A Tetrathiafulvalene‐Functionalized Radiaannulene with Multiple Redox States

Lincke, Kasper; Frellsen, Anders Floor; Parker, Christian R.; Bond, Andrew D.; Hammerich, Ole; Nielsen, Mogens Brøndsted

doi:10.1002/anie.201202324

Cited by 35 publications

(36 citation statements)

References 33 publications

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“…For radiaannulene 2a we previously found a longest-wavelength absorption of 644 nm (ε 11000 M −1 cm −1 ) [10]. We assign these low-energy bands to charge-transfer absorptions, which are usually observed in π-conjugated systems containing TTF donors and large acetylenic scaffolds that behave as electron acceptors [8–10].…”

Section: Resultsmentioning

confidence: 86%

“…For the radiaannulene 2a removal of two electrons was previously [10] found to occur stepwise with a separation between the first and second oxidations of 90 mV. Thus, despite the long gem- TEE bridging units, there is a weak interaction between the TTFs that are separated by a shortest distance of 6.64 Å according to the X-ray crystal structure [10]. For the other radiaannulene, 8 , the first oxidation of each TTF unit was also split into two waves, again indicating interaction between them.…”

Section: Resultsmentioning

confidence: 99%

“…The NIR absorptions of 4 •+ and 8 •+ disappeared upon further oxidation to the dications, corroborating the CT character. The position of the more well-defined NIR absorption band of 8 •+ is close to that of 2a •+ at 2257 nm [10]; 2b •+ also experiences this absorption according to the EPR-spectroelectrochemistry described above (see Fig. 8), but in that experiment, the NIR detection only goes to 2000 nm and therefore does not provide the full NIR absorption band.…”

Section: Resultsmentioning

confidence: 99%

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Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

Jiang¹,

Mazzanti

Parker³

et al. 2015

Beilstein J. Org. Chem.

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SummaryA selection of cyclic and acyclic acetylenic scaffolds bearing two tetrathiafulvalene (TTF) units was prepared by different metal-catalyzed coupling reactions. The bridge separating the two TTF units was systematically changed from linearly conjugated ethyne, butadiyne and tetraethynylethene (trans-substituted) units to a cross-conjugated tetraethynylethene unit, placed in either acyclic or cyclic arrangements. The cyclic structures correspond to so-called radiaannulenes having both endo- and exocyclic double bonds. Interactions between two redox-active TTF units in these molecules were investigated by cyclic voltammetry, UV–vis–NIR and EPR absorption spectroscopical methods of the electrochemically generated oxidized species. The electron-accepting properties of the acetylenic cores were also investigated electrochemically.

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Section: Resultsmentioning

confidence: 86%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

Jiang¹,

Mazzanti

Parker³

et al. 2015

Beilstein J. Org. Chem.

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“…Nielsen and co-workers synthesized TTF coupled radiaannulene derivative (OAm2, Scheme 3). [39] This molecule shows the electrochemically accessible six-redox states with two reduced states, one neutral state and three oxidized states (À 2/À 1/0/ + 1/ + 2/ + 4). The CV results demonstrated three oxidation waves and two reduction waves.…”

Section: Ambipolar Moleculesmentioning

confidence: 99%

“…Radiaannulenes are cyclic molecules, which have endo and exocyclic double bonds and consequently lie between radialenes and annulenes. Nielsen and co‐workers synthesized TTF coupled radiaannulene derivative ( OAm2 , Scheme ) . This molecule shows the electrochemically accessible six‐redox states with two reduced states, one neutral state and three oxidized states (−2/−1/0/+1/+2/+4).…”

Section: Classification Of Multiredox Systemsmentioning

confidence: 99%

Molecular and Supramolecular Multiredox Systems

2020

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The design and synthesis of molecular and supramolecular multiredox systems have been summarized. These systems are of great importance as they can be employed in the next generation of materials for energy storage, energy transport, and solar fuel production. Nature provides guiding pathways and insights to judiciously incorporate and tune the various molecular and supramolecular design aspects that result in the formation of complex and efficient systems. In this review, we have classified molecular multiredox systems into organic and organic‐inorganic hybrid systems. The organic multiredox systems are further classified into multielectron acceptors, multielectron donors and ambipolar molecules. Synthetic chemists have integrated different electron donating and electron withdrawing groups to realize these complex molecular systems. Further, we have reviewed supramolecular multiredox systems, redox‐active host‐guest recognition, including mechanically interlocked systems. Finally, the review provides a discussion on the diverse applications, e. g. in artificial photosynthesis, water splitting, dynamic random access memory, etc. that can be realized from these artificial molecular or supramolecular multiredox systems.

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Organic Building Blocks for Molecular Engineering

Lincke¹,

Nielsen²

2013

Organic Synthesis and Molecular Engineering

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A Tetrathiafulvalene‐Functionalized Radiaannulene with Multiple Redox States

Cited by 35 publications

References 33 publications

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

Molecular and Supramolecular Multiredox Systems

Organic Building Blocks for Molecular Engineering

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