Microwave-assisted synthesis of symmetric and asymmetric viologens

Lamberto, Massimiliano; Rastede, Elizabeth E.; Decker, Justyne; Raymo, Françisco M.

doi:10.1016/j.tetlet.2010.08.070

Cited by 23 publications

(12 citation statements)

References 19 publications

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“…The viologen-arranged molecules with ω-mercaptodecyl groups were prepared via a microwave-heating technique 35 . The synthetic route of B3 is shown in Supplementary Scheme S1, and the procedures are described below.…”

Section: Methodsmentioning

confidence: 99%

Conical Gradient Junctions of Dendritic Viologen Arrays on Electrodes

Kawauchi

Oguchi

Nagai

et al. 2015

Sci Rep

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The three-dimensional construction of arrays of functional molecules on an electrode surface, such as organic semiconductors and redox-active molecules, is a considerable challenge in the fabrication of sophisticated junctions for molecular devices. In particular, well-defined organic layers with precise molecular gradients are anticipated to function as novel metal/organic interfaces with specific electrical properties, such as a space charge layer at the metal/semiconductor interface. Here, we report a strategy for the construction of a three-dimensional molecular array with an electrical connection to a metal electrode by exploiting dendritic molecular architecture. Newly designed dendritic molecules consisting of viologens (1,1′-disubstituted-4,4′-bipyridilium salts) as the framework and mercapto groups as anchor units form unique self-assembled monolayers (SAMs) on a gold surface reflecting the molecular design. The dendritic molecules exhibit a conical shape and closely pack to form cone arrays on the substrate, whereas, in solution, they expand into more flexible conformations. Differences in the introduction position of the anchor units in the dendritic structure result in apical- and basal-type cone arrays in which the spatial concentration of the viologen units can be precisely configured in the cones. The concentration in apical-type SAMs increases away from the substrate, whereas the opposite is true in basal-type SAMs.

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Section: Methodsmentioning

confidence: 99%

Conical Gradient Junctions of Dendritic Viologen Arrays on Electrodes

Kawauchi

Oguchi

Nagai

et al. 2015

Sci Rep

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“…17 To enhance the solubility of 1 18 and to introduce electron-accepting properties, n -dodecyl alkyl chains were introduced at the pyridyl nitrogens (for synthetic details, see ESI†). In analogy to the reaction conditions optimized for the dialkylation of related 4,4′-bipyridines, so-called viologens, 19 reaction of 1 with 1-bromododecane at 130 °C in N , N -dimethylformamide (DMF) under microwave irradiation furnished the N , N ′-didodecyl decorated 3,10-diazapicenium dibromide salt 2 in 89% yield (Scheme 1). To study the impact of the counterion on the photophysical and electrochemical properties, anion exchange reactions were carried out.…”

Section: Resultsmentioning

confidence: 99%

p-Doping of graphene in hybrid materials with 3,10-diazapicenium dications

et al. 2017

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“…grade from Acros and Beijing Chemical Factory, respectively, which were used without further purification. Ethyl viologen dibromide was prepared according to the previously Materials Research Bulletin 48 (2013) 595-602 reported method [24]. Syntheses of the two bipolar hemicyanines of [Me 2 N-C 6 H 4 -CH5 5CH-C 5 H 4 N + -(CH 2 ) n -+ NC 5 H 4 -CH5 5CH-C 6 H 4 -NMe 2 ]Br 2 (n = 3, A 3 Br 2 ; n = 6, A 6 Br 2 ) (see Fig.…”

Section: Methodsmentioning

confidence: 99%