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Large Azobenzene Macrocycles: Formation and Detection by NMR and MS Methods 大偶氮苯大环:核磁共振和质谱方法的形成和检测
IF 3.3 4区 化学 Q2 Chemistry Pub Date : 2022-02-01 DOI: 10.1080/10610278.2023.2230334
H. Roithmeyer, Merle Uudsemaa, A. Trummal, Mari-Liis Brük, Sebastian Krämer, I. Reile, Vitālijs Rjabovs, Kirsti Palmi, M. Rammo, R. Aav, Elina Kalenius, J. Adamson
ABSTRACT Azobenzene macrocycles are widely investigated as potential drug delivery systems and as part of molecular machines due to their photo-responsive properties. Herein, we detect the formation of a series of new azobenzene macrocycles that feature up to eight switchable repeating units. High-resolution mass spectrometry and ion mobility (IM) mass spectrometry experiments and 1H and diffusion-ordered spectroscopy (DOSY) NMR are used to detect the presence of the macrocycles that contain 10 to 40 aromatic rings in the gas phase and solution, respectively. The responsiveness of the Z-to-E photo-switching of the smallest of the macrocycles, exhibiting two azobenzene units and in total 10 aromatic rings, separated with column chromatography, is studied with irradiation experiments, using both UV-Vis light and thermal excitation and relaxation, and monitoring the sample with UV-Vis absorption and 1H NMR spectroscopy. DFT calculations are used to understand the conformation of this isolated species in solution.
偶氮苯大环由于其光响应特性,作为潜在的药物传递系统和分子机器的一部分被广泛研究。在这里,我们检测到一系列新的偶氮苯大环的形成,这些大环具有多达8个可切换的重复单元。采用高分辨率质谱和离子迁移率(IM)质谱实验以及1H和扩散有序谱(DOSY) NMR分别检测气相和溶液中含有10 ~ 40个芳环的大环的存在。采用紫外-可见光、热激发和弛豫的辐照实验,利用紫外-可见吸收和1H NMR光谱监测样品,研究了最小的大环(含2个偶氮苯单元和共10个芳环)的z - e光开关的响应性。DFT计算被用来理解这个孤立的物种在溶液中的构象。
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引用次数: 0
Model binding experiments with cucurbit[7]uril and p-sulfonatocalix[4]arene support use of explicit solvation term in governing equation for binding equilibria 葫芦丝[7]脲和对磺酰基[4]芳烃的模型结合实验支持在结合平衡控制方程中使用显式溶剂化项
IF 3.3 4区 化学 Q2 Chemistry Pub Date : 2022-02-01 DOI: 10.1080/10610278.2023.2254442
D. Eggers, Adam Brewer, Kimberly J. Cacatian, L. A. Camat, Dominic Castagnoli, Nina Chuang, Lillian N. Chung, Thanh Do, Emily Huynh, Thanayuth Jenpichitkulchai, Anoop Kaur, Frank Le, Roy Ong, Duc Pham, Kevin Shao
ABSTRACT The thermodynamics of model host–guest-binding reactions is examined in depth using isothermal titration calorimetry. In conflict with classical thermodynamics, the results indicate that the equilibrium-binding quotient, K, is not a constant for all pairings. This outcome is predicted by an equation for binding equilibria that includes an explicit term for the change in solvation free energy that accompanies the formation of a binary complex. Application of this framework to the experimentally observed concentration dependence of K allows one to obtain the energetic contribution of the solvent, a linked equilibrium denoted here as ΔG H2O. The estimated values of ΔG H2O are large and unfavourable for the binding of selected guest molecules to two hosts, cucurbit[7]uril and p-sulfonatocalix[4]arene. Intriguingly, the estimated values of ΔG H2O are near zero for the binding of two hydrophobic guest molecules to β-cyclodextrin, leading to a thought-provoking discussion on the driving force behind the hydrophobic effect. Graphical abstract
采用等温滴定量热法对模型主-客体结合反应的热力学进行了深入研究。与经典热力学相矛盾的是,结果表明平衡结合商K不是所有配对的常数。这一结果是由一个结合平衡方程预测的,其中包括伴随二元配合物形成的溶剂化自由能变化的显式项。将这一框架应用于实验观察到的K的浓度依赖性,可以得到溶剂的能量贡献,这里表示为ΔG H2O的链接平衡。ΔG H2O的估定值较大,不利于选定的客体分子与两种寄主(葫芦[7]脲和对磺酰基[4]芳烃)结合。有趣的是,对于两个疏水来宾分子与β-环糊精的结合,ΔG H2O的估价值接近于零,这引发了关于疏水效应背后驱动力的发人深省的讨论。图形抽象
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引用次数: 1
Controlling selective formation of [2]- and [3]-pseudorotaxanes by tuning spacer length of guests 通过调节客体的间隔长度来控制[2]-和[3]-伪环紫杉烷的选择性形成
IF 3.3 4区 化学 Q2 Chemistry Pub Date : 2022-02-01 DOI: 10.1080/10610278.2023.2223333
Jinyang Wu, Long Chen, Xuan Sun, Song Huang, Xiaowei Li, Wen Feng, Li-hua Yuan
ABSTRACT Exploration of host–guest complexation between a shape-persistent H-bonded macrocycle and flexible guests may enable construction of new pseudorotaxanes systems. Here, we present the impact of varying the spacer length of four bis(4-phenylpyridinium) guests G1-G4 on production of pseudorotaxanes with a 2D H-bonded macrocycle 1a. The host–guest complexes are probed by 1H NMR, 2D NOESY and UV–vis spectroscopic techniques. [2]- and [3]- pseudorotaxane assemblies are formed specifically using these guests, demonstrating the dependency of accessing [2]- and [3]- pseudorotaxane on the spacer length of these dications. Theoretical calculations reveal the difference in the conformation of the guests between these two binding modes: the one with a 1:1 stoichiometry (spacer length: C4 and C6) show Z-shaped conformation and the other with a 2:1 stoichiometry (spacer length: C8 and C10) take a linear conformation. The findings of the threading modes may help develop new H-bonded macrocycle-based rotaxanes and other related mechanically interlocked molecules. GRAPHICAL ABSTRACT
探索形状持久的h键大环与柔性客体之间的主客体络合作用,可能有助于构建新的假环紫杉烷体系。在这里,我们研究了改变四个双(4-苯基吡啶)客体G1-G4的间隔长度对用2D氢键大环1a生产假环紫杉烷的影响。采用1H NMR, 2D NOESY和UV-vis光谱技术对主客体配合物进行了探测。[2]-和[3]- pseudorotaxane组件是专门使用这些来宾形成的,这表明访问[2]-和[3]- pseudorotaxane依赖于这些指示的间隔长度。理论计算揭示了这两种结合模式之间的宾客构象差异:化学计量比为1:1(间隔长度:C4和C6)的宾客构象为z形,化学计量比为2:1(间隔长度:C8和C10)的宾客构象为线性。研究结果可能有助于开发新的基于h键大环的轮烷和其他相关的机械互锁分子。图形抽象
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引用次数: 0
NASC: bringing together supramolecular chemists from across North America NASC:汇集了来自北美各地的超分子化学家
IF 3.3 4区 化学 Q2 Chemistry Pub Date : 2022-01-02 DOI: 10.1080/10610278.2023.2178724
Nathalie Busschaert, Víctor García‐López, Chenfeng Ke, C. McGuirk, L. S. Shimizu, Margaret C. Gerthoffer, Nabarupa Bhattacharjee
ABSTRACT Early-career scientists need opportunities to present their research and to network. Although within the supramolecular chemistry community, local conferences that provide such opportunities have arisen over the last few decades, a suitable conference in North America had not been organised. To counter this situation, in 2022, we (Nathalie Busschaert (Tulane) and Clifton J Stephenson (Loyola University of New Orleans)) organised the first North American Supramolecular Chemistry (NASC) meeting to bring together supramolecular chemists from across the continent and to provide career-building opportunities for PhD students and postdocs. For this Conference Proceeding, we asked some of the invited speakers, as well as the winners of the best talk prizes, to provide their opinion of the meeting and their vision on the future of supramolecular chemistry in North America. Graphical abstract
职业生涯早期的科学家需要机会来展示他们的研究成果并建立人际关系。虽然在过去的几十年里,在超分子化学领域出现了提供这种机会的地方会议,但是在北美还没有组织一个合适的会议。为了应对这种情况,在2022年,我们(Nathalie Busschaert(杜兰大学)和Clifton J Stephenson(新奥尔良洛约拉大学))组织了第一次北美超分子化学(NASC)会议,汇集了来自整个大陆的超分子化学家,并为博士生和博士后提供了职业发展机会。在本次会议记录中,我们邀请了一些受邀的演讲者,以及最佳演讲奖的获奖者,提供他们对这次会议的看法以及他们对北美超分子化学未来的看法。图形抽象
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引用次数: 0
Global analysis for pD-variation NMR titration of organic electrolyte complexes 有机电解质配合物pd变化核磁共振滴定的全局分析
IF 3.3 4区 化学 Q2 Chemistry Pub Date : 2022-01-02 DOI: 10.1080/10610278.2023.2174025
R. Navarro, Yedith Soberanes, M. Inoue
ABSTRACT This is an addendum to our preceding article, ‘NMR pD-variation method to determine the proper stabilities of organic electrolyte complexes: case of histidine complexes with a cyclophane acid’ Supramolecular Chemistry https://doi.org/10.1080/10610278.2022.2134017, which proposes that the species distribution of complexes between organic electrolytes is determined by observing the pD dependence of NMR signals for a mixture of the reactants; the species distribution can be replotted in a pH scale. This addendum demonstrates that the process of data analysis is simplified even more reliably by employing a global fitting method in place of a local, successive method used previously; comparative evaluation was made using Excel® spreadsheets appended. The straightforward global analysis will facilitate the practice of pD-variation NMR titration. The application range is potentially extendable by the use of 13C NMR, which overcomes some weak points of the 1H NMR method. Grapical abstract
这是我们上一篇文章《确定有机电解质配合物适当稳定性的核磁共振pD-变化方法:组氨酸与环烷酸配合物的案例》(supermolecular Chemistry https://doi.org/10.1080/10610278.2022.2134017)的补充,该文章提出,有机电解质之间配合物的种类分布是通过观察混合物的核磁共振信号的pD依赖性来确定的;物种分布可以在pH值范围内重新绘制。本附录表明,采用全局拟合方法代替以前使用的局部连续方法,可以更可靠地简化数据分析过程;采用所附Excel®电子表格进行对比评价。直接的全局分析将促进pd变化核磁共振滴定的实践。13C核磁共振的应用范围有可能扩大,克服了1H核磁共振方法的一些弱点。Grapical文摘
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引用次数: 0
Statement of Retraction 撤回声明
IF 3.3 4区 化学 Q2 Chemistry Pub Date : 2022-01-02 DOI: 10.1080/10610278.2023.2176013
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引用次数: 0
Tripodal 1,3,5-benzenetricarboxamide ligand with dipicolinic acid units and its binding with Eu(III) ions 具有二吡啶酸单位的三足1,3,5-苯三羧基酰胺配体及其与Eu(III)离子的结合
IF 3.3 4区 化学 Q2 Chemistry Pub Date : 2022-01-02 DOI: 10.1080/10610278.2023.2177162
Niklas Klangwart, Céline Ruijs, C. Hawes, T. Gunnlaugsson, O. Kotova
ABSTRACT The synthesis and characterisation of tripodal ligand 1 containing 1,3,5-benzenetricarboxamide core and diethyl 4-(phenylethynyl)pyridine-2,6-dicarboxylate is described. The crystal structure of the intermediate tripodal molecule 7 exhibits an unusual staggered hydrogen-bonded chain motif instead of the anticipated helical assembly. We studied the basic photophysical properties of 1 in solvents of various polarity including CH3OH, CH3CN, DMSO, and CHCl3. The self-assembly experiments between 1 and Eu(CF3SO3)3⋅6H2O confirmed the formation of metal-ligand self-assembly species in the solution of CH3CN. It was also shown that the excitation of the Eu(III)-centred emission in such species occurred through the energy transfer from the ligand acting as an antenna to the metal centre. The binding constant values were evaluated using the nonlinear regression analysis software SPECFIT®, and their values correspond to those previously observed for the assemblies between 2,6-dipicolinic acid derivatives and lanthanide ions. This work describes the synthesis of tripodal 1,3,5-benzenetricarboxamide ligand with dipicolinic acid units and its binding with Eu(III) ions in solution. The photophysical properties of the target tripodal ligand were studied in solvents of various polarity. The self-assembly experiments between the ligand and Eu(III) ions in solution confirmed the formation of luminescent metal-ligand self-assembly species. Graphical abstract
摘要:本文报道了含有1,3,5-苯三羧基酰胺核和4-(苯乙基)吡啶-2,6-二羧酸二乙酯的三足配体1的合成和表征。中间三足分子7的晶体结构表现出不寻常的交错氢键链基序,而不是预期的螺旋组装。我们研究了1在不同极性溶剂中的基本光物理性质,包括CH3OH, CH3CN, DMSO和CHCl3。1与Eu(CF3SO3)3⋅6H2O之间的自组装实验证实了在CH3CN溶液中金属配体自组装物质的形成。研究还表明,在这些物质中,Eu(III)中心辐射的激发是通过能量从作为天线的配体转移到金属中心而发生的。使用非线性回归分析软件SPECFIT®评估结合常数值,其值与先前观察到的2,6-二吡啶酸衍生物与镧系离子之间的组装相对应。本文描述了以二吡啶酸为单位的三足1,3,5-苯三羧基酰胺配体的合成及其在溶液中与Eu(III)离子的结合。研究了目标三足配体在不同极性溶剂中的光物理性质。配体与溶液中Eu(III)离子的自组装实验证实了发光金属-配体自组装物质的形成。图形抽象
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引用次数: 0
Bacterial cytological profiling identifies transmembrane anion transport as the mechanism of action for a urea-based antibiotic 细菌细胞学分析确定跨膜阴离子运输作为尿素基抗生素的作用机制
IF 3.3 4区 化学 Q2 Chemistry Pub Date : 2022-01-02 DOI: 10.1080/10610278.2023.2178921
Sarah R. Herschede, R. Salam, Hassan Gneid, Nathalie Busschaert
ABSTRACT There is a growing fear that bacteria are emerging that are resistant to most known antibiotics, which could lead to an increasing number of fatalities due to bacterial infections. There is therefore an urgent need for the development of novel antibacterial products, preferably with novel mode of actions for which there are no known resistance pathways. We have previously found serendipitously that a simple urea-based compound functions as a potent antibacterial agent. In this manuscript, we use bacterial cytological profiling (BCP) to determine its mechanism of action. BCP reveals that the urea is acting through a membrane-based pathway that is comparable to, but distinct from, the mechanism of cationophore calcimycin. Additional liposome-based assays suggest that the likely mechanism of action of this mono-urea is transmembrane anion transport. This finding highlights that synthetic anionophores could be used as potential antibiotics. Graphical abstract
人们越来越担心出现对大多数已知抗生素具有耐药性的细菌,这可能导致因细菌感染而死亡的人数增加。因此,迫切需要开发新的抗菌产品,最好是具有新的作用模式,没有已知的耐药途径。我们以前偶然发现了一种简单的尿素基化合物作为一种有效的抗菌剂。在这篇文章中,我们使用细菌细胞学分析(BCP)来确定其作用机制。BCP表明,尿素通过一种基于膜的途径起作用,这种途径与钙霉素的机制相似,但又不同。其他基于脂质体的分析表明,这种单尿素的作用机制可能是跨膜阴离子运输。这一发现突出表明,人工合成的阴离子载体可以用作潜在的抗生素。图形抽象
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引用次数: 2
A dual-functional chemosensor based on phenazine derivative for detecting toxic ions in water samples and cosmetic 基于非那嗪衍生物的双功能化学传感器用于水样和化妆品中有毒离子的检测
IF 3.3 4区 化学 Q2 Chemistry Pub Date : 2022-01-02 DOI: 10.1080/10610278.2023.2213795
Yuhu Che, Xiao-Ni Qi, Wen-juan Qu, Qi Lin, Hong Yao, You‐Ming Zhang, T. Wei
ABSTRACT Selective monitoring and targeted identification of various noxious ions have received significant attention in biology, industry and environments. Herein, we developed an easily available colorimetric and fluorescence sensor (PZ) based on phenazine derivative, successfully achieving the discriminative detection of Hg2+ and CN− ions. Compared with other interfering ions, PZ had high sensitivity and specificity towards Hg2+ and CN−. The lowest limits of Hg2+ and CN- by PZ were 1.52 × 10−8 M and 7.05 × 10−7 M, respectively. Significantly, this chemosensor PZ allowed visual monitoring of toxic Hg2+ and CN− ions in a few seconds, presenting a great potential in the practical application (skin-whitening cosmetic, water samples, and nutlet). Such an effective strategy is expected to offer some guidance for distinguishing the identification of toxic ions in optical sensing. Graphical abstract
各种有害离子的选择性监测和靶向鉴定在生物学、工业和环境领域受到广泛关注。在此,我们开发了一种易于获得的基于非那嗪衍生物的比色和荧光传感器(PZ),成功地实现了Hg2+和CN−离子的鉴别检测。与其他干扰离子相比,PZ对Hg2+和CN−具有较高的敏感性和特异性。PZ对Hg2+和CN-的下限分别为1.52 × 10−8 M和7.05 × 10−7 M。值得注意的是,这种化学传感器PZ可以在几秒钟内对有毒的Hg2+和CN -离子进行视觉监测,在实际应用(皮肤美白化妆品,水样和坚果)中具有很大的潜力。这种有效的策略有望为光学传感中有毒离子的鉴别提供一定的指导。图形抽象
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引用次数: 0
(Self) assembled news: recent highlights from the supramolecular chemistry literature (Quarter 1, 2023) (自我)汇编新闻:超分子化学文献的最新亮点(2023年第1季度)
IF 3.3 4区 化学 Q2 Chemistry Pub Date : 2022-01-02 DOI: 10.1080/10610278.2023.2189346
Cally J. E. Haynes, Nicholas G. White
The synthesis of pillar[n]arene macrocycles has been one of the most influential developments in the recent history of supramolecular chemistry. These macrocycles have a rich host – guest chemistry and can often be prepared in a single step. Writing in Nature Synthesis, a team led by Andrew Sue (winner of the 2021 Sessler Early Career Research Prize) have shown that pillar[5] arene derivatives can be used to form well-defined chiral nanotubes [1]. The nanotubes are formed in a singlestep condensation reaction of a penta-formyl macrocycle and phenylenediamine in quantitative yield (Figure 1). The penta-formyl compound was previously reported by the same group and was synthesised from tiara[5]arene, which was itself prepared from a rimdifferentiated pillar[5]arene [2]. Pillar[5]arenes are chiral but racemise rapidly in solution through rotation of the rings; however, in the nanotubes this rotation is locked and a pair of enantiomeric tubes were formed that could be separated using chiral HPLC. While the binding of chiral guests was not investigated, the nanotubes show strong binding of dihydroxyalkanes and dibromoalkanes with selectivity based on guest size.
柱[n]芳烃大环的合成是近年来超分子化学史上最具影响力的发展之一。这些大环具有丰富的主客体化学性质,通常可以在一个步骤中制备。由Andrew Sue(2021年Sessler早期职业研究奖得主)领导的团队在Nature Synthesis上发表的文章表明,柱[5]芳烃衍生物可用于形成定义良好的手性纳米管[1]。纳米管是由五甲酰基大环和苯二胺的单步缩合反应形成的(图1)。该五甲酰基化合物先前由同一小组报道,由冠状[5]芳烃合成,冠状[5]芳烃本身是由未分化柱状[5]芳烃[2]制备的。柱[5]芳烃是手性的,但通过环的旋转在溶液中迅速外消旋;然而,在纳米管中,这种旋转是锁定的,形成了一对可以用手性高效液相色谱分离的对映体管。虽然没有研究手性客体的结合,但纳米管对二羟基烷烃和二溴烷烃的结合表现出很强的选择性,并基于客体的大小。
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引用次数: 0
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Supramolecular Chemistry
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