Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives

Vilela, Filipe; Skabara, Peter J.; Mason, Christopher R.; Westgate, Thomas D.; Luquín, Asunción; Coles, Simon J.; Hursthouse, Michael B.

doi:10.3762/bjoc.6.113

Cited by 10 publications

(5 citation statements)

References 33 publications

(41 reference statements)

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“…The cyclic voltammetry experiments were carried out to explore the electrochemical properties of the TTF compounds. The cyclic voltammograms of T 1 and T 2 were measured in dry and degassed dichloromethane solution [ 28 ]. Both T 1 and T 2 displayed two, reversible, one-electron redox couples, in which the first oxidation at = +0.628 V ( T 1 ) and +0.643 V ( T 2 ) (vs Ag/AgCl) was in the anodic window.…”

Section: Resultsmentioning

confidence: 99%

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

Sun

Lai

et al. 2015

Beilstein J. Org. Chem.

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SummaryThis paper reports the self-assembly of two new tetrathiafulvalene (TTF) derivatives that contain one or two urethane groups. The formation of nanoribbons was evidenced by scanning electron microscopy (SEM) and X-ray diffraction (XRD), which showed that the self-assembly ability of T 1 was better than that of T 2. The results revealed that more urethane groups in a molecule did not necessarily instigate self-assembly. UV–vis and FTIR spectra were measured to explore noncovalent interactions. The driving forces for self-assembly of TTF derivatives were mainly hydrogen bond interactions and π–π stacking interactions. The electronic conductivity of the T 1 and T 2 films was tested by a four-probe method.

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Section: Resultsmentioning

confidence: 99%

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

Sun

Lai

et al. 2015

Beilstein J. Org. Chem.

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“…An efficient method for the synthesis of 25c – a compound required for synthetic pathway B – was found to be repeated sequential lithiation of vinylene trithiocarbonate ( 26 ) [ 67 ] followed by subsequent trapping of the lithium organic species with thiophenecarboxaldehyde 27 [ 60 ]. The diol 25e , formed as a product of this reaction, is unstable and undergoes various rearrangments [ 68 – 69 ] in acidic conditions. Hence, it is preferably oxidised directly to the more stable diketone 25c without delay.…”

Section: Reviewmentioning

confidence: 99%

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

Kanibolotsky¹,

Findlay²,

Skabara³

2015

Beilstein J. Org. Chem.

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SummaryThe aim of this review is to give an update on current progress in the synthesis, properties and applications of thiophene-based conjugated systems bearing tetrathiafulvalene (TTF) units. We focus mostly on the synthesis of poly- and oligothiophenes with TTF moieties fused to the thiophene units of the conjugated backbone either directly or via a dithiin ring. The electrochemical behaviour of these materials and structure–property relationships are discussed. The study is directed towards the development of a new type of organic semiconductors based on these hybrid materials for application in organic field effect transistors and solar cells.

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“…Such ring fusion increases molecule planarity and enhances orbital overlap, thus maximizing electron delocalization into the organic ligands. Many fused-ring dithiolene systems have been studied, including the fusion of benzene, − functionalized benzene, − thiophene, ,,− pyridine, quinoxaline, , and other heterocyclic systems. − The incorporation of such fused-ring systems allows synthetic modification of the resulting materials via substituents and heteroatoms on the fused-ring units, allowing a great deal of diversity in the resulting dithiolene systems and the potential to finely tune both the electronic structures and solid-state arrangements. In addition, fused benzene analogues containing additional disulfide pairs have also allowed the generation of extended one- and two-dimensional dithiolene-based coordination polymers. , …”

Section: Introductionmentioning

confidence: 99%

Thiophene-Fused Nickel Dithiolenes: A Synthetic Scaffold for Highly Delocalized π-Electron Systems

et al. 2016

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A series of thiophene-fused nickel dithiolene complexes have been prepared via synthetic methods which allow the addition of peripheral aryl groups to the fused thiophene of the dithiolene ligand, thus providing access to a range of structural and electronic modifications to the dithiolene core. X-ray structural studies of the anionic complexes show that the peripheral aryl rings lie in near-perfect coplanarity to the dithiolene core and can form π-stacked columns with N-methylpyridinium cations. Density functional theory calculations show significant delocalization of the frontier orbital electron density into the peripheral aryl rings. The complexes exhibit tunable, intense near-IR (NIR) absorption in the range of 1076-1160 nm with molar absorptivity as high as 25100 M cm in solution. The electronic tunability as well as the desirable solid-state packing arrangements of these systems suggests significant potential as NIR-absorbing materials for optoelectronic applications.

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Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives

Cited by 10 publications

References 33 publications

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

Thiophene-Fused Nickel Dithiolenes: A Synthetic Scaffold for Highly Delocalized π-Electron Systems

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