共查询到20条相似文献,搜索用时 0 毫秒
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Dr. Lenka Pallova Dr. Etienne S. Gauthier Dr. Laura Abella Marion Jean Dr. Nicolas Vanthuyne Dr. Vincent Dorcet Dr. Laure Vendier Prof. Jochen Autschbach Dr. Jeanne Crassous Dr. Stéphanie Bastin Dr. Vincent César 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(28):7722-7730
The straightforward, multigram-scale synthesis of the partially saturated H6-fluoreno[n]helicenes (n=5 or 7) featuring a central, overcrowded alkene is described. The key cyclization step was based on an intramolecular McMurry reaction from the corresponding 1,5-diketones. Chiral stationary phase HPLC analysis and isomer separation indicate that each helicenic compound is constituted of three diastereoisomers at room temperature, i. e. the configurationally stable (R,R,P)/(S,S,M) pair of enantiomers and an apparently achiral compound resulting from the rapid interconversion between the (R,S,P) and (S,R,M) enantiomers. The partially saturated H6-fluoreno[n]helicenes are oxidatively aromatized to give an efficient access to the corresponding fluoreno[n]helicenes. The chiroptical properties (vibrational and electronic circular dichroism) of the chiral, enantiopure compounds have been measured and analyzed by quantum-chemical calculations, confirming their helicoidal nature. 相似文献
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Min Yan Qiang Zhou Prof. Dr. Ping Lu 《Angewandte Chemie (International ed. in English)》2023,62(7):e202218008
Cyclobutenones provide a straightforward four-carbon ring platform for further structural elaborations in that every carbon atom of the ring could be potentially functionalized. We report here a nickel catalyzed enantioconvergent Negishi coupling of 4-iodocyclobutenones with an array of aryl or alkenyl zinc reagents to access enantioenriched 4-substituted cyclobutenones, from which a modular approach to the synthesis of 1,2,3,4-tetrasubstituted cyclobutanes was demonstrated. 相似文献
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Smith BB Hill DE Cropp TA Walsh RD Cartrette D Hipps S Shachter AM Pennington WT Kwochka WR 《The Journal of organic chemistry》2002,67(15):5333-5337
Reaction of the bis-9-BBN adduct of several dienes with 1,3-dibromobenzene via Suzuki coupling leads to a series of [n]metacyclophanes ranging in size from 10 to 17 atom members. In each case, two carbon-carbon bonds are formed in one reaction vessel. However, when the bis-9-BBN adduct of 1,5-hexadiene is coupled with a variety of aryl dihalides, larger [n.n]cyclophanes were formed in preference to the [n]cyclophanes. Four carbon-carbon bonds are formed in this instance. Single-crystal X-ray analyses of these [n.n]cyclophanes reveal interestingly shaped molecules with large cavities. 相似文献
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Regioselective Synthesis and Characterization of Multinuclear Convex‐Bound Ruthenium‐[n]Cycloparaphenylene (n=5 and 6) Complexes 下载免费PDF全文
Dr. Eiichi Kayahara Dr. Vijay Kumar Patel Audrey Mercier Prof. Dr. E. Peter Kündig Prof. Dr. Shigeru Yamago 《Angewandte Chemie (International ed. in English)》2016,55(1):302-306
Mono‐ and multinuclear complexes of ruthenium and [n]cycloparaphenylene (CPP, n=5 and 6) were synthesized in excellent yields through ligand exchange of the cationic complex [(Cp)Ru(CH3CN)3](PF6) with CPP. In the multinuclear complexes, ruthenium selectively coordinated to alternate paraphenylene units to give bis‐ and tris‐coordinated Ru complexes for [5] and [6]CPPs, respectively. Single‐crystal X‐ray analysis revealed the Ru was coordinated with η6‐hapticity on the convex surface of CPP. 相似文献
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Terri C. Lovell Zachary R. Garrison Prof. Dr. Ramesh Jasti 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(34):14469-14473
Conjugated aromatic macrocycles are attractive due to their unique photophysical and optoelectronic properties. In particular, the cyclic radially oriented π-system of cycloparaphenylenes (CPPs) gives rise to photophysical properties unlike any other small molecule or carbon nanomaterial. CPPs have tunable emission, possess large extinction coefficients, wide effective Stokes shifts, and high quantum yields. However, accessing bright CPPs with emissions beyond 500 nm remains difficult. Herein, we present a novel and bright orange-emitting CPP-based fluorophore showing a dramatic 105 nm red-shift in emission and striking 237 nm effective Stokes shift while retaining a large quantum yield of 0.59. We postulate, and experimentally and theoretically support, that the quantum yield remains large due to the lack of intramolecular charge transfer. 相似文献
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Flow‐Assisted Synthesis of [10]Cycloparaphenylene through Serial Microreactions under Mild Conditions 下载免费PDF全文
Dr. Heejin Kim Hyune‐Jea Lee Prof. Dr. Dong‐Pyo Kim 《Angewandte Chemie (International ed. in English)》2016,55(4):1422-1426
Cycloparaphenylene (CPP) has been recognized as an attractive template for the bottom‐up synthesis of carbon nanotubes with uniform diameter, and is important for the chemistry of graphitic as well as ring‐shaped macromolecules. However, the reported routes from halogenated benzenes have suffered from low yields even under time‐ and labor‐consuming multistep conditions. Herein we report a flow‐assisted synthesis of [10]CPP in four steps under mild conditions. For the synthesis, a selective nucleophilic addition of the unprotected diketone without the double‐added byproduct was achieved within 3 s in high yield. Subsequently, the obtained compound was reacted with dilithiated benzene at 25 °C to form a U‐shaped precursor for CPP in a separate microreactor, which was finally dimerized and aromatized to obtain [10]CPP by a two‐step in‐flask reaction. Precise control of time and flow facilitated by the flow‐assisted system enabled the development of an efficient synthetic route for [10]CPP. 相似文献
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Dr. Nithin Suryadevara Ansgar Pausch Dr. Eufemio Moreno-Pineda Dr. Asato Mizuno Dr. Jochen Bürck Dr. Ananya Baksi Tim Hochdörffer Dr. Ivan Šalitroš Prof. Dr. Anne S. Ulrich Prof. Dr. Manfred M. Kappes Prof. Dr. Volker Schünemann Prof. Dr. Wim Klopper Prof. Dr. Mario Ruben 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(61):15172-15180
Chiral magnetic materials are proposed for applications in second-order non-linear optics, magneto-chiral dichroism, among others. Recently, we have reported a set of tetra-nuclear Fe(II) grid complex conformers with general formula C/S-[Fe4L4]8+ (L: 2,6-bis(6-(pyrazol-1-yl)pyridin-2-yl)-1,5-dihydrobenzo[1,2-d : 4,5-d′]diimidazole). In the grid complexes, isomerism emerges from tautomerism and conformational isomerism of the ligand L, and the S-type grid complex is chiral, which originates from different non-centrosymmetric spatial organization of the trans type ligand around the Fe(II) center. However, the selective preparation of an enantiomerically pure grid complex in a controlled manner is difficult due to spontaneous self-assembly. To achieve the pre-synthesis programmable resolution of Fe(II) grid complexes, we designed and synthesized two novel intrinsically chiral ligands by appending chiral moieties to the parent ligand. The complexation of these chiral ligands with Fe(II) salt resulted in the formation of enantiomerically pure Fe(II) grid complexes, as unambiguously elucidated by CD and XRD studies. The enantiomeric complexes exhibited similar gradual and half-complete thermal and photo-induced SCO characteristics. The good agreement between the experimentally obtained and calculated CD spectra further supports the enantiomeric purity of the complexes and even the magnetic studies. The chiral resolution of Fe(II)- [2×2] grid complexes reported in this study, for the first time, might enable the fabrication of magneto-chiral molecular devices. 相似文献
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Novel [2n]thiacalixarenepyrazine and [2n]thiacalixarenetriazine systems were synthesised by one-pot SNAr reactions. A screening of the metal-complexing ability of [26]hexathiacalix[3]arene[3]pyrazine revealed its affinity for CuI, CuII and AgI metal salts. 相似文献
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Dr. Dongshun Ni Sai Hu Xiangyu Tan Dr. Yang Yu Dr. Zhenghua Li Prof. Li Deng 《Angewandte Chemie (International ed. in English)》2023,62(48):e202308606
Herein, we develop a new approach to directly access architecturally complex polycyclic indolines from readily available indoles and bicyclo[1.1.0]butanes (BCBs) through formal cycloaddition promoted by commercially available Lewis acids. The reaction proceeded through a stepwise pathway involving a nucleophilic addition of indoles to BCBs followed by an intramolecular Mannich reaction to form rigid indoline-fused polycyclic structures, which resemble polycyclic indole alkaloids. This new reaction tolerated a wide range of indoles and BCBs, thereby allowing the one-step construction of various rigid indoline polycycles containing up to four contiguous quaternary carbon centers. 相似文献
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Terri C. Lovell Zachary R. Garrison Ramesh Jasti 《Angewandte Chemie (International ed. in English)》2020,59(34):14363-14367
Conjugated aromatic macrocycles are attractive due to their unique photophysical and optoelectronic properties. In particular, the cyclic radially oriented π‐system of cycloparaphenylenes (CPPs) gives rise to photophysical properties unlike any other small molecule or carbon nanomaterial. CPPs have tunable emission, possess large extinction coefficients, wide effective Stokes shifts, and high quantum yields. However, accessing bright CPPs with emissions beyond 500 nm remains difficult. Herein, we present a novel and bright orange‐emitting CPP‐based fluorophore showing a dramatic 105 nm red‐shift in emission and striking 237 nm effective Stokes shift while retaining a large quantum yield of 0.59. We postulate, and experimentally and theoretically support, that the quantum yield remains large due to the lack of intramolecular charge transfer. 相似文献
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Jing Zhang Yun‐Yun Xi Qing Li Qing Tang Ruibing Wang Ying Huang Zhu Tao Sai‐Feng Xue Leonard F. Lindoy Gang Wei 《化学:亚洲杂志》2016,11(16):2250-2254
Binding interactions between twisted cucurbit[14]uril (tQ[14]) and twenty standard amino acids (AAs) have been investigated by NMR spectroscopy and isothermal titration calorimetry (ITC) in aqueous HCl solutions and in DMSO. The results showed that tQ[14] displays clear binding affinity for AAs with a positively charged side chain or containing an aromatic ring, but weaker binding affinity for AAs with hydrophobic or polar side chains, with the binding mode depending on the type of side chain present in the AAs. 相似文献
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Eiichi Kayahara Masaya Nakano Liansheng Sun Kosuke Ishida Shigeru Yamago 《化学:亚洲杂志》2020,15(16):2451-2455
A small library of tetrasubstituted [10]cycloparaphenylene ([10]CPP) derivatives bearing alkyl, alkenyl, alkynyl and aryl substituents was constructed by a Pd‐catalyzed cross‐coupling reaction starting from tetratriflate [10]CPP 5 e , which was readily available in high yields on a >2 g scale. The CPP skeleton increases the reactivity of aryl triflate for oxidative addition to the Pd species, and 5 e is 10 times more reactive than its linear paraphenylene analogue, as determined by competition experiments. Theoretical calculations suggest that the accumulation of the small strain relief from each paraphenylene unit not involved in the reaction is responsible for the observed enhanced reactivity. 相似文献