Nucleophilic trifluoromethylation of azinium salts with Zn(CF3)2·bpy

Pan, Shitao; Wang, Xiu; Ni, Chuanfa; Hu, Jinbo

doi:10.1016/j.tet.2021.132477

Cited by 4 publications

(4 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is known that CF3SOOions can generate SO2 and in presence of heat, acids, or bases, 25, where SO2 is a good reducing agent for the iodine and triiodide reduction. 25,26 Previous studies have shown that molecular iodine generation in perovskites under illumination is a common phenomenon and can accelerate the degradation of perovskites 17 We thus hypothesize that CF3SOOions can reduce I2 into in the perovskite solutions. 17 To verify it, we added Zn(OOSCF3)2 into the iodine solution with a molar ratio of 1:1, and observed that iodine color started to shifting from dark brown to transparent (Fig.…”

Section: Function Of Cations and Anions Of Zn(ooscf3)2mentioning

confidence: 84%

Iodide Manipulation Using Zinc Additives for Efficient Perovskite Solar Minimodules

Huang

Uddin

Rana

et al. 2023

Preprint

View full text Add to dashboard Cite

Interstitial iodides are the most important type of defects in perovskite solar cells that limits efficiency and stability. They can be generated during solution, film, and device processing and further accelerate device degradation. Herein, we find that introducing a small amount of an organozinc compound- zinc trifluoromethanesulfinate (Zn(OOSCF3)2) in the perovskite solution can control the iodide defects in resultant perovskites ink and films. CF3SOŌ vigorously suppresses molecular iodine formation in the perovskites by reducing it to iodide, while zinc cations can precipitate out excess iodide by forming a Zn-Amine complex so that the iodide interstitials in the resultant perovskite films can be suppressed. The perovskite films using these additives show improved photoluminescence quantum efficiency and reduce deep trap density, despite that zinc cations reduce the perovskite grain size and iodide interstitials. The zinc additives facilitate the formation of more uniform perovskite films on large-area substrates (78-108 cm2) in the blade-coating process. Fabricated minimodules show power conversion efficiencies of 19.60% and 19.21% with aperture areas of 84 and 108 cm2, respectively, as certified by National Renewable Energy Laboratory (NREL), the highest efficiency certified for minimodules of these sizes.

show abstract

Section: Function Of Cations and Anions Of Zn(ooscf3)2mentioning

confidence: 84%

Iodide Manipulation Using Zinc Additives for Efficient Perovskite Solar Minimodules

Huang

Uddin

Rana

et al. 2023

Preprint

View full text Add to dashboard Cite

show abstract

“…It is known that CF 3 SOO ‒ ions can generate SO 2 and CF 3 ‒ in the presence of heat, acids, or bases 25 , where SO 2 is a good reducing agent for iodine and triiodide reduction 28 , 29 . Gibbs free energy of the redox process between SO 2 and I 2 is ca .…”

Section: Resultsmentioning

confidence: 99%

Iodide manipulation using zinc additives for efficient perovskite solar minimodules

Uddin,

Rana,

et al. 2024

Nat Commun

View full text Add to dashboard Cite

Interstitial iodides are the most critical type of defects in perovskite solar cells that limits efficiency and stability. They can be generated during solution, film, and device processing, further accelerating degradation. Herein, we find that introducing a small amount of a zinc salt- zinc trifluoromethane sulfonate (Zn(OOSCF3)2) in the perovskite solution can control the iodide defects in resultant perovskites ink and films. CF3SOO̶ vigorously suppresses molecular iodine formation in the perovskites by reducing it to iodide. At the same time, zinc cations can precipitate excess iodide by forming a Zn-Amine complex so that the iodide interstitials in the resultant perovskite films can be suppressed. The perovskite films using these additives show improved photoluminescence quantum efficiency and reduce deep trap density, despite zinc cations reducing the perovskite grain size and iodide interstitials. The zinc additives facilitate the formation of more uniform perovskite films on large-area substrates (78-108 cm2) in the blade-coating process. Fabricated minimodules show power conversion efficiencies of 19.60% and 19.21% with aperture areas of 84 and 108 cm2, respectively, as certified by National Renewable Energy Laboratory (NREL), the highest efficiency certified for minimodules of these sizes.

show abstract

“…Trifluoromethyl groups are widespread in pharmaceuticals and agrochemicals, and the formation of organic trifluoromethyl compounds often utilize trifluoromethyl–metal complexes as CF 3 sources. ,− In this regard, trifluoromethyl zinc complexes have been employed for the trifluoromethylation of azinium salts, aromatic compounds, , alkynes, alkenes, carboxamides, sulfonamides, cycloalkanone oximes, and arylcyclopropanes. , …”

Section: Resultsmentioning

confidence: 99%

Organozinc Fluoride and Trifluoromethyl Compounds Supported by the Bis(2-pyridylthio)methyl Ligand

Shlian

Parkin

2022

Organometallics

View full text Add to dashboard Cite

The bis(2-pyridylthio)methyl ligand, [Bptm], has been employed in the synthesis of {[Bptm]Zn(μ-F)} 2 , a rare example of an organozinc fluoride compound. The dimeric nature of {[Bptm]Zn(μ-F)} 2 , which possesses an uncommon [Zn(μ-F)] 2 motif, contrasts with the monomeric structures reported for the other halide derivatives, [Bptm]ZnX (X = Cl, Br, I); this difference is supported by density functional theory calculations which indicate that the fluoride derivative favors a dimeric form with bridging fluoride ligands, whereas the other derivatives favor monomeric structures with terminal halide ligands. {[Bptm]Zn(μ-F)} 2 reacts with Me 3 SiCF 3 to afford the organozinc trifluoromethyl complex, namely [Bptm]ZnCF 3 . The Zn−CF 3 bond in this complex is longer than the Zn−CH 3 bond of the previously reported methyl derivative [Bptm]ZnMe, an observation that is precedented in related zinc compounds but counter to other metal complexes. The infrared frequency corresponding to the asymmetric C−F stretch of [Bptm]ZnCF 3 is unusually low for a metal trifluoromethyl species but is comparable to those for other zinc and cadmium complexes.

show abstract

Nucleophilic trifluoromethylation of azinium salts with Zn(CF3)2·bpy

Cited by 4 publications

References 43 publications

Iodide Manipulation Using Zinc Additives for Efficient Perovskite Solar Minimodules

Iodide Manipulation Using Zinc Additives for Efficient Perovskite Solar Minimodules

Iodide manipulation using zinc additives for efficient perovskite solar minimodules

Organozinc Fluoride and Trifluoromethyl Compounds Supported by the Bis(2-pyridylthio)methyl Ligand

Contact Info

Product

Resources

About