Sequential Functionalisation of Bis-Protected Tetrathiafulvalene-dithiolates

Simonsen, Klaus B.; Svenstrup, Niels; Lau, Jesper; Simonsen, O.; Mørk, Pernille; Kristensen, Gitte J.; Becher, Jan

doi:10.1055/s-1996-4216

Cited by 178 publications

(151 citation statements)

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“…Compound 1 and the related macrocycle 2 were synthesized as illustrated in Scheme 1 from the cyanoethyl derivatives 3 and 5 (22)(23)(24). TTF is a well known -donor that forms one-dimensional conducting columns through -interaction in the partially oxidized state and exhibits high electrical conduction along the TTF stacking direction (18)(19)(20)(21).…”

mentioning

confidence: 99%

Formation of oriented molecular nanowires on mica surface

Akutagawa

Ohta

Hasegawa

et al. 2002

Proc. Natl. Acad. Sci. U.S.A.

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Molecular ''nanowire'' structures composed of the charge transfer complex of a bis-tetrathiafulvalene substituted macrocycle and tetrafluorotetracyanoquinodimethane were constructed on mica substrates by employing the Langmuir-Blodgett technique. The nanowires transferred from a dilute aqueous potassium chloride subphase had typical dimensions of 2.5 nm ؋ 50 nm ؋ 1 m. The nanowires are oriented to specific directions, corresponding to the directions of the potassium-ion array on the mica surface having sixfold symmetry. Such correlation between the nanowires and the substrate surface was also observed when a dilute aqueous rubidium chloride subphase was used. On the other hand, the correlation completely disappeared when the subphase contained divalent cations, indicating that the molecular nanowires orient by recognizing the monocation array on the mica surface. The nanowires formed by the vertical dipping method coexist with the monolayers. Only nanowire structures are, however, observed when we apply the horizontal lifting method. Based on the crystal structure of a related complex, a possible structure of the nanowires is presented. The conductivity of the nanowires was estimated to be of the order of 10 ؊3 S⅐cm ؊1 . The nanowires formed specific (regular) structures such as T-shape junctions, suggesting their use in construction of future molecular nanoscale devices.

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mentioning

confidence: 99%

Formation of oriented molecular nanowires on mica surface

Akutagawa

Ohta

Hasegawa

et al. 2002

Proc. Natl. Acad. Sci. U.S.A.

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“…All reagents and solvents employed for the syntheses were of high purity grade and were purchased from Sigma-Aldrich Co. (St Louis, MO, USA), Merck (Darmstadt, Germany), and SDS, except compound 3 [18] and 4 [19] which were synthesized according to literature procedures Anhydrous solvents were used in the chemical reactions and for recording the cyclic voltammograms. 1 H NMR spectra were recorded using a Bruker Avance 250, 400, or 500 instruments (Bruker, Billerica, MA, USA) and Me 4 Si was used an internal standard.…”

Section: General Methods For Synthesis and Characterizationmentioning

confidence: 99%

“…First, the cross-coupling of the ethylendithio-thione (3) [18] and 5-tosyl-(1,3)-dithiolo [4,5-c]pyrrole-2-one (4) [19] in anhydrous (EtO) 3 P gave 5 in 82% yield after column chromatography. Subsequently, the tosyl protecting group on derivative 5 was removed using NaOMe in a THF/MeOH mixture to obtain compound 6 as a yellow solid which was used in the next reaction without further purification.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and Characterization of Ethylenedithio-MPTTF-PTM Radical Dyad as a Potential Neutral Radical Conductor

et al. 2016

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During the last years there has been a high interest in the development of new purely-organic single-component conductors. Very recently, we have reported a new neutral radical conductor based on the perchlorotriphenylmethyl (PTM) radical moiety linked to a monopyrrolotetrathiafulvalene (MPTTF) unit by a π-conjugated bridge (1) that behaves as a semiconductor under high pressure. With the aim of developing a new material with improved conducting properties, we have designed and synthesized the radical dyad 2 which was functionalized with an ethylenedithio (EDT) group in order to improve the intermolecular interactions of the tetrathiafulvalene (TTF) subunits. The physical properties of the new radical dyad 2 were studied in detail in solution to further analyze its electronic structure.

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“…The target ligand L (Scheme 1) was prepared by deprotection of the thiol function of the 4,5-dicarboxylic acid-4′,5′-bis(2-cyanoethyl)thio)-tetrathiafulvalene-, dimethyl ester [59] with sodium methoxide or cesium hydroxide and then grafting of the 2-methylpyridine-1-oxide coordinating groups. Scheme 1.…”

Section: Synthesismentioning

confidence: 99%

“…General Procedures and Materials: The precursors Ln(hfac)3·2H2O (Ln = Dy [71] and the 4,5-dicarboxylic acid-4′,5′-bis(2-cyanoethyl)thio)-tetrathiafulvalene-, dimethyl ester [59] were synthesised following previously reported methods. All other reagents were purchased from Aldrich Co., Ltd. (Saint-Quentin Fallavier, France) and used without further purification.…”

Section: Synthesismentioning

confidence: 99%