Pyridyl‐Endcapped Polyynes: Stabilized Wire‐like Molecules

Krempe, Maximilian; Lippert, Rainer; Hampel, Frank; Jux, Norbert; Tykwinski, Rik R.

doi:10.1002/ange.201608633

Cited by 8 publications

(4 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For oligoynes with n ≥6, additional waves ( E

_{normalC \equiv normalC \to normalC \equiv normalC •^{-}}

)

were also observed due to the reduction of the oligoynes. Although, the redox properties of oligoynes are rarely investigated, a few reports have demonstrated their irreversible electrochemical reduction (Table S6) [5, 6, 12] . While direct comparison is difficult due to the scarcity of data, several compounds based on oligoynes containing six alkyne units were irreversibly reduced at approximately −1.66 V relative to the Fc/Fc + redox couple.…”

Section: Resultsmentioning

confidence: 99%

“…[11] Introducing steric bulk at the 3,5 positions of the pyridyl end‐cap allows for oligoynes 2 to be isolated with up to n =8 [12] . By taking advantage of the pyridyl end‐caps, oligoynes 1 ( n =1, 2, and 4) were anchored onto Au(111) as a molecular wire, [11a,b] while oligoynes 2 ( n =2, 4, and 6) were used to anchor Zn and Ru porphyrin complexes [12] . Oligoyne 2 ( n =6), has also been encapsulated with a phenanthroline‐containing macrocycle to form a rotaxane [13] .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Blending the Optical and Redox Properties of Oligoynes and Boron Difluoride Formazanates

et al. 2022

View full text Add to dashboard Cite

Oligoynes and polyynes are 1D chains of conjugated sp-hybridized carbon atoms consisting of alternating single and triple bonds. Their stability rapidly decreases with increasing chain length beyond only a few repeating units. Design strategies, such as the use of bulky end-capping groups, allow for their characterization and isolation while not contributing significantly to their physical properties. In this study, we incorporate redox-active BF 2 formazanate dyes (BF 2 ) as end-caps to prepare symmetric (BF 2 À [C�C] n À BF 2 ) and asymmetric (BF 2 À [C�C] n À Si(iPr) 3 ) families of oligoynes containing up to 10 alkyne units. In doing so, we introduce stable oligoynes that possess a blend of optical and redox properties that cannot be achieved by either oligoynes or BF 2 formazanates individually (e.g., panchromatic absorption, multiple and tunable reversible redox waves). This approach is transferable to other functional end-caps to facilitate the preparation of π-conjugated materials with utility in the organic electronics arena.

show abstract

“…For oligoynes with n ≥6, additional waves ( E

_{normalC \equiv normalC \to normalC \equiv normalC •^{-}}

)

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Blending the Optical and Redox Properties of Oligoynes and Boron Difluoride Formazanates

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Short polyyne can be stabilized by using hydrogen as terminations on both ends [ 3 , 4 , 5 , 6 ]. Larger chemical ending groups should be applied for longer polyynes to hinder their reactivity [ 7 , 8 , 9 , 10 ]. However, cross-linking reactions between the polyyne molecules are unavoidable, making it difficult to synthesize long polyynes.…”

Section: Introductionmentioning

confidence: 99%

Encapsulation and Evolution of Polyynes Inside Single-Walled Carbon Nanotubes

Tang,

Li,

Chen

et al. 2024

Nanomaterials

View full text Add to dashboard Cite

Polyyne is an sp-hybridized linear carbon chain (LCC) with alternating single and triple carbon–carbon bonds. Polyyne is very reactive; thus, its structure can be easily damaged through a cross-linking reaction between the molecules. The longer the polyyne is, the more unstable it becomes. Therefore, it is difficult to directly synthesize long polyynes in a solvent. The encapsulation of polyynes inside carbon nanotubes not only stabilizes the molecules to avoid cross-linking reactions, but also allows a restriction reaction to occur solely at the ends of the polyynes, resulting in long LCCs. Here, by controlling the diameter of single-walled carbon nanotubes (SWCNTs), polyynes were filled with high yield below room temperature. Subsequent annealing of the filled samples promoted the reaction between the polyynes, leading to the formation of long LCCs. More importantly, single chiral (6,5) SWCNTs with high purity were used for the successful encapsulation of polyynes for the first time, and LCCs were synthesized by coalescing the polyynes in the (6,5) SWCNTs. This method holds promise for further exploration of the synthesis of property-tailored LCCs through encapsulation inside different chiral SWCNTs.

show abstract

“…Pyridyl end‐capped oligoynes 1 can be isolated up to n =4, where n denotes the number of C≡C bonds (Figure 1). [11] Introducing steric bulk at the 3,5 positions of the pyridyl end‐cap allows for oligoynes 2 to be isolated with up to n =8 [12] . By taking advantage of the pyridyl end‐caps, oligoynes 1 ( n =1, 2, and 4) were anchored onto Au(111) as a molecular wire, [11a,b] while oligoynes 2 ( n =2, 4, and 6) were used to anchor Zn and Ru porphyrin complexes [12] .…”

Section: Introductionmentioning

confidence: 99%