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. Among all these molecular entities, rotaxanes have a special locale and many research groups over the globe have contributed to their current niche in supramolecular chemistry. From refinements for better yielding synthetic strategies to their application oriented designs, this field has come a long way and is well inclined for further developments. In this review, we aim to document the contemporary developments in the synthesis of phenanthroline (phen) based rotaxanes. In addition to providing a comprehensive account of various subtypes of these rotaxanes and their stitching strategies, their applications, wherever discernible, will be duely highlighted.
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http://dx.doi.org/10.1039/d2ra01318e | DOI Listing |
Angew Chem Int Ed Engl
December 2024
Hangzhou Normal University, College of Material, Chemistry and Chemical Engineering, 2318 Yuhangtang Rd, 311121, Hangzhou, CHINA.
As a unique property of the interlocked structures, rotaxane allows for intramolecular motions between its wheel and axle components. Introduction of rotaxanes into polymers can endow them with distinctive macroscopic features and outstanding mechanical properties. Here, we prepare a copillar[5]arene with a hydroxyl and an amino-group on each end, which can spontaneously form a pseudo[1]rotaxane through intramolecular hydrogen bonds.
View Article and Find Full Text PDFBeilstein J Org Chem
November 2024
Institute for Chemical Technology and Polymer Chemistry (ITCP), Karlsruhe Institute of Technology (KIT), 76131 Karlsruhe, Germany.
Owing to their dynamic natures, rotaxane-based polymers are attractive motifs for developing stimuli-responsive materials. However, the accurate control of the rotaxane structure, which can be achieved via multistep synthesis, is key to utilizing the material. Concurrently, implementing a scale-up synthesis procedure to exploit the application potential of rotaxane-based polymers induces structural ambiguities, thereby presenting a significant trade-off between realizing inexpensive production and defined structures.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2024
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular and Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, China.
Starting from AIEgen-functionalized chiral [2]rotaxane building block, we have successfully synthesized a new class of chiral rotaxane-branched dendrimers through controllable divergent strategy for the first time, based on which novel chiral artificial light-harvesting systems (LHSs) were successfully constructed in aqueous phase by sequentially introducing achiral donor and acceptor. More importantly, accompanied by the two-step Förster resonance energy transfer (FRET) process in the resultant artificial LHSs, the sequentially amplified circularly polarized luminescence (CPL) performances were achieved, highlighting that the chiral rotaxane-branched dendrimers could serve as excellent relay for both energy transfer and chirality transmission. Impressively, compared with the sole chiral rotaxane-branched dendrimers, the dissymmetry factors (g) values of the resultant artificial LHSs were amplified by one order of magnitude up to 0.
View Article and Find Full Text PDFChem Sci
December 2024
Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín Vavrečkova 5669 760 01 Zlín Czech Republic
Rotaxanes can be regarded as storage systems for their wheel components, which broadens their application potential as a complement to the supramolecular systems that retain a mechanically interlocked structure. However, utilising rotaxanes in this way requires a method to release the wheel while preserving the integrity of all molecular constituents. Herein, we present simple rotaxanes based on cucurbit[6]uril (CB6), with an axis equipped with an additional binding motif that enables the binding of another macrocycle, cucurbit[7]uril (CB7).
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, 5230 Odense M, Denmark.
Incorporating a steric barrier between the two stations in a bistable [2]rotaxane based on monopyrrolotetrathiafulvalene and cyclobis(paraquat--phenylene) allows the high-energy metastable-state co-conformation to be physically isolated following a single redox cycle, thus making it possible to store energy (4.4 J L) and to follow its interconversion back to the ground-state co-conformation.
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