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Journal articles on the topic 'Mechanically interlocked molecules (MIMs)'

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Published: 7 July 2024

Last updated: 7 July 2024

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1

van Maarseveen, Jan H., Milo D. Cornelissen, and Simone Pilon. "Covalently Templated Syntheses of Mechanically Interlocked Molecules." Synthesis 53, no. 24 (October 8, 2021): 4527–48. http://dx.doi.org/10.1055/a-1665-4650.

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AbstractMechanically interlocked molecules (MiMs), such as catenanes and rotaxanes, exhibit unique properties due to the mechanical bond which unites their components. The translational and rotational freedom present in these compounds may be harnessed to create stimuli-responsive MiMs, which find potential application as artificial molecular machines. Mechanically interlocked structures such as lasso peptides have also been found in nature, making MiMs promising albeit elusive targets for drug discovery. Although the first syntheses of MiMs were based on covalent strategies, approaches based on non-covalent interactions rose to prominence thereafter and have remained dominant. Non-covalent strategies are generally short and efficient, but do require particular structural motifs which are difficult to alter. In a covalent approach, MiMs can be more easily modified while the components may have increased rotational and translational freedom. Both approaches have complementary merits and combining the unmatched efficiency of non-covalent approaches with the scope of covalent syntheses may open up vast opportunities. In this review, recent covalently templated syntheses of MiMs are discussed to show their complementarity and anticipate future developments in this field.1 Introduction2 Tetrahedral Templates2.1 A Carbonate Template for Non-Rusty Catenanes2.2 All-Benzene Catenanes on a Silicon Template2.3 Backfolding from Quaternary Carbon3 Planar Templates3.1 Rotaxanes Constructed in a Ring3.2 Hydrindacene as a Dynamic Covalent Template3.3 Templating on Tri- and Tetrasubstituted Benzenes4 Conclusion

2

Krajnc, Matthias, and Jochen Niemeyer. "BINOL as a chiral element in mechanically interlocked molecules." Beilstein Journal of Organic Chemistry 18 (May 6, 2022): 508–23. http://dx.doi.org/10.3762/bjoc.18.53.

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In this minireview we present the use of the axially chiral 1,1'-binaphthyl-2,2'-diol (BINOL) unit as a stereogenic element in mechanically interlocked molecules (MIMs). We describe the synthesis and properties of such BINOL-based chiral MIMs, together with their use in further diastereoselective modifications, their application in asymmetric catalysis, and their use in stereoselective chemosensing. Given the growing importance of mechanically interlocked molecules and the key advantages of the privileged chiral BINOL backbone, we believe that this research area will continue to grow and deliver many useful applications in the future.

3

Kwan, Chak-Shing, and Ken Cham-Fai Leung. "Development and advancement of rotaxane dendrimers as switchable macromolecular machines." Materials Chemistry Frontiers 4, no. 10 (2020): 2825–44. http://dx.doi.org/10.1039/d0qm00368a.

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Rotaxane dendrimers are a newly emerging large family of mechanically interlocked molecules (MIMs), which combine the concept of molecular switching properties into hyperbranched dendrimers to render new macromolecular machines.

4

Stasyuk, Anton, Olga Stasyuk, Miquel Solà, and Alexander A. Voityuk. "(Invited) Photoinduced Electron Transfer in Mechanically Interlocked Suit[3]Ane Systems." ECS Meeting Abstracts MA2022-02, no. 57 (October 9, 2022): 2183. http://dx.doi.org/10.1149/ma2022-02572183mtgabs.

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Mechanically interlocked molecules (MIMs) attract significant attention of scientists over the past few decades due to their unusual architecture. For a long time, architectures of MIMs were represented by catenanes, rotaxanes, molecular knots, and their derivatives. Only several years ago, a new type of MIMs that do not possess interlocked rings or dumbbell shaped molecule threaded through a macroring was introduced. Suitanes – a class of MIMs, which consist of two separate components - contains a body with two or more rigid limbs protruding outwards and a close-fitting, all-in-one suit. We present the results of computational modelling of the photoinduced processes in the recently reported by F. Stoddart two-component MIM - suit[3]ane, and similar systems with aromatic 3-fold symmetric bodies.[1] The reported suit[3]ane contains a benzotrithiophene (BTT) derivative with three n-hexyl substituents (BTT-3C6 ) as a body and 3-fold symmetric pyridinium-based cage, namely HexaCage6+ (HC6+∙6PF6 - ), as a suit. Analysis of the ground state properties of the suit[3]anes show that low LUMO of HC6+∙6PF6 - and its ability to delocalize charge make this cage an efficient electron acceptor. The TDDFT calculations for a series of inclusion complexes (HC6+∙6PF6 - ⊃ XXX, where XXX are aromatic 3-fold symmetric bodies) revealed that the photoinduced electron transfer process is favorable not only for the complexes with strong donors, such as thiatruxene or benzotrithiophenes, but also for poor donors, such as benzotrifuran. The photoinduced charge separation in the studied complexes occurs on a picosecond time scale. The computations predicts very similar electronic properties not only for single unit of suit[3]ane but also for its aggregates. The high stability of suit[3]anes in combination with their photoinduced electron transfer properties makes this new class of interlocked molecules promising materials for photovoltaic applications.[2] References: [1] J. F. Stoddart et al., J. Am. Chem. Soc. 2020, 142, 20152. [2] A.J. Stasyuk et al., J. Mater. Chem. C, 2021, 9, 9436. Figure 1

5

Stoddart, J. Fraser. "Mechanically Interlocked Molecules (MIMs)-Molecular Shuttles, Switches, and Machines (Nobel Lecture)." Angewandte Chemie International Edition 56, no. 37 (August 16, 2017): 11094–125. http://dx.doi.org/10.1002/anie.201703216.

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6

Schröder, Hendrik V., and Christoph A. Schalley. "Tetrathiafulvalene – a redox-switchable building block to control motion in mechanically interlocked molecules." Beilstein Journal of Organic Chemistry 14 (August 20, 2018): 2163–85. http://dx.doi.org/10.3762/bjoc.14.190.

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With the rise of artificial molecular machines, control of motion on the nanoscale has become a major contemporary research challenge. Tetrathiafulvalenes (TTFs) are one of the most versatile and widely used molecular redox switches to generate and control molecular motion. TTF can easily be implemented as functional unit into molecular and supramolecular structures and can be reversibly oxidized to a stable radical cation or dication. For over 20 years, TTFs have been key building blocks for the construction of redox-switchable mechanically interlocked molecules (MIMs) and their electrochemical operation has been thoroughly investigated. In this review, we provide an introduction into the field of TTF-based MIMs and their applications. A brief historical overview and a selection of important examples from the past until now are given. Furthermore, we will highlight our latest research on TTF-based rotaxanes.

7

Stoddart, J. Fraser. "Putting Mechanically Interlocked Molecules (MIMs) to Work in Tomorrow’s World." Angewandte Chemie International Edition 53, no. 42 (September 24, 2014): 11102–4. http://dx.doi.org/10.1002/anie.201408043.

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8

Anghel, Cătălin C., Teodor A. Cucuiet, Niculina D. Hădade, and Ion Grosu. "Active-metal template clipping synthesis of novel [2]rotaxanes." Beilstein Journal of Organic Chemistry 19 (November 20, 2023): 1776–84. http://dx.doi.org/10.3762/bjoc.19.130.

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Mechanically interlocked molecules (MIMs) have been important synthetic targets in supramolecular chemistry due to their beautiful structures and intriguing properties. We present herein a new synthetic strategy to access [2]rotaxanes, namely active-metal template clipping. We discuss the design of the target [2]rotaxanes, synthesis and characterization of the axle, macrocycle precursors and macrocycles as well as preparation of the final [2]rotaxanes by active template copper(I)-catalyzed alkyne–azide cycloaddition (CuAAC) as key step of the synthesis. HRMS and NMR experiments have been performed to confirm the formation of the interlocked structures.

9

Rashid, Showkat, Yusuke Yoshigoe, and Shinichi Saito. "Phenanthroline based rotaxanes: recent developments in syntheses and applications." RSC Advances 12, no. 18 (2022): 11318–44. http://dx.doi.org/10.1039/d2ra01318e.

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The advancements in the field of mechanically interlocked molecular systems (MIMs) has concurrently restructured the material chemistry frontiers and provided ample scope to explore new dimensions for applications and diversity creation.

10

Barin, Gokhan, Ross S. Forgan, and J. Fraser Stoddart. "Mechanostereochemistry and the mechanical bond." Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences 468, no. 2146 (May 9, 2012): 2849–80. http://dx.doi.org/10.1098/rspa.2012.0117.

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The chemistry of mechanically interlocked molecules (MIMs), in which two or more covalently linked components are held together by mechanical bonds , has led to the coining of the term mechanostereochemistry to describe a new field of chemistry that embraces many aspects of MIMs, including their syntheses, properties, topologies where relevant and functions where operative. During the rapid development and emergence of the field, the synthesis of MIMs has witnessed the forsaking of the early and grossly inefficient statistical approaches for template-directed protocols, aided and abetted by molecular recognition processes and the tenets of self-assembly. The resounding success of these synthetic protocols, based on templation, has facilitated the design and construction of artificial molecular switches and machines, resulting more and more in the creation of integrated functional systems. This review highlights (i) the range of template-directed synthetic methods being used currently in the preparation of MIMs; (ii) the syntheses of topologically complex knots and links in the form of stable molecular compounds; and (iii) the incorporation of bistable MIMs into many different device settings associated with surfaces, nanoparticles and solid-state materials in response to the needs of particular applications that are perceived to be fair game for mechanostereochemistry.

11

Mat Yassin, Ubaidullah Hj, Malai Haniti Sheikh Abdul Hamid, Zainab Ngaini, and Ai Ling Tan. "Different synthetic approaches, design and applications of metal–organic frameworks with selected organic ligands." Scientia Bruneiana 18, no. 2 (June 23, 2020): 40–68. http://dx.doi.org/10.46537/scibru.v18i2.107.

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Metal-organic frameworks (MOFs) bearing a number of organic ligands of various functional groups and substituents give rise to MOFs of unique crystal structures and topologies. A number of potential applications have been considered for these materials in a wide array of scientific fields, such as in the adsorption of industrially-relevant gases, as heterogeneous catalysts for various organic reactions, as photoluminescent materials, and as antibacterial agents. This review highlights the utility of select groups of organic ligands in the assembly of main group metals, transition metals, as well as lanthanides and actinides, to generate MOFs of diverse structures in the solid state, with special attention paid on ligands bearing the carboxylate-, pyridyl-, ether-, imine (Schiff base) moieties, as well as mechanically interlocked molecules (MIMs).

12

Wang, Wei, Wei Wu, and Peifeng Su. "Radical Pairing Interactions and Donor–Acceptor Interactions in Cyclobis(Paraquat-P-Phenylene) Inclusion Complexes." Molecules 28, no. 5 (February 22, 2023): 2057. http://dx.doi.org/10.3390/molecules28052057.

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Understanding molecular interactions in mechanically interlocked molecules (MIMs) is challenging because they can be either donor–acceptor interactions or radical pairing interactions, depending on the charge states and multiplicities in the different components of the MIMs. In this work, for the first time, the interactions between cyclobis(paraquat-p-phenylene) (abbreviated as CBPQTn+ (n = 0–4)) and a series of recognition units (RUs) were investigated using the energy decomposition analysis approach (EDA). These RUs include bipyridinium radical cation (BIPY•+), naphthalene-1,8:4,5-bis(dicarboximide) radical anion (NDI•−), their oxidized states (BIPY2+ and NDI), neutral electron-rich tetrathiafulvalene (TTF) and neutral bis-dithiazolyl radical (BTA•). The results of generalized Kohn–Sham energy decomposition analysis (GKS-EDA) reveal that for the CBPQTn+···RU interactions, correlation/dispersion terms always have large contributions, while electrostatic and desolvation terms are sensitive to the variation in charge states in CBPQTn+ and RU. For all the CBPQTn+···RU interactions, desolvation terms always tend to overcome the repulsive electrostatic interactions between the CBPQT cation and RU cation. Electrostatic interaction is important when RU has the negative charge. Moreover, the different physical origins of donor–acceptor interactions and radical pairing interactions are compared and discussed. Compared to donor–acceptor interactions, in radical pairing interactions, the polarization term is always small, while the correlation/dispersion term is important. With regard to donor–acceptor interactions, in some cases, polarization terms could be quite large due to the electron transfer between the CBPQT ring and RU, which responds to the large geometrical relaxation of the whole systems.

13

Hu, Fang, Ziyong Li, Xing Li, Jun Yin, and Sheng Liu. "Photochromism in Mechanically Interlocked Molecules." Current Organic Chemistry 21, no. 5 (January 10, 2017): 450–62. http://dx.doi.org/10.2174/1385272820666160919105428.

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14

Pearce, Nicholas, Marysia Tarnowska, Nathan J. Andersen, Alexander Wahrhaftig-Lewis, Ben S. Pilgrim, and Neil R. Champness. "Mechanically interlocked molecular handcuffs." Chemical Science 13, no. 14 (2022): 3915–41. http://dx.doi.org/10.1039/d2sc00568a.

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Mechanically interlocked molecules that employ a handcuff component provide a pathway to highly unusual structures, a new nomenclature is proposed which helps to identify opportunities for employing this structural unit for new architectures.

15

Ikeda, Taichi, and James Fraser Stoddart. "Electrochromic materials using mechanically interlocked molecules." Science and Technology of Advanced Materials 9, no. 1 (January 2008): 014104. http://dx.doi.org/10.1088/1468-6996/9/1/014104.

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16

Davis, Jason J., Grzegorz A. Orlowski, Habibur Rahman, and Paul D. Beer. "Mechanically interlocked and switchable molecules at surfaces." Chem. Commun. 46, no. 1 (2010): 54–63. http://dx.doi.org/10.1039/b915122b.

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17

Zhou, He-Ye, Ying Han, and Chuan-Feng Chen. "pH-Controlled motions in mechanically interlocked molecules." Materials Chemistry Frontiers 4, no. 1 (2020): 12–28. http://dx.doi.org/10.1039/c9qm00546c.

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18

Niemeyer, Jochen, and Noel Pairault. "Chiral Mechanically Interlocked Molecules – Applications of Rotaxanes, Catenanes and Molecular Knots in Stereoselective Chemosensing and Catalysis." Synlett 29, no. 06 (February 26, 2018): 689–98. http://dx.doi.org/10.1055/s-0036-1591934.

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Interlocked molecules, such as rotaxanes, catenanes, and molecular knots, offer conceptually new possibilities for the generation of chiral chemosensors and catalysts. Due to the presence of the mechanical or topological bond, interlocked molecules can be used to design functional systems with unprecedented features, such as switchability and deep binding cavities. In addition, classical elements of chirality can be supplemented with mechanical or topological chirality, which have so far only scarcely been employed as sources of chirality for stereoselective applications. This minireview discusses recent examples in this emerging area, showing that the application of chiral interlocked molecules in sensing and catalysis offers many fascinating opportunities for future research.1 Introduction2 Interlocked Molecules with Chiral Subcomponents2.1 Point Chirality2.2 Axial Chirality3 Mechanically Chiral Interlocked Molecules4 Topologically Chiral Interlocked Molecules5 Outlook

19

Nisanci, Bilal, Sinem Sahinoglu, Esra Tuner, Mustafa Arik, İbrahim Kani, Arif Dastan, and Özgür Altan Bozdemir. "Synthesis of an F-BODIPY [2]catenane using the chemistry of bis(dipyrrinato)metal complexes." Chemical Communications 53, no. 92 (2017): 12418–21. http://dx.doi.org/10.1039/c7cc07021g.

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20

Sluysmans, Damien, and J. Fraser Stoddart. "The Burgeoning of Mechanically Interlocked Molecules in Chemistry." Trends in Chemistry 1, no. 2 (May 2019): 185–97. http://dx.doi.org/10.1016/j.trechm.2019.02.013.

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21

Barin, Gokhan, Ali Coskun, Moustafa M. G. Fouda, and J. Fraser Stoddart. "Mechanically Interlocked Molecules Assembled by π-π Recognition." ChemPlusChem 77, no. 3 (February 28, 2012): 159–85. http://dx.doi.org/10.1002/cplu.201100075.

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22

Lewis, James E. M., Paul D. Beer, Stephen J. Loeb, and Stephen M. Goldup. "Metal ions in the synthesis of interlocked molecules and materials." Chemical Society Reviews 46, no. 9 (2017): 2577–91. http://dx.doi.org/10.1039/c7cs00199a.

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23

Lewis, James E. M., Marzia Galli, and Stephen M. Goldup. "Properties and emerging applications of mechanically interlocked ligands." Chemical Communications 53, no. 2 (2017): 298–312. http://dx.doi.org/10.1039/c6cc07377h.

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24

Hoyas Pérez, Nadia, and James E. M. Lewis. "Synthetic strategies towards mechanically interlocked oligomers and polymers." Organic & Biomolecular Chemistry 18, no. 35 (2020): 6757–80. http://dx.doi.org/10.1039/d0ob01583k.

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25

Nakazono, Kazuko, and Toshikazu Takata. "Mechanical Chirality of Rotaxanes: Synthesis and Function." Symmetry 12, no. 1 (January 10, 2020): 144. http://dx.doi.org/10.3390/sym12010144.

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Mechanically chiral molecules have attracted considerable attention due to their property and function based on its unique interlocked structure. This review covers the recent advances in the synthesis and function of interlocked rotaxanes with mechanical chirality along with their dynamic and complex stereochemistry. The application of mechanically chiral rotaxanes to control the polymer helical structure is also introduced, where amplification of mechanical chirality appears to cause the macroscopic polymer property change, suggesting the potential applicability of mechanical chirality in polymer systems.

26

Griffiths, Kirsten E., and J. Fraser Stoddart. "Template-directed synthesis of donor/acceptor [2]catenanes and [2]rotaxanes." Pure and Applied Chemistry 80, no. 3 (January 1, 2008): 485–506. http://dx.doi.org/10.1351/pac200880030485.

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The synthesis of mechanically interlocked molecular compounds has advanced by leaps and bounds since the early days of statistical methods and covalent-directing strategies. Template-directed synthesis has emerged as the method of choice for the construction of increasingly complex and functional [2]catenanes and [2]rotaxanes. In particular, mechanically interlocked molecules employing π-donating and π-accepting recognition units have been produced with remarkable efficiencies and show great promise in technologies as diverse as molecular electronics and drug delivery.

27

Kim, Kimoon. "Mechanically interlocked molecules incorporating cucurbituril and their supramolecular assemblies." Chemical Society Reviews 31, no. 2 (January 21, 2002): 96–107. http://dx.doi.org/10.1039/a900939f.

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28

RAYMO, F. M., and J. F. STODDART. "ChemInform Abstract: Mechanically Interlocked Molecules: Prototypes of Molecular Machinery." ChemInform 28, no. 25 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199725294.

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29

Wang, Wei, Li-Jun Chen, Xu-Qing Wang, Bin Sun, Xiaopeng Li, Yanyan Zhang, Jiameng Shi, et al. "Organometallic rotaxane dendrimers with fourth-generation mechanically interlocked branches." Proceedings of the National Academy of Sciences 112, no. 18 (April 20, 2015): 5597–601. http://dx.doi.org/10.1073/pnas.1500489112.

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Mechanically interlocked molecules, such as catenanes, rotaxanes, and knots, have applications in information storage, switching devices, and chemical catalysis. Rotaxanes are dumbbell-shaped molecules that are threaded through a large ring, and the relative motion of the two components along each other can respond to external stimuli. Multiple rotaxane units can amplify responsiveness, and repetitively branched molecules—dendrimers—can serve as vehicles for assembly of many rotaxanes on single, monodisperse compounds. Here, we report the synthesis of higher-generation rotaxane dendrimers by a divergent approach. Linkages were introduced as spacer elements to reduce crowding and to facilitate rotaxane motion, even at the congested periphery of the compounds up to the fourth generation. The structures were characterized by 1D multinuclear (1H, 13C, and 31P) and 2D NMR spectroscopy, MALDI-TOF-MS, gel permeation chromatography (GPC), and microscopy-based methods including atomic force microscopy (AFM) and transmission electron microscopy (TEM). AFM and TEM studies of rotaxane dendrimers vs. model dendrimers show that the rotaxane units enhance the rigidity and reduce the tendency of these assemblies to collapse by self-folding. Surface functionalization of the dendrimers with ferrocenes as termini produced electrochemically active assemblies. The preparation of dendrimers with a well-defined topological structure, enhanced rigidity, and diverse functional groups opens previously unidentified avenues for the application of these materials in molecular electronics and materials science.

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Emerson-King, Jack, Richard C. Knighton, Matthew R. Gyton, and Adrian B. Chaplin. "Rotaxane synthesis exploiting the M(i)/M(iii) redox couple." Dalton Transactions 46, no. 35 (2017): 11645–55. http://dx.doi.org/10.1039/c7dt02648j.

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In the context of advancing the use of metal-based building blocks for the construction of new and interesting mechanically interlocked molecules, we herein describe the preparation of rhodium and iridium containing [2]rotaxanes.

31

Wu, Qiong, Phillip M. Rauscher, Xiaolong Lang, Rudy J. Wojtecki, Juan J. de Pablo, Michael J. A. Hore, and Stuart J. Rowan. "Poly[n]catenanes: Synthesis of molecular interlocked chains." Science 358, no. 6369 (November 30, 2017): 1434–39. http://dx.doi.org/10.1126/science.aap7675.

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As the macromolecular version of mechanically interlocked molecules, mechanically interlocked polymers are promising candidates for the creation of sophisticated molecular machines and smart soft materials. Poly[n]catenanes, where the molecular chains consist solely of interlocked macrocycles, contain one of the highest concentrations of topological bonds. We report, herein, a synthetic approach toward this distinctive polymer architecture in high yield (~75%) via efficient ring closing of rationally designed metallosupramolecular polymers. Light-scattering, mass spectrometric, and nuclear magnetic resonance characterization of fractionated samples support assignment of the high–molar mass product (number-average molar mass ~21.4 kilograms per mole) to a mixture of linear poly[7–26]catenanes, branched poly[13–130]catenanes, and cyclic poly[4–7]catenanes. Increased hydrodynamic radius (in solution) and glass transition temperature (in bulk materials) were observed upon metallation with Zn2+.

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Barin, Gokhan, Ali Coskun, Moustafa M. G. Fouda, and J. Fraser Stoddart. "ChemInform Abstract: Mechanically Interlocked Molecules Assembled by .pi±pi. Recognition." ChemInform 43, no. 32 (July 12, 2012): no. http://dx.doi.org/10.1002/chin.201232277.

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McCarney, Eoin P., William J. McCarthy, June I. Lovitt, and Thorfinnur Gunnlaugsson. "Macrocyclic vs. [2]catenane btp structures: influence of (aryl) substitution on the self templation of btp ligands in macrocyclic synthesis." Organic & Biomolecular Chemistry 19, no. 46 (2021): 10189–200. http://dx.doi.org/10.1039/d1ob02032c.

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The synthesis of four 2,6-bis(1,2,3-triazol-4-yl)pyridine(btp) olefin based ligands 3, 4, 11 and 12 is described and their formation of macrocyclic products using ring closing metatheses (RCM) reactions rather than mechanically interlocked molecules.

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Dixon, Isabelle M., and Gwénaël Rapenne. "Bridging the Gap: Making the Link in Mechanically Interlocked Chiral Molecules." Angewandte Chemie International Edition 49, no. 47 (September 21, 2010): 8792–94. http://dx.doi.org/10.1002/anie.201003298.

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Kim, Kimoon. "ChemInform Abstract: Mechanically Interlocked Molecules Incorporating Cucurbituril and Their Supramolecular Assemblies." ChemInform 33, no. 22 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200222275.

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36

Aricó, Fabio, Theresa Chang, Stuart J. Cantrill, Saeed I. Khan, and J. Fraser Stoddart. "Template-Directed Synthesis of Multiply Mechanically Interlocked Molecules Under Thermodynamic Control." Chemistry - A European Journal 11, no. 16 (August 5, 2005): 4655–66. http://dx.doi.org/10.1002/chem.200500148.

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37

Hood, Thomas M., Samantha Lau, and Adrian B. Chaplin. "Capture of mechanically interlocked molecules by rhodium-mediated terminal alkyne dimerisation." RSC Advances 14, no. 11 (2024): 7740–44. http://dx.doi.org/10.1039/d4ra00566j.

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Barry, Dawn E., David F. Caffrey, and Thorfinnur Gunnlaugsson. "Lanthanide-directed synthesis of luminescent self-assembly supramolecular structures and mechanically bonded systems from acyclic coordinating organic ligands." Chemical Society Reviews 45, no. 11 (2016): 3244–74. http://dx.doi.org/10.1039/c6cs00116e.

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This review focuses on recent developments made in the area of lanthanide directed synthesis/formation of supramolecular self-assembly structures including the formation of complexes/bundles, helicates, MOFs and interlocked molecules.

39

Schröder, Hendrik V., Yi Zhang, and A. James Link. "Dynamic covalent self-assembly of mechanically interlocked molecules solely made from peptides." Nature Chemistry 13, no. 9 (August 23, 2021): 850–57. http://dx.doi.org/10.1038/s41557-021-00770-7.

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Fahrenbach, Albert C., Carson J. Bruns, Dennis Cao, and J. Fraser Stoddart. "Ground-State Thermodynamics of Bistable Redox-Active Donor–Acceptor Mechanically Interlocked Molecules." Accounts of Chemical Research 45, no. 9 (June 28, 2012): 1581–92. http://dx.doi.org/10.1021/ar3000629.

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Fahrenbach, Albert C., Carson J. Bruns, Hao Li, Ali Trabolsi, Ali Coskun, and J. Fraser Stoddart. "Ground-State Kinetics of Bistable Redox-Active Donor–Acceptor Mechanically Interlocked Molecules." Accounts of Chemical Research 47, no. 2 (December 16, 2013): 482–93. http://dx.doi.org/10.1021/ar400161z.

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42

Nieger, M., and F. Vögtle. "Catenanes, Rotaxanes and Knots: From Small Building Blocks to Mechanically Interlocked Molecules." Acta Crystallographica Section A Foundations of Crystallography 56, s1 (August 25, 2000): s323. http://dx.doi.org/10.1107/s0108767300026829.

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Mitra, Raja, Hui Zhu, Stefan Grimme, and Jochen Niemeyer. "Functional Mechanically Interlocked Molecules: Asymmetric Organocatalysis with a Catenated Bifunctional Brønsted Acid." Angewandte Chemie 129, no. 38 (July 4, 2017): 11614–17. http://dx.doi.org/10.1002/ange.201704647.

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La Cognata, Sonia, Ana Miljkovic, Riccardo Mobili, Greta Bergamaschi, and Valeria Amendola. "Organic Cages as Building Blocks for Mechanically Interlocked Molecules: Towards Molecular Machines." ChemPlusChem 85, no. 6 (June 2020): 1145–55. http://dx.doi.org/10.1002/cplu.202000274.

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Mitra, Raja, Hui Zhu, Stefan Grimme, and Jochen Niemeyer. "Functional Mechanically Interlocked Molecules: Asymmetric Organocatalysis with a Catenated Bifunctional Brønsted Acid." Angewandte Chemie International Edition 56, no. 38 (July 4, 2017): 11456–59. http://dx.doi.org/10.1002/anie.201704647.

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Martinez-Cuezva, Alberto, Carmen Lopez-Leonardo, Mateo Alajarin, and Jose Berna. "Stereocontrol in the Synthesis of β-Lactams Arising from the Interlocked Structure of Benzylfumaramide-Based Hydrogen-Bonded [2]Rotaxanes." Synlett 30, no. 08 (January 18, 2019): 893–902. http://dx.doi.org/10.1055/s-0037-1611705.

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Abstract:

β-Lactams are highly valuable compounds due to their antibiotic activity. Among the number of well-established methodologies for building this privileged scaffold, our research group has settled on a novel synthetic approach for their preparation. This Account focuses on our latest progress in the synthesis of these compounds through a novel base-promoted intramolecular cyclization of benzylfumaramide-based rotaxanes. The mechanical bond plays a significant role in the process by activating the cyclization inside the macrocycle void, avoiding the formation of byproducts and fully controlling the diastereoselectivity. Further investigations on this transformation led to the formation of enantioenriched 2-azetidinones. The cyclization of enantiopure interlocked α-methylbenzylfumaramides allows the formation of two new stereogenic centers in the lactamic four-membered ring, one of them a quaternary carbon, keeping the initial configuration of the chiral group of the starting material.1 Introduction1.1 Mechanically Interlocked Molecules and Applications1.2 Chemical Stabilization of the Mechanical Bond2 Literature Methods for 4-exo-trig Ring Closures of Fumaramides for the Synthesis of β-Lactams3 Our First Encounter with Interlocked β-Lactams3.1 An Unexpected Result in Our Laboratory3.2 Finding the Optimal Reaction Conditions3.3 Elucidating the Effects of the Mechanical Bond4 Diastereoselective Synthesis of Interlocked and Non-Interlocked β-Lactams5 Asymmetric Cyclization of Enantiopure Interlocked Fumaramides6 Conclusions

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Xia, Ting, Zhi-Yong Yu, and Han-Yuan Gong. "Pb2+-Containing Metal-Organic Rotaxane Frameworks (MORFs)." Molecules 26, no. 14 (July 13, 2021): 4241. http://dx.doi.org/10.3390/molecules26144241.

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Abstract:

The metal-organic rotaxane framework (MORF) structures with the advantage of mechanically interlocking molecules (MIMs) have attracted intense interest from the chemical community. In this study, a set of MORFs (i.e., MORF-Pb-1 and MORF-Pb-2) are constructed using Pb2+, a tetraimidazolium macrocycle (Texas-sized molecular box; 14+), and aromatic dicarboxylate (p-phthalate dianions (PTADAs; 2) or 2,6-naphthalene dicarboxylate dianions (3)) via a one-pot three-layer diffusion protocol. In particular, an unusual Pb…Pb weak interaction was shown in MORF-Pb-1 (charactered with distance of 3.656 Å).

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Safarnejad Shad, Mastaneh, Pulikkal Veettil Santhini, and Wim Dehaen. "1,2,3-Triazolium macrocycles in supramolecular chemistry." Beilstein Journal of Organic Chemistry 15 (September 12, 2019): 2142–55. http://dx.doi.org/10.3762/bjoc.15.211.

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In this short review, we describe different pathways for synthesizing 1,2,3-triazolium macrocycles and focus on their application in different areas of supramolecular chemistry. The synthesis is mostly relying on the well-known “click reaction” (CuAAC) leading to 1,4-disubstituted 1,2,3-triazoles that then can be quaternized. Applications of triazolium macrocycles thus prepared include receptors for molecular recognition of anionic species, pH sensors, mechanically interlocked molecules, molecular machines, and molecular reactors.

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Brown, Asha, and Paul D. Beer. "Halogen bonding anion recognition." Chemical Communications 52, no. 56 (2016): 8645–58. http://dx.doi.org/10.1039/c6cc03638d.

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Abstract:

The development of solution-based anion receptor molecules which exploit halogen bonding interactions is an emerging area of research. This Feature Article reviews recent advances which have been made in this rapidly developing field, surveying the use of iodoperfluoroarene, haloimidazolium and halotriazole/triazolium halogen-bond-donor motifs in anion receptor design and describing the application of mechanically interlocked rotaxane and catenane frameworks as halogen bonding anion host systems.

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Kolodzeiski, Elena, and Saeed Amirjalayer. "On-the-Fly Training of Atomistic Potentials for Flexible and Mechanically Interlocked Molecules." Journal of Chemical Theory and Computation 17, no. 11 (October 6, 2021): 7010–20. http://dx.doi.org/10.1021/acs.jctc.1c00497.

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