From chains to ladders in co-crystals with 2,3-thiophene-15-crown-5, 2,3-naphtho-15-crown-5, and bis-(18-crown-6)-stilbene constructed by weak hydrogen bonding

Ganin, E. V.; Basok, S. S.; Yavolovskii, A. A.; Botoshansky, Mark; Fonarı, Marina S.

doi:10.1039/c005284c

Cited by 5 publications

(5 citation statements)

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“…Selected bond lengths and dihedral angles are listed in Table 1. As can be seen, the geometrical parameters of N15C5 are very close to the corresponding values previously reported by Ganin et al, 26 suggesting that the geometrical calculations are reliable. The average O-O distance of N15C5 is 2.799 Å (the specific O-O distances are listed in Table S1, ESI †).…”

Section: Geometrical Structuresupporting

confidence: 88%

“…So far, typical 2,3-naphtho crown ethers, such as naphtho-15crown-5 (N15C5), have been widely used in the field of electrochemistry, and some of their coordinating behaviors in solution have been studied by cyclic voltammetry and electrospray ionization mass spectrometry methods. [25][26][27][28][29] However, presently, only a few reports describe NLO studies on the crown ethers, let alone investigate their use in the NLO-based detection of cations. 30,31 Inspired by our previous papers [32][33][34][35][36][37][38] on the NLO switching and the strong complex formation ability of crown compounds, the crown ether compounds formed by N15C5 with group I alkali metal cations (Li + , Na + , K + ), group II alkali metal cations (Be 2+ , Mg 2+ , Ca 2+ ) and transition metal cations (Co 2+ , Ni 2+ , Cu 2+ ) (Fig.…”

Section: Introductionmentioning

confidence: 99%

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Variational first hyperpolarizabilities of 2,3-naphtho-15-crown-5 ether derivatives with cation-complexing: a potential and selective cation detector

Wang

Hong

et al. 2016

Phys. Chem. Chem. Phys.

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Crown ethers, as a kind of heterocycle, have been the subject of great interest over recent decades due to their selective capability to bind to metal cations. The use of a constant crown ether, such as naphtho-15-crown-5 (N15C5), and varied metal cations (Li, Na, K, Be, Mg, Ca, Co, Ni, Cu) makes it possible to determine the contributions of the metal cations to nonlinear optical (NLO) responses and to design an appropriate NLO-based cation detector. N15C5 and its metal cation derivatives have been systematically investigated by density functional theory. It is found that the dependency of the first hyperpolarizability relies on the metal cation, especially for transition metals. The decrease of the first hyperpolarizabilities for alkali metal cation derivatives is due to their relatively low oscillator strengths, whereas the significant increase of the first hyperpolarizabilities for transition metal cation derivatives can be further illustrated by their low transition energies, large amplitudes and separate distributions of first hyperpolarizability density. Thus, the alkali metal and transition metal cations are distinguishable and the transition metal cations are easier to detect by utilizing the variations in NLO responses.

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Section: Geometrical Structuresupporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Variational first hyperpolarizabilities of 2,3-naphtho-15-crown-5 ether derivatives with cation-complexing: a potential and selective cation detector

Wang

Hong

et al. 2016

Phys. Chem. Chem. Phys.

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“…Although C(75)‐PAEK also has an amorphous structure, its increased crown ether content apparently lowers the solubility of this polymer. The solubility change can be explained by stacking of crown ether units in the main chain . The phenyl rings in dibenzo‐18‐crown‐6 may favor π‐stacking interactions .…”

Section: Resultsmentioning

confidence: 99%

“…The solubility change can be explained by stacking of crown ether units in the main chain . The phenyl rings in dibenzo‐18‐crown‐6 may favor π‐stacking interactions . The sulfonated PAEK and C‐PAEK were only soluble in the aforementioned polar aprotic solvents.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of poly(arylene ether ketone)s bearing skeletal crown ether units for cation exchange membranes

Zoetebier

Taş

Vancso

et al. 2015

J. Polym. Sci., Part A: Polym. Chem.

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Poly(arylene ether ketone)s (PAEKs) are the most commonly known high‐performance materials used for ion exchange and fuel cell membranes. Described here is the design of novel sulfonated PAEKs (SPAEKs) and nonsulfonated PAEKs containing crown ether units in the main chain, which can be used in sensing applications and ion‐selective membranes. To this end, 4,4′(5′)‐di(hydroxybenzo)‐18‐crown‐6 was synthesized and used as monomer in a step growth polymerization to form crown ether‐containing PAEKs and SPAEKs. The successful synthesis of PAEKs containing 18‐crown‐6 and sulfonate groups was confirmed by gel permeation chromatography, Fourier transform infrared spectroscopy, and nuclear magnetic resonance spectroscopy. Membranes are fabricated from the sulfonated polymers. Potassium ion transport properties of the SPAEK and crown ether‐containing SPAEK membranes are assessed by diffusion dialysis. Potassium ion diffusion in the crown ether‐containing SPAEK membranes is almost four times lower than K+ diffusion in the native polymer membranes, without crown ether. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2786–2793

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“…57,59 The sulfonated PAEK and CPAEK were only soluble in the aforementioned polar aprotic solvents. PVA-based poly(crown ether) showed similar effects for potassium picrate, with a two-fold decrease in permeability due to strong crown ether-cation interactions.…”

Section: -58mentioning

confidence: 99%

Functional macromolecules and smart polymer networks for ion separation, reduction and delivery

Zoetebier

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This thesis is part of NanoNextNL, a micro and nanotechnology innovation consortium of the Government of the Netherlands and 130 partners from academia and industry. More information on www.nanonextnl.nl. IntroductionSince decades, nature has been an inspiration for the fields of polymer chemistry and materials science. To date, it remains a challenge to mimic natural systems to attain their desired properties. 1-2Traditional polymers can generally meet particular parameters one at a time. For example mechanical properties can be improved but often without enhancement of other materials parameters. The same also holds for other properties. In contrast, natural polymers developed during genesis often possess a set of properties which have been simultaneously optimized to achieve a given task. In the field of materials science, chemical properties are combined with structural and surface properties, mimicking, for instance, the gecko foot and the lotus leaf.Self-assembly at different length scales, one of the key elements that nature presents to us, provides simple building blocks for otherwise difficult to achieve structures, which are preferentially assembled through supramolecular chemistry. 5The dynamic, stimuli-responsive character of these interactions provide adaptive reversible connections in many molecular processes and materials. For example, molecular recognition processes can trigger biological responses, awakening the field of biosensors and actuators. 6 The Mimosa pudica, a plant which folds its leafs upon receiving a stimulus, is another fascinating example of the responsiveness of natural systems. Upon a touch or air movement, a release of chemicals is triggered which causes water removal and subsequent cell collapse, giving rise to the folding of its leafs. 7These are just a few examples of the materials and objects developed and evolved over time by nature. Biomimetics brings together scientists from different fields in an attempt to create e.g., molecular-scale devices, nanomedicine, actuators, selfChapter 1 3 assembling and self-healing materials and tools for molecular sensing and recognition.In the related fields of stimulus responsive hydrogels and ionic polymer-metal composite actuators, research is focused on achieving comparable responses with synthetic materials. In this thesis attention will be paid to hydrogels and "unconventional" polymers that incorporate inorganic elements in their main chain. Concept of this thesisThe concept of the research described in this thesis is centered around the synthesis, characterization and function of novel organometallic polyanions, polycations, and their corresponding hydrogels and the exploration of the use of these redox-responsive water-soluble or water-swellable materials in metal nanoparticle fabrication and transfection. In addition, crown ether-functionalized aromatic polymers and organometallic polymers will be employed for ion separation and sensing.Chapter 2 summarizes the field of stimulus responsive polymers, focusing on redox res...

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From chains to ladders in co-crystals with 2,3-thiophene-15-crown-5, 2,3-naphtho-15-crown-5, and bis-(18-crown-6)-stilbene constructed by weak hydrogen bonding

Cited by 5 publications

References 64 publications

Variational first hyperpolarizabilities of 2,3-naphtho-15-crown-5 ether derivatives with cation-complexing: a potential and selective cation detector

Variational first hyperpolarizabilities of 2,3-naphtho-15-crown-5 ether derivatives with cation-complexing: a potential and selective cation detector

Synthesis of poly(arylene ether ketone)s bearing skeletal crown ether units for cation exchange membranes

Functional macromolecules and smart polymer networks for ion separation, reduction and delivery

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