Polyiminofluorene with conjugated benzimidazolylpyridine substituent groups: optical properties, ionochromism and coordinative self-assembly into electrochromic films

Cheng, Kalie; Tieke, Bernd

doi:10.1039/c4ra03969f

Cited by 10 publications

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“…Using this approach electrochromic and photoluminescent films were recently described by our group . It was shown that a structural variation of polymer, metal ions, and counterions can be used to vary and optimize the functional properties of the films …”

Section: Introductionmentioning

confidence: 99%

“…As a continuation of our previous studies on coordination polymer films and on the transport of ions and molecules across polyelectrolyte multilayer films, we now became interested in the study of materials transport across coordination polymer films. Motivation for the present work also came from the generally growing interest in metallopolymers, metallo‐supramolecular polymers, and metal organic frameworks and their use as active materials in membrane applications .…”

Section: Introductionmentioning

confidence: 99%

“…[14][15][16] It (2 of 16) 1700052 was shown that a structural variation of polymer, metal ions, and counterions can be used to vary and optimize the functional properties of the films. [15,[17][18][19][20] As a continuation of our previous studies on coordination polymer films [14][15][16][17][18][19][20] and on the transport of ions and molecules across polyelectrolyte multilayer films, [21,22] we now became interested in the study of materials transport across coordination polymer films. Motivation for the present work also came from the generally growing interest in metallopolymers, metallo-supramolecular polymers, and metal organic frameworks and their use as active materials in membrane applications.…”

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confidence: 99%

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Coordinative Layer-by-Layer Assembly of Thin Films Based on Metal Ion Complexes of Ligand-Substituted Polystyrene Copolymers and Their Use as Separation Membranes

Krieger

Tieke

2017

Macromol. Chem. Phys.

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Polystyrene copolymers containing either 4′‐vinyl‐2,2′:6′,2″‐terpyridine (P1) or 2,6‐bis(1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)pyridin‐4‐yloxy)‐methacrylate (P2) as comonomers are prepared and studied on metal ion coordination in solution and coordinative sequential assembly of films and membranes. Permeation and separation of ions and neutral aromatic molecules across the membranes are investigated. UV–vis titration of P1 with zinc acetate in chloroform/methanol (25:1) indicates formation of 2:1 ligand:metal bis‐complexes, while titration of P2 led to 1:1 monocomplexes. It is demonstrated that coordinative interactions between the ligand groups and metal ions such as Zn(II) or Cu(II) can be used for layer‐by‐layer assembly of ultrathin films on solid quartz supports and porous supporting membranes. Formation of coordination polymer assemblies is characterized using UV‐spectroscopy, quartz crystal microbalance measurements, scanning electron microscopy, and thickness measurements. Coordinative films prepared on porous polyacrylonitrile/polyethylene terephthalate supporting membranes exhibit a selective transport of ions and small molecules. Ion transport in aqueous and alcoholic solution is controlled by a sieving effect and by electrostatic rejection at the ligand–metal ion complexes in the membrane. The transport of organic aromatic molecules is only controlled by the sieving effect. Separation factors α(NaCl/BaCl2) up to 4.2 and α(naphthalene/perylene) up to 4.8 are found.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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Coordinative Layer-by-Layer Assembly of Thin Films Based on Metal Ion Complexes of Ligand-Substituted Polystyrene Copolymers and Their Use as Separation Membranes

Krieger

Tieke

2017

Macromol. Chem. Phys.

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“…[12][13][14] The absorption wavelength of transition metal complexes signicantly depends on the redox state of their building blocks and their properties can be modied by changing the ligands or metal ions. 15 So far, mainly transition metal complexes with oligopyridines or phthalocyanines were examined as electrochromic materials, while electrochromic properties of transition metal complexes with hydrazones have not been widely investigated.…”

Section: Introductionmentioning

confidence: 99%

Electrochromism and electrochemical properties of complexes of transition metal ions with benzimidazole-based ligand

et al. 2017

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“…S1 †). 18,19 Subsequently, this ligand was coupled to dodecanoic acid and bis-carboxylic acid functionalised telechelic poly(ethylene-co- † Electronic supplementary information (ESI) available: A comprehensive account of all experimental details, including synthetic procedures, analytical data, and NMR spectra of all novel compounds is provided. See…”

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Solid-state sensors based on Eu³⁺-containing supramolecular polymers with luminescence colour switching capability

et al. 2018

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aPolymers that exhibit changes of their luminescence colour in response to external stimuli are attractive candidates for sensing systems. We herein report the preparation of europium-based metallosupramolecular polymers, which can be processed into films and coatings that display readily detectable luminescence colour changes in response to various types of analytes. 14 These low-molecular weight solvent-based sensory systems demonstrate the potential benefits of luminescence colour changes, and similar responses were also achieved with metallosupramolecular polymer (MSP) networks that feature combinations of transition or lanthanide metal ions due to a selective quenching of some of the metal-based emission. 15,16 A direct monitoring of the disassembly with a potential increase in sensitivity may be achieved by employing ligands that feature a distinct emission in the visible range, which has, to the best of our knowledge, not been explored in polymeric solid-state materials so far. We herein report a lanthanide-based MSP system that features a distinct and clearly visible emission colour change due to the vastly different emission characteristics of the metalligand complex, and the telechelic, ligand-carrying macromonomer. Red-light emitting MSP films are obtained upon assembling the macromonomer with europium perchlorate and a clearly visible luminescence colour change is observed in response to different stimuli such as heat, exposure to solvents, or other analytes that disrupt or alter the metal-ligand complexes. The distinct colour change constitutes a visually detectable signal that indicates exposure to the various analytes and may allow for an in situ optical monitoring. MetalThe basis of the approach used in our study are tridentate Mebip ligands, which are known to act as efficient "antennas" for lanthanide ions.17 However, Mebip itself does not fluoresce in the visible range. To shift the fluorescence of this motif into the visible range, an extension of the conjugated π-system was pursued. Thus, 2,6-bis(1′-methylbenzimidazolyl)-4-bromopyridine was prepared following literature procedures and its coupling to 4-ethynylaniline under Sonogashira conditions yielded the desired π-extended Mebip derivative (Fig. S1 †). 18,19 Subsequently, this ligand was coupled to dodecanoic acid and bis-carboxylic acid functionalised telechelic poly(ethylene-co- † Electronic supplementary information (ESI) available: A comprehensive account of all experimental details, including synthetic procedures, analytical data, and NMR spectra of all novel compounds is provided. See

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Polyiminofluorene with conjugated benzimidazolylpyridine substituent groups: optical properties, ionochromism and coordinative self-assembly into electrochromic films

Abstract: A new polyiminofluorene with conjugated bis(methylbenzimidazolyl)pyridine ligands in the side chain has been synthesized. Ionochromism of the polymer and electrochromic behaviour after coordinative layer-by-layer assembly into ultrathin films are described.

Cited by 10 publications

References 35 publications

Coordinative Layer-by-Layer Assembly of Thin Films Based on Metal Ion Complexes of Ligand-Substituted Polystyrene Copolymers and Their Use as Separation Membranes

Coordinative Layer-by-Layer Assembly of Thin Films Based on Metal Ion Complexes of Ligand-Substituted Polystyrene Copolymers and Their Use as Separation Membranes

Electrochromism and electrochemical properties of complexes of transition metal ions with benzimidazole-based ligand

Solid-state sensors based on Eu³⁺-containing supramolecular polymers with luminescence colour switching capability

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Polyiminofluorene with conjugated benzimidazolylpyridine substituent groups: optical properties, ionochromism and coordinative self-assembly into electrochromic films

Abstract: A new polyiminofluorene with conjugated bis(methylbenzimidazolyl)pyridine ligands in the side chain has been synthesized. Ionochromism of the polymer and electrochromic behaviour after coordinative layer-by-layer assembly into ultrathin films are described.

Cited by 10 publications

References 35 publications

Coordinative Layer-by-Layer Assembly of Thin Films Based on Metal Ion Complexes of Ligand-Substituted Polystyrene Copolymers and Their Use as Separation Membranes

Coordinative Layer-by-Layer Assembly of Thin Films Based on Metal Ion Complexes of Ligand-Substituted Polystyrene Copolymers and Their Use as Separation Membranes

Electrochromism and electrochemical properties of complexes of transition metal ions with benzimidazole-based ligand

Solid-state sensors based on Eu3+-containing supramolecular polymers with luminescence colour switching capability

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Solid-state sensors based on Eu³⁺-containing supramolecular polymers with luminescence colour switching capability