About the Unusual Formation of a Vinylogue Tetrathiafulvalene

Richter, A. M.; Bauroth, J.; Fanghänel, E.; Kutschabsky, L.; Radeglia, R.

doi:10.1002/prac.19943360415

Cited by 9 publications

(3 citation statements)

References 7 publications

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“…It should be noted that not only the π-radical cation and dication of the parent TTF (see Table ) but also those of various π - extended TTF derivatives, bearing an additional vinyl group or a furan ring as spacers connecting the two dithiole rings, give rise to a similar blue shift of their corresponding absorptions. , …”

Section: Resultsmentioning

confidence: 99%

Formation and Characterization of the π-Radical Cation and Dication of π-Extended Tetrathiafulvalene Materials

2001

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The π-radical cation as well as the dication species of a series of quinonoid π -extended TTF have been generated by means of time-resolved and steady-state radiation chemical techniques. The spectral characteristics of the π-radical cation revealed fingerprint absorptions, which are predominantly in the red region of the spectrum (570−690 nm). The maxima vary markedly upon altering (i) the substitution pattern of the TTF rings (i.e., H, S−CH3 and S−CH2−CH2−S) and (ii) the different backbone structures (i.e., anthracene, tetracene, and pentacene). In accordance with the electrochemical studies, which give rise to a single two-electron oxidation step forming directly the π -extended TTF dication, the π-radical cation intermediate is short-lived and decays on a time scale of several tens of milliseconds. Clean second-order decay dynamics, indicative for a disproportionation reaction of the π-radical cation into the corresponding dications, govern the instability of the π-radical cation. By contrast the dication species is stable without showing a significant degradation over minutes. All the generated dications show transitions that are significantly shifted to the blue (455−490 nm) relative to the π-radical cation intermediates and are dominated by the polyacenic unit.

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Section: Resultsmentioning

confidence: 99%

Formation and Characterization of the π-Radical Cation and Dication of π-Extended Tetrathiafulvalene Materials

2001

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“…Functional ethylenes and acetylenes containing a readily hydrolysable acetylthio group at the multiple bond are highly reactive synthons and intermediates for fine organic synthesis as well as potential monomers for the preparation of polyethenyl-and polyethynylthiols: redox and complexing polymers which can be used in advanced technologies, in particular, as cathode materials for lithium batteries. [1][2][3] At the same time, the number of such compounds currently known is rather limited, and the methods for their synthesis are, as a rule, multi-stage and time-consuming processes. 4,5 In the present work we studied some new convenient approaches to the synthesis of acetylthioethenes and -ethynes by the reaction of TAA with available chloroethenes and -acetylenes.…”

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confidence: 99%

“…¶ † IR spectra were recorded on a Specord IR-75 spectrometer in a microlayer. 1 H NMR spectra were recorded on a Jeol FX-90 Q instrument (90 MHz) in CDCl 3 , with HMDS as an internal standard. Commercial grade TCE was purified by distillation.…”

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Reaction of thioacetic acid with ethenyl- and ethynyl chlorides

D’yachkova

Beskrylaya

Albanov

et al. 1998

Mendeleev Communications

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ChemInform Abstract: Organic Electronic Conductors and Precursors. Part 16. The Unusual Formation of a Vinylogue Tetrathiafulvalene.

et al. 1994

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Organic Electronic Conductors and Precursors. Part 16. The Unusual Formation of a Vinylogue Tetrathiafulvalene.-Cyclovoltammetric oxidation of (III) gives one potential at 0.55 V. By electrochemical oxidation in CH2Cl2 with Bu4NBF4 as supporting electrolyte small amounts of (V) as the tetrafluoroborate are formed.-(RICHTER, A. M.; BAUROTH, J.; FANGHAENEL, E.; KUTSCHABSKY, L.; RADEGLIA, R.; J. Prakt. Chem./Chem.-Ztg. 336 (1994) 4, 355-356; Dep. Chem., Martin-Luther-Univ.

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About the Unusual Formation of a Vinylogue Tetrathiafulvalene

Cited by 9 publications

References 7 publications

Formation and Characterization of the π-Radical Cation and Dication of π-Extended Tetrathiafulvalene Materials

Formation and Characterization of the π-Radical Cation and Dication of π-Extended Tetrathiafulvalene Materials

Reaction of thioacetic acid with ethenyl- and ethynyl chlorides

ChemInform Abstract: Organic Electronic Conductors and Precursors. Part 16. The Unusual Formation of a Vinylogue Tetrathiafulvalene.

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