Synthesis and properties of new 9,10-anthraquinone derived compounds for molecular electronics

Seidel, Nadine; Hahn, Torsten; Liebing, Simon; Seichter, Wilhelm; Kortus, Jens; Weber, Edwin

doi:10.1039/c2nj40772h

Cited by 33 publications

(39 citation statements)

References 57 publications

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“…[1][2][3][4] The devices' overall charge-transport properties are expected to depend significantly on the conductance through individual nanoparticle-molecule-nanoparticle junctions. [8][9][10][11][12] These rely on only minor changes of the molecular structure and rather on a rearrangement of the bridge's p system, which should lead to fast switching. Such calculations have proven helpful in several studies on single-molecule conductance switching, in particular on anthraquinone/hydroquinone electrochemical systems.…”

Section: Introductionmentioning

confidence: 99%

“…Such calculations have proven helpful in several studies on single-molecule conductance switching, in particular on anthraquinone/hydroquinone electrochemical systems. [8][9][10][11][12] These rely on only minor changes of the molecular structure and rather on a rearrangement of the bridge's p system, which should lead to fast switching. We take a related approach, in which free electron pairs of an amine group taking part in the p system is switched off through creating a bond, thus removing a p site.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Controlling Molecular Conductance: Switching Off π Sites through Protonation

Schlicke¹,

Herrmann²

2014

ChemPhysChem

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Conductance switching through chemical modification of a molecular bridge is a major goal in molecular electronics, with the potential to lead to molecule-based functional devices. In terms of switching speed, mechanisms that rely on only minor rearrangements of molecular structures are particularly promising. We demonstrate, based on density functional theory calculations combined with a coherent tunneling approach, how protonation and deprotonation of amine-substituted or amine-bridged model molecular wires can switch off and on π-sites and thus: a) remove or introduce interference features in the electron transmission, and b) decrease or increase coupling along a chain. This mechanism may also be relevant for interactions between molecular bridges and metal cations, for example, in sensor applications.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Controlling Molecular Conductance: Switching Off π Sites through Protonation

Schlicke¹,

Herrmann²

2014

ChemPhysChem

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“…1,4‐Diamino anthraquinone ( 1 ) was diazotized with tert‐butyl nitrite followed by quenching with anhydrous copper(II) bromide to form 1,4‐dibromoanthraquinone ( 2 ) . The Stille coupling reaction between the purified 1,4‐dibromo anthraquinone and 4‐octyl‐2‐trimethyl stannyl thiophene gave compound 3 in 62.5% yield, subsequently brominated with NBS resulted in 1,4‐bis(5‐bromo‐4‐octylthiophen‐2‐yl)anthracene‐9,10‐dione ( 4 ).…”

Section: Resultsmentioning

confidence: 99%

Orange to green switching anthraquinone‐based electrochromic material

Bini

Gedefaw

Pan

et al. 2019

J of Applied Polymer Sci

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An easily accessible anthraquinone‐benzodithiophene‐based high bandgap polymer (PTAq) was synthesized by Stille coupling reactions in remarkably high yield (96.5%). The highest occupied molecular orbital energy level of the polymer was estimated from the onset of oxidation in a cyclic voltammetry study to be −5.7 eV. PTAq showed an orange‐to‐green color switching with the application of a 1.0‐V external potential to the polymer film, which was visible to the naked eye. The optical behavior change was also monitored using ultraviolet–visible absorption spectroscopy and revealed a respectable 75% transmittance change when the polymer film was subjected to a 1.0‐V external potential. The high color contrast observed makes PTAq one of the most promising materials for electrochromic device applications. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47729.

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“…Another route utilized anthraquinone analogs bearing acetylene and sulfur-containing residues in the presence of diisopropylamine (DIPA) [9]. Here, the yield of the 2,6-bis(thiophene-3-ylethynyl)-9,10-anthraquinone product was 90 %, depending on the available dibromide starting material that was used ( Figure 3).…”

Section: Synthesis Of Acetylenequinonesmentioning

confidence: 99%

Fundamental and Applied Aspects of the Chemistry of Acetylenylquinones

Vasilevsky¹,

Stepanov²

2020

REFFIT

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In addition to the reported synthetic routes for the acetylene derivatives of quinones, a detailed analysis of the fundamental chemical, physicochemical, and biological properties of this class of compounds is presented herein. The advantages of Pd- and Cu-catalyzed cross-coupling of terminal alkynes with iodarenes via the Sonogashira reaction to produce new acetylenylquinones with predetermined properties are examined. Here, combining quinoid and acetylene residues into one molecule gives the resulting compounds chemical specificity, as demonstrated by several reported examples of non-trivial transformations. In particular, the presence of the quinoid cycle significantly increases the electrophilicity of the triple bond and determines the range of transformation possibilities. Moreover, acetylenylquinones have heightened sensitivity to both external (such as the reaction temperature and the nature of the solvent) and internal (e.g., the structure of substituents in the nucleus and the acetylene fragment) factors. For example, regioselective cleavage of a strong triple bond under the action of amines is possible in the absence of a metal catalyst. Peri-substituted acetylenyl-9,10-anthraquinones are most suited for the synthetic route because of the proximity of the acetylene and carbonyl groups. Mechanisms of reactions of selective alkynylquinones are described.

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Synthesis and properties of new 9,10-anthraquinone derived compounds for molecular electronics

Cited by 33 publications

References 57 publications

Controlling Molecular Conductance: Switching Off π Sites through Protonation

Controlling Molecular Conductance: Switching Off π Sites through Protonation

Orange to green switching anthraquinone‐based electrochromic material

Fundamental and Applied Aspects of the Chemistry of Acetylenylquinones

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