Untying the Photophysics of Quinolinium‐Based Molecular Knots and Links

Caprice, Kenji; Aster, Alexander; Kumpulainen, Tatu

doi:10.1002/chem.201904456

Cited by 20 publications

(15 citation statements)

References 77 publications

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“…This acid/base switching behavior inspired Cougnon, Kumpulainen, and co‐workers to exploit the trefoil knot 31 6+ and the Solomon link 29 8+ in the development of molecular switches . As discussed earlier, the protonated forms of 31 6+ and Solomon link 29 8+ are able to recognize two Br − anions and four water molecules, respectively, through the formation of hydrogen bonds between these guests and the hydrazone NH protons.…”

Section: Self‐assembly Based On Acylhydrazone Formation In Watermentioning

confidence: 85%

Self‐Assembly in Water with N‐Substituted Imines

Jiao

Zhang

et al. 2020

Angew Chem Int Ed

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Imine synthesis has enjoyed along history as the dynamic covalent reaction of choice for the construction of purely covalent molecular architectures.Ino rganic solvents,t he formation of imine bonds is reversible but leads to thermodynamically stable products.I nt he presence of water,however,imine bonds are labile,afact whichlimits their utility as mediators of self-assembly in aqueous and biological media. In this Review,wediscuss water-compatible dynamic covalent bonds based on N-substituted imine derivatives,n amely hydrazones and oximes,f or the self-assembly of metal-free organic architectures with well-defined structures.The reasons why hydrazones and oximes are more robust in water than their parent imines are explained. Recent progress in the self-assembly,characterization, and design principles of avariety of complex molecules including macrocycles,c ages,catenanes,a nd knots in aqueous media is highlighted. Emerging applications for these molecules,including guest recognition and separations, are also discussed. From the Contents 1. Introduction 18351 2. Mechanism for the Formation of Imines and N-Substituted Derivatives 18353 3. N-Substituted Imines in the Syntheses of Dynamic Combinatorial Libraries and Polymeric Products as well as Bioconjugation 18354 4. Self-Assembly Based on the Formation of Imines in Water 18355

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Section: Self‐assembly Based On Acylhydrazone Formation In Watermentioning

confidence: 85%

Self‐Assembly in Water with N‐Substituted Imines

Jiao

Zhang

et al. 2020

Angew Chem Int Ed

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“…The nonbasic anions (Br − , NO 3 − , ClO 4 − ) did not change the absorption spectra, while the basic anions led to an increasing peak at 420 nm with increasing PL intensity ( Figures S7 and S8). According to the previous literature, the pK a of acyl hydrazone N-H ranges from 8.8 to 11.3 in aqueous solution [62]. The pH value of bQH solution (5.0 × 10 −6 M in DMSO) was measured to be 8.0 using a pH meter.…”

Section: Resultsmentioning

confidence: 99%

Solid-State Emissive Metallo-Supramolecular Assemblies of Quinoline-Based Acyl Hydrazone

Cho

Kim

et al. 2020

Sensors

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Development of fluorescence-based sensory materials for metal elements is currently in the mainstream of research due to the simplicity and usability of fluorescence as a method of detection. Herein, we report a novel “bis”-quinoline-based acyl hydrazone—named bQH that could be synthesized by a facile, low-cost method through simple condensation of hydrazide with an aldehyde. This acyl hydrazone showed emissive properties through Zn selective binding, especially in its solid-state, as shown by experiments such as UV–Vis, photoluminescence (PL), nuclear magnetic resonance (NMR), and inductively-coupled plasma-optical emission spectroscopies (ICP-OES), and energy-dispersive X-ray spectroscopy (EDS) mapping. The binding modes in which bQH coordinates to Zn2+ was proved to consist of two modes, 1:1 and 1:2 (bQH:Zn2+), where the binding mode was controlled by the Zn2+ ion content. Under the 1:1 binding mode, bQH-Zn2+ complexes formed a polymeric array through the metallo-supramolecular assembly. The resulting bQH-Zn2+ complex maintained its fluorescence in solid-state and exhibited excellent fluorescence intensity as compared to the previously reported quinoline-based acyl hydrazone derivative (mQH).

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“…Tying strands, which will result in an increase in local bulk, while introducing topological chirality into molecules will become a center stage in chemistry. Recently, empirical investigations 45,209,215,247 have been conducted to unravel how tightness and chiral expression can be influenced by the topology of a molecule. Leigh 46 has shown that the chiral expression in a nanoscale knot can invert reversibly the chiral organization of cholesteric liquid crystals on the centimeter scale, i.e., chiral amplification can span over seven orders of scalar magnitude.…”

Section: Discussionmentioning

confidence: 99%

The Rise and Promise of Molecular Nanotopology

et al. 2021

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Molecular nanotopology-a term we coined recently-is a rapidly developing field of research that is emerging out of the confluence of chemical topology with the mechanical bond. By focusing on the increased research activities in this field, it is clear that a new discipline is ready to receive recognition in its own right. In this Mini-Review, we address the historical development of chemical topology and describe how the rational design and practical synthesis of molecular links and knots with mechanical bonds, together with interwoven extended frameworks, have led to the rapid establishment of molecular nanotopology as a discipline. Representative examples are highlighted in order to offer the reader an extensive overview of ongoing research. We spotlight the major challenges facing chemists and materials scientists and provide some pointers as to how molecular nanotopology is going to develop in the years ahead.

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Untying the Photophysics of Quinolinium‐Based Molecular Knots and Links

Cited by 20 publications

References 77 publications

Self‐Assembly in Water with N‐Substituted Imines

Self‐Assembly in Water with N‐Substituted Imines

Solid-State Emissive Metallo-Supramolecular Assemblies of Quinoline-Based Acyl Hydrazone

The Rise and Promise of Molecular Nanotopology

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