Abstract The emergence of Y6‐type nonfullerene acceptors has greatly enhanced the power conversion efficiency (PCE) organic solar cells (OSCs). However, which structural feature is responsible for excellent photovoltaic performance still under debate. In this study, two Y6‐like BDOTP‐1 and BDOTP‐2 were designed. Different from previous featuring an A–D–Aʹ–D–A structure, BDOTP‐1, have no electron‐deficient Aʹ fragment in core unit. Instead, there electron‐rich dibenzodioxine core. Although...

A novel and efficient Cu(I)-catalyzed radical heteroannulation reaction of [60]fullerene (C60) with α-bromo acetamides has been disclosed for the direct synthesis diverse C60-fused lactams. Furthermore, formed lactams can be served as a versatile platform further electrochemical functionalization to prepare 1,2-, 1,4-, 1,2,3,16-, 1,4,9,25-adducts C60. In addition, representative fullerene product applied an overcoating layer electron-transporting in n-type perovskite solar cell.

The mechanochemical cascade reaction of [60]fullerene with 3-benzylidene succinimides, diethyl 2-benzylidene succinate, or succinonitrile in the presence an inorganic base has been investigated under solvent-free and ball-milling conditions. This protocol provides expedient method to afford various [60]fullerene-fused cyclopentanes, showing advantages good substrate scope, short time, ambient Furthermore, representative fullerene products have applied inverted planar perovskite solar cells...

Simultaneous electrochemical ring contraction and expansion reactions remain unexplored to date. Herein, the reductive electrosynthesis of heterocycle-fused fulleroids from fullerotetrahydropyridazines electrophiles in presence a trace amount oxygen has been achieved with concurrent expansion. When trifluoroacetic acid alkyl bromides are employed as electrophiles, 1,1,2,6-configuration regioselectively formed. In contrast, 1,1,4,6-configuration produced two separable stereoisomers if...

An unprecedented retro Baeyer–Villiger reaction has been achieved by the electrochemical reduction of [60]fullerene-fused lactones in presence acetic acid at room temperature, affording ketones excellent yields within a short time.

The efficient and regioselective electrosynthesis of tetra- hexa-functionalized [60]fullerene derivatives with unprecedented addition patterns has been achieved. tetra-functionalized derivative an intriguing 1,2,4,17-addition pattern is regioselectively obtained by cyclization reaction the dianionic species generated electrochemically from a [60]fulleroindoline 1,2-bis(bromomethyl)benzene at 0 °C, can be converted to more stable 1,2,3,4-adduct 25 °C. Furthermore, 1,2,3,4,9,10-addition...

Abstract [6,6]-Phenyl-C 61 -butyric acid methyl ester (PCBM), a star molecule in the fullerene field, has found wide applications materials science. Herein, electrosynthesis of buckyballs with fused-ring systems been achieved through radical α-C−H functionalization side-chain for both PCBM and its analogue, [6,6]-phenyl-C -propionic (PCPM), presence trace amount oxygen. Two classes fused bi- tricyclic carbocycles have electrochemically synthesized. Furthermore, an unknown type bisfulleroid...

The development of stable organic dye radicals that exhibit intense and redox-switchable absorption in the short-wavelength infrared (SWIR) region is highly desirable but remains a significant challenge. Herein, we present two neutral nickel(II) radical complexes tetradentate-type azadipyrromethene (ADP), which demonstrate exceptional stability under aerobic conditions high photostability. nature stable, newly synthesized [NiII(ADP.)] was verified through electron paramagnetic resonance...

With the recent advance in chemical modification of fullerenes, electrosynthesis has demonstrated increasing importance regioselective synthesis novel fullerene derivatives. Herein, we report successively stable tetra- and hexafunctionalized [60]fullerene The cycloaddition reaction electrochemically generated dianions from [60]fulleroindolines with phthaloyl chloride regioselectively affords 1,2,4,17-functionalized derivatives two attached ketone groups a unique addition pattern, where...

Self-supervised learning (SSL) has emerged as a crucial technique in image processing, encoding, and understanding, especially for developing today's vision foundation models that utilize large-scale datasets without annotations to enhance various downstream tasks. This study introduces novel SSL approach, Information-Maximized Soft Variable Discretization (IMSVD), representation learning. Specifically, IMSVD softly discretizes each variable the latent space, enabling estimation of their...

The Cu(II)-catalyzed N-heteroannulation reaction of [60]fullerene (C60) with aryl sulfonamides and paraformaldehyde has been disclosed for the synthesis diverse C60-fused imidazolidines, which one or both ArSO2 moieties could be removed selectively. Further transformations into unexpected bicyclic 1,2,3,4-adduct imidazolidinium iodide salt have also demonstrated. A plausible mechanism is proposed on basis control experiments. employed as an additive in PC61BM layer inverted planar perovskite...

Tether-directed electrosynthesis of [60]fullerene derivatives fused with 5-membered azacycle and 13-membered carbocycle, that is, bicyclic 1,4,9,12- 1,2,4,15-adducts, has been achieved unexpectedly for the first time. The novel are obtained by electrochemical reduction [60]fullerene-fused indolines or lactams subsequent regioselective cyclization 2,2″-bis(bromomethyl)-1,1′:3′,1″-terphenyl. product structures have characterized spectroscopic data single-crystal X-ray analysis.

Triflic anhydride (Tf2O) is a potent electrophilic activator for carbonyl groups, facilitating the formation of versatile triflate intermediates that undergo nucleophilic trapping to generate broad array valuable compounds. In this work, we have developed novel method utilizes Tf2O as mediator activation and subsequent intramolecular rearrangement 3,3‐diarylbenzofuranones into anthraquinones 2 anthrones 3. Both are important molecules in fields natural products research, pharmaceuticals,...

Electrochemical benzylation of [60]fullerene-fused lactones with different motifs unexpectedly affords three types ring-opened benzylated adducts under conditions. Both δ- and γ-lactones can be to generate mono- bis-benzylated in good yields. In addition, representative fullerene products have been applied as efficient electron-transport materials perovskite solar cells.

The palladium-catalyzed heteroannulation of [60]fullerene with 4-hydroxycoumarins affords [60]fullerene-fused furochromenones, which can be further derivatized <italic>via</italic> an electrochemical method to synthesize 1,2,3,4-adducts.

Comprehensive Summary A triflic anhydride‐induced annulation of benzoic acids bearing electron‐withdrawing groups with arylalkynes leading to diverse 3‐arylindenones via an unprecedented aryl swapping pathway under air atmosphere and ball‐milling conditions has been disclosed. Most the obtained are fluorine‐containing compounds. The present mechanochemical protocol employs easily available inexpensive acids, which unexpectedly undergo serve as source 3‐aryl group. current methodology shows...

Divergent mechanosynthesis of furanoid-bridged fullerene dimers C 120 O and 2 was achieved from the FeCl 3 -mediated reaction 60 with H under different solvent-free ball-milling conditions.

Abstract Endohedral clusterfullerenes exhibit unique chemical properties due to intramolecular electron transfer of the encaged metal cluster outer fullerene cages. We report synthesis two Sc 3 N@ D h ‐C 78 monoadducts 2 a and b through 1,3‐dipolar reaction with carbonyl ylide bearing anomalous cis ‐conformation regioselectivity. The molecular structures these are unambiguously confirmed by single‐crystal X‐ray crystallography, revealing that both have ‐conformations furan moiety grafted via...

The conversion of the [60]fullerene-fused lactones to ketones with triflic anhydride as an unusual reductant under aerobic conditions has been achieved in excellent yields. present thermal retro Baeyer-Villiger reaction from no precedents. In addition, unique ring-opened peroxy [60]fullerene derivatives can be obtained by electrochemical reactions synthesized ketones.

由于富勒烯衍生物在材料科学和生命科学等领域具有潜在的应用价值,化学家们在过去30年来一直致力于其合成,并且报道了众多功能化富勒烯的合成方法.在这些方法中,电化学合成因其反应条件温和、区域选择性良好和产率相对较高等优点,被认为是制备各种富勒烯衍生物的新颖且高效的策略.电化学还原会导致富勒烯衍生物中杂环结构单元在富勒烯骨架上的碳-杂原子键断裂和重排,为富勒烯衍生物的多官能化提供了新的模式,从而使[60]富勒烯稠合杂环化合物的电化学功能化近年来引起了更为广泛的关注.综述了2011年以来[60]富勒烯稠合杂环化合物的电化学反应研究进展.