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Reversible Quinoid-Diradical Inter-conversion in Single-Molecule Junctions.
IF 3.9 2区 化学
Chemistry - A European Journal Pub Date : 2025-03-31 DOI: 10.1002/chem.202500921
Ming Chen, Yunjiao Peng, Junrui Zhang, Wei Liu, Xunshan Liu
{"title":"Reversible Quinoid-Diradical Inter-conversion in Single-Molecule Junctions.","authors":"Ming Chen, Yunjiao Peng, Junrui Zhang, Wei Liu, Xunshan Liu","doi":"10.1002/chem.202500921","DOIUrl":"https://doi.org/10.1002/chem.202500921","url":null,"abstract":"<p><p>profound understanding of the reversible regulation mechanisms among multiple redox states of organic molecules is essential for further development of molecular switching devices. In this study, an oligo-aniline derived quinoidal molecular wire was designed and synthesized. The reversible inter-conversion processes between its initial (quinoidal) and protonated (diradical) states were comprehensively investigated with optical measurements, and the EPR experiments confirmed the formation of radical species upon protonation. The single-molecule charge transport properties were then investigated using scanning tunneling microscopy break junction (STM-BJ) technique. It was found that the molecular wire O-ANI can serve as a reversible molecular switching process with around 6.5-fold conductance variation through acid/base adjustments. Additionally, theoretical analyses elucidated the mechanism of the quinoidal-diradical inter-conversion. The enhanced comprehension of the reversible quinoidal-diradical inter-conversion at the single-molecule level provides new strategies for advancing the molecular switching materials and devices.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202500921"},"PeriodicalIF":3.9,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750619","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Control of Chemo-Selectivity via Alcohol Affected Kinetics in Cu-Hydroxylamine Catalyzed Aerobic Oxidation of Mesitol.
IF 3.9 2区 化学
Chemistry - A European Journal Pub Date : 2025-03-31 DOI: 10.1002/chem.202501032
Jiaxin Liu, Yongtao Wang, Jia Yao, Haoran Li
{"title":"Control of Chemo-Selectivity via Alcohol Affected Kinetics in Cu-Hydroxylamine Catalyzed Aerobic Oxidation of Mesitol.","authors":"Jiaxin Liu, Yongtao Wang, Jia Yao, Haoran Li","doi":"10.1002/chem.202501032","DOIUrl":"https://doi.org/10.1002/chem.202501032","url":null,"abstract":"<p><p>Chemo-selectivity control is a critical challenge in aerobic C-H oxidations, particularly in preventing overoxidation. In this work, we present an alcohol-tunable strategy to control the oxidation degree of CuCl2/NH2OH·HCl-catalyzed mesitol oxidation in alcohols. In tBuOH, the reaction efficiently yields the aldehyde product with high selectivity, whereas in MeOH, the ether intermediate turned to be the predominant product. Further kinetic analysis and mechanistic studies revealed that the reactivity is driven by the in-situ formation of protonated alkyl nitrate ([RON(O)OH]+), highlighting the critical role of ROH solvents. The differing responses of mesitol and the ether intermediate to the reaction conditions result in distinct kinetics across different alcohols, enabling precise control over the final products. These findings provide mechanistic insights into the origins of alcohol-dependent chemo-selectivity and pave the way for advancing protocols for selectivity control.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202501032"},"PeriodicalIF":3.9,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750472","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Molecular Rectangles Featuring Two Parallel NCN-Coordinated Platinum Units: Enhancing Near-infrared Emission through Excimer Formation.
IF 3.9 2区 化学
Chemistry - A European Journal Pub Date : 2025-03-31 DOI: 10.1002/chem.202500834
Rebecca Salthouse, Amit Sil, Piotr Pander, Fernando Dias, J A Gareth Williams
{"title":"Molecular Rectangles Featuring Two Parallel NCN-Coordinated Platinum Units: Enhancing Near-infrared Emission through Excimer Formation.","authors":"Rebecca Salthouse, Amit Sil, Piotr Pander, Fernando Dias, J A Gareth Williams","doi":"10.1002/chem.202500834","DOIUrl":"https://doi.org/10.1002/chem.202500834","url":null,"abstract":"<p><p>New macrocyclic molecules are described that incorporate Pt(NCN) units on opposite edges of a rectangular structure, with xanthene units constituting the other two sides.  Here, NCN represents a cyclometallating tridentate ligand based on 2,6-di(2-pyridyl)benzene or its pyrimidine analogue.  The complexes display strong photoluminescence peaking in the near-infrared region of the spectrum in solution (λmax up to 761 nm).  Photophysical data and DFT calculations indicate that the emission arises from \"intramolecular excimers\" - triplet excited states that form when the two Pt(NCN) units within the molecule are brought into close proximity to interact interfacially.  In doped polymers, the necessary molecular distortion is inhibited, but related excited states that emit in a similar region can still form through intermolecular interactions.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202500834"},"PeriodicalIF":3.9,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750616","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Photochromic Dysprosium Compound Supported by β-diketone Dithienylethene Ligand.
IF 3.9 2区 化学
Chemistry - A European Journal Pub Date : 2025-03-31 DOI: 10.1002/chem.202500527
Quan Zhou, Zhenhua Zhu, Xu Ying, Xiao-Lei Li, Jinkui Tang
{"title":"A Photochromic Dysprosium Compound Supported by β-diketone Dithienylethene Ligand.","authors":"Quan Zhou, Zhenhua Zhu, Xu Ying, Xiao-Lei Li, Jinkui Tang","doi":"10.1002/chem.202500527","DOIUrl":"https://doi.org/10.1002/chem.202500527","url":null,"abstract":"<p><p>Air-stable lanthanide single-molecule magnets (SMMs) with photochromic units, e.g. dithienylethene (DTE), anthracene and polyoxometalates (POMs), have attracted considerable attentions in the field of molecular magnetism as they could increase the range of applications of magnetic molecules. However, the number of photochromic lanthanide SMMs is scarce. Inspired by a boron-based molecule featuring near-infrared absorption supported by a DTE-containing β-diketonate ligand (3ThacacH) reported by Vivian Wing-Wah Yam et al., in this work, we employed this ligand to lanthanide systems for the first time constructing an air-stable mononuclear Dy(III)-based compound, Dy(o-3Thacac)3phen. It is a typical zero-field SMM with the anisotropy barrier approaching 100 K. Its reversible photochromic behaviors in solution were determined by UV-Vis absorption and 1H NMR spectra. The inevitable byproducts upon UV irradiation combined with the low yield of photocyclization reaction lead to the incomplete photochromism in solid state. However, distinct relaxation rates of quantum tunneling of the magnetization between Dy(o-3Thacac)3phen and the irradiated sample were observed, demonstrating the feasibility of using 3ThacacH to modulate magnetodynamics. Meanwhile, this work highlights the vital roles of avoiding photoinduced byproducts, achieving photochromic single-crystal-to-single-crystal transformation and high yields of photocyclization / photocycloreversion reaction in elucidating the photo-responsive relaxation mechanism and future device applications.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202500527"},"PeriodicalIF":3.9,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750445","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
CuH-Catalyzed Regio- and Enantioselective Hydroallylation of 1-Trifluoromethylthioalkenes: Leaving Group-Dependent Stereochemistry.
IF 3.9 2区 化学
Chemistry - A European Journal Pub Date : 2025-03-31 DOI: 10.1002/chem.202501210
Yuki Kojima, Shinichi Suda, Wataru Kanna, Yuji Nishii, Satoshi Maeda, Koji Hirano
{"title":"CuH-Catalyzed Regio- and Enantioselective Hydroallylation of 1-Trifluoromethylthioalkenes: Leaving Group-Dependent Stereochemistry.","authors":"Yuki Kojima, Shinichi Suda, Wataru Kanna, Yuji Nishii, Satoshi Maeda, Koji Hirano","doi":"10.1002/chem.202501210","DOIUrl":"https://doi.org/10.1002/chem.202501210","url":null,"abstract":"<p><p>A copper-catalyzed regio- and enantioselective hydroallylation of 1-trifluoromethylthioalkenes with hydrosilanes and allylic electrophiles has been developed. The judicious choice of chiral ligands successfully promotes the enantioselective C(sp3)-C(sp3) bond formation at the α-position of trifluoromethylthio (SCF3) group, which is otherwise difficult to perform by other means. Experimental and computational mechanistic studies reveal that leaving groups of allylic electrophiles significantly influence the enantioselectivity as well as chemoselectivity.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202501210"},"PeriodicalIF":3.9,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750480","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Fluorescent Carbazole-derived Aza[5]helicenes: Synthesis, Functionalization, and Characterization.
IF 3.9 2区 化学
Chemistry - A European Journal Pub Date : 2025-03-31 DOI: 10.1002/chem.202501081
Inka Marten, Melina E A Dilanas, Joachim Podlech
{"title":"Fluorescent Carbazole-derived Aza[5]helicenes: Synthesis, Functionalization, and Characterization.","authors":"Inka Marten, Melina E A Dilanas, Joachim Podlech","doi":"10.1002/chem.202501081","DOIUrl":"https://doi.org/10.1002/chem.202501081","url":null,"abstract":"<p><p>5,8-Dihydroindolo[2,3-c]carbazole (ICz), 9H-cinnolino[3,4-c]carbazole (CnCz), and variously alkyl-, alkenyl-, and aryl-substituted indolo[2,3-k]- and -[3,2-a]phenanthridines (IPs) were synthesized using an ortho fusion strategy with Suzuki cross couplings, intramolecular nitrene insertions, diazo couplings, and Morgan-Walls cyclizations as key reactions. The IPs were additionally transformed into organoboranes and helicene conjugates with tetraphenylethylene derivatives. The compounds fluoresce with large Stokes shifts, exhibit strong acidochromism, and show a good to excellent aggregation-induced emission. Their helical structure was elucidated by X-ray crystallographic analysis and by quantum chemical calculations. HOMO-LUMO gaps of 3.96-4.06 eV and S1-T1 gaps were calculated with CnCz showing a small singlet-triplet inversion. Relative pKa values of 6.65-9.55 were estimated for the different types of azahelicenes.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202501081"},"PeriodicalIF":3.9,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750557","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Total Synthesis of (-)-Vescalagin, the Iconic Member of the C-Glucosidic Ellagitannin Family.
IF 3.9 2区 化学
Chemistry - A European Journal Pub Date : 2025-03-31 DOI: 10.1002/chem.202501159
Romain Larrieu, Anaëlle Cornu, Laurent Pouységu, Denis Deffieux, Stéphane Quideau
{"title":"Total Synthesis of (-)-Vescalagin, the Iconic Member of the C-Glucosidic Ellagitannin Family.","authors":"Romain Larrieu, Anaëlle Cornu, Laurent Pouységu, Denis Deffieux, Stéphane Quideau","doi":"10.1002/chem.202501159","DOIUrl":"https://doi.org/10.1002/chem.202501159","url":null,"abstract":"<p><p>The first total synthesis of the 2,3,5-O-(S,R)-NonaHydroxyTriPhenoylated (NHTP) and 4,6-O-(S)-HexaHydroxy-DiPhenoylated (HHDP) C-glucosidic ellagitannin (-)-vescalagin was accomplished through a bioinspired route involving intramolecular atroposelective cupric-diamine complex-mediated phenolic couplings of gallates to forge its HHDP and NHTP units, and a methoxyamine-driven opening of a glucopyranose intermediate followed by a phenolic aldol-type reaction to form its C-arylglucosidic bond. The minor epimer that resulted from this bond-forming event was used to complete also a first total synthesis of the vescalagin epimer, (-)-castalagin.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202501159"},"PeriodicalIF":3.9,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750587","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
The Careful Combination of Bismuth Compounds and CAAC: Formal Halonium and Nitrenium Transfer via Radical Pathways.
IF 3.9 2区 化学
Chemistry - A European Journal Pub Date : 2025-03-31 DOI: 10.1002/chem.202500913
Gargi Kundu, Ahmed Fetoh, Jordi Poater, Crispin Lichtenberg
{"title":"The Careful Combination of Bismuth Compounds and CAAC: Formal Halonium and Nitrenium Transfer via Radical Pathways.","authors":"Gargi Kundu, Ahmed Fetoh, Jordi Poater, Crispin Lichtenberg","doi":"10.1002/chem.202500913","DOIUrl":"https://doi.org/10.1002/chem.202500913","url":null,"abstract":"<p><p>Cyclic (alkyl)(amino)carbenes (CAACs) are key compounds en route to a plethora of unprecedented low-valent and radical complexes of transition metals and main group elements. For p-block elements of the 6th period, however, low-valent and radical complexes of CAACs are extremely rare, and even simple adducts with CAACs are difficult to access. Here we report the full characterization of the first adduct between a CAAC and a bismuth trihalide, [BiCl3(Me2CAAC)] (1), which has previously only been spectroscopically characterized. 1 and its in situ generated bromido analog form intensely colored solutions in THF and undergo formal halonium ion (i.e. X+) transfer from the Bi atom to the carbene carbon atom to give the complex cations [CAAC-X]+ (X = Cl, Br). Starting from bismuth amide complexes, formal nitrenium ion (i.e. [NR2]+) transfer reactions are observed to give [CAAC-NR2]+. EPR spectroscopic reaction monitoring indicates the viability of radical processes and suggests the involvement of unprecedented α-aminyl radicals and mononuclear Bi0 species. Our investigations reveal easily accessible radical pathways via peerless molecular complexes, which proceed in the absence of external reducing agents, as a key factor on the way to exploit the full potential of carbene ligands in the chemistry of sixth row p-block elements.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202500913"},"PeriodicalIF":3.9,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750633","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Highly Emissive Flexible Organic Crystals with Broad Piezochromism and Optical Waveguide s.
IF 3.9 2区 化学
Chemistry - A European Journal Pub Date : 2025-03-31 DOI: 10.1002/chem.202500888
Yaya Li, Huixu Yang, Yanan Wang, Chunyan Lv, Chengjian Li, Kai Wang, Yujian Zhang
{"title":"Highly Emissive Flexible Organic Crystals with Broad Piezochromism and Optical Waveguide s.","authors":"Yaya Li, Huixu Yang, Yanan Wang, Chunyan Lv, Chengjian Li, Kai Wang, Yujian Zhang","doi":"10.1002/chem.202500888","DOIUrl":"https://doi.org/10.1002/chem.202500888","url":null,"abstract":"<p><p>The integration of mechanical flexibility with stimuli-responsive optical properties in organic single crystals (OSCs) remains a formidable challenge due to the intrinsic rigidity of π-conjugated systems. Herein, we report a rationally designed OSC, FBCF, that synergistically combines elastic deformability, broad piezochromism and low-loss optical waveguiding via a planar benzothiadiazole (BTA) core and fluoroarene termini. The molecular architecture enforces face-to-face slip-stacking via multiple noncovalent interactions (N···H, π-π, and C-F···π), yielding centimeter-scale crystals with exceptional elastic bending and full recovery. These crystals exhibit a high photoluminescence (PL) efficiency (PLQY = 75.8%) and serve as low-loss optical waveguides, maintaining performance even when bent (optical loss coefficients: 0.286-0.529 dB mm-1). Crucially, FBCF exhibits broad pressure-responsive spectral shifts (Δλ = 171 nm), achieving a piezochromic sensitivity of 16.7 nmGPa-1, exceeding that of most organic systems. Single-crystal X-ray diffraction analyses reveal hierarchical packing: rigid lamellar layers (stabilized by strong π-π/dipole interactions, ‑118.56 to ‑58.45 kcal/mol) interconnected via weaker interlayer C-F···π bonds (-18.8 kcal/mol). This architecture enables elastic deformation through interlayer slippage while preserving intralayer order.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202500888"},"PeriodicalIF":3.9,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750602","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Self-Sensitized Fulgimides with Selective Multiplicity-Based Three-State Photoswitching.
IF 3.9 2区 化学
Chemistry - A European Journal Pub Date : 2025-03-31 DOI: 10.1002/chem.202500678
Jakub Copko, Lucie Ludvíková, Tomáš Slanina
{"title":"Self-Sensitized Fulgimides with Selective Multiplicity-Based Three-State Photoswitching.","authors":"Jakub Copko, Lucie Ludvíková, Tomáš Slanina","doi":"10.1002/chem.202500678","DOIUrl":"https://doi.org/10.1002/chem.202500678","url":null,"abstract":"<p><p>Precise control over excited-state multiplicity is a powerful strategy for controlling photochemical reactivity, particularly in multimodal systems where different multiplicities lead to distinct reaction products. Here, we present a multiplicity-sensitive, multimodal, fulgimide-based system capable of three-state photoswitching both in solution and in solid state. With the aim of suppressing singlet-state sensitization, we rationally designed an intramolecularly sensitized system that enables triplet-exclusive energy transfer - a crucial feature for selective multiplicity-dependent reactivity. Our findings provide insights into the underlying principles of intramolecular triplet-exclusive sensitization and its application in controlling three-state photoswitching in unimolecular systems.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202500678"},"PeriodicalIF":3.9,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750622","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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