoiev

Fedoseev

Kim

et al. 2011

Chemistry A European J

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“…The reaction between organotin compounds and various electrophiles takes place under neutral conditions in the presence of catalytic amounts of palladium [24] and has a high degree of selectivity. Both symmetricaly [25,26] and unsymmetrically substituted quinones [26] can be obtained by this method. The usual catalyst is Pd(PPh 3 ) 4 .…”

Section: Reactions Of Haloquinones With Heteroarylstannanes Catalymentioning

confidence: 99%

“…of tributylstannylheteroarene with yields of ~70%. Diheteroarylbenzoquinones 3 with various substituents at positions 2 and 3 are produced according to the following scheme [25,26]: In the reaction of 2,5-dibromobenzoquinone with an excess of 3-indolylstannane under the standard conditions for the Stille reaction the monosubstituted product is formed initially, and the 2,5-disubstituted benzoquinone 4 is then formed more slowly [27]. By this two-stage method it is possible to obtain 2,5-bisindolylquinones with various alkyl substituents at the nitrogen atom.…”

Section: Reactions Of Haloquinones With Heteroarylstannanes Catalymentioning

confidence: 99%

Methods for the Synthesis of Heteroaryl-substituted 1,4-Benzo- and 1,4-Naphthoquinones. (Review)

Batenko¹,

Karlivans²,

Valters³

2005

Chem Heterocycl Compd

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Methods for the synthesis of heteroaryl-substituted 1,4-benzo-and 1,4-naphthoquinones with a C-C bond between the heterocycle and quinone fragments are reviewed.Benzoquinones and their derivatives are widely used in organic synthesis as synthons and reagents [1,2]. They are used as electron-accepting components for the production of charge-transfer complexes and radicalion salts [3,4]. Derivatives of benzoquinones, isolated from natural sources, are subunits in many biological processes, such as electron transport, the photosynthesis of plants, the coagulation of blood, and cell respiration [1, 2, 5]. Reviews have been published on the synthesis of hydroxyquinones [6] and 1,4-benzoquinones condensed with heterocycles [7,8], but methods for the synthesis of heteroaryl derivatives of 1,4-benzoquinones and 1,4-naphthoquinones where the fragments of the heterocycle and the quinone are linked by a C-C bond have not so far been reviewed. Heteroaryl-substituted benzoquinones have demonstrated anticancer [9-11], antifungal, and antibacterial characteristics [11] and antidiabetic activity [12]. The present review is devoted to the analysis and classification of methods for the production of these compounds. Methods for the synthesis of heteroaryl derivatives of quinones can be divided into three groups: The formation of a C-C bond between the quinone and the heterocycle, construction of the heterocycle on the basis of the quinone, and construction of the quinone on the basis of the heterocycle.

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“…During the past decades, there have been important achievements in the synthesis of new families of organic photochromic molecules [3,6,7]. For example, the diarylethenes having two thiophenes [8], furans [9] and thiazoles [10][11][12] exhibit excellent thermal stability, and the ones with two indoles, pyrrols, and benzenes are thermally unstable [12,13]. Nevertheless, the hexatriene backbones necessary for the versatility of the diarylethenes reported so far have been mostly limited to the fivemembered aryl rings.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties Study of 1-(2,4-dimethoxyl-5-pyrimidinyl)-2-[2-methyl-5-(3-methyl)-phenyl-3-thienyl] Perfluorocyclopentene

Liu¹,

Liu²,

Pu³

2016

Proceedings of the 2015 International Conference on Materials Chemistry and Environmental Protection (Meep-15)

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A Contribution to the Design of Molecular Switches: Novel Acid-Mediated Ring-Closing−Photochemical Ring-Opening of 2,3-Bis(heteroaryl)quinones (Heteroaryl = Thienyl, Furanyl, Pyrrolyl)

Cited by 89 publications

References 8 publications

Synthesis and Photoswitching Studies of Difurylperfluorocyclopentenes with Extended π‐Systems

Synthesis and Photoswitching Studies of Difurylperfluorocyclopentenes with Extended π‐Systems

Methods for the Synthesis of Heteroaryl-substituted 1,4-Benzo- and 1,4-Naphthoquinones. (Review)

Synthesis and Properties Study of 1-(2,4-dimethoxyl-5-pyrimidinyl)-2-[2-methyl-5-(3-methyl)-phenyl-3-thienyl] Perfluorocyclopentene

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