Electrochromic devices based on surface-confined Prussian blue or Ruthenium purple and aqueous solution-phase di-n-heptyl viologen

Mortimer, Roger J.; Varley, Thomas S.

doi:10.1016/j.solmat.2012.11.008

Cited by 16 publications

(19 citation statements)

References 14 publications

(25 reference statements)

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“…1 H NMR (300.18 MHz, DMSO-d 6 ): δ 12.27 (s, 1H, OH), 8.78 (m, 1H, H3), 8.74 (m, 1H, H3′), 8.59 (d, 3 J = 7.9 Hz, 1H, H6), 8.52 (d, 3 J = 7.9 Hz, 1H, H6′), 8.11 (td, 3 J = 7.8 Hz, 4 J = 1.7 Hz, 1H, H5), 8.03 (td, 3 J = 7.7 Hz, 4 J = 1.8 Hz, 1H, H5′), 7.69 (ddd, 3 J = 4.8 Hz, 4 J = 1.1 Hz, 1H, H4), 7.56 (ddd, 3 J = 4.7 Hz, 4 J = 1.1 Hz, 1H, H4′), 7.28 (s, 1H, H9) ppm. 13 Synthesis of 4-Chloro-2,6-bis(2-pyridyl)pyrimidine (8). 4-Hydroxy-2,6-bis(2-pyridyl)pyrimidine 7 (0.88 g, 3.52 mmol) was added slowly to the freshly distilled thionyl chloride (30 mL) under an inert atmosphere.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…1 H NMR (300.18 MHz, CDCl 3 ): δ 8.89 (m, 1H, H3), 8.74 (m, 1H, H3′), 8.68 (d, 3 J = 7.9 Hz, 1H, H6), 8.62 (d, 3 J = 8.0 Hz, 1H, H6′), 8.44 (s, 1H, H9), 7.90 (m, 2H, H5, H5′), 7.45 (m, 2H, H4, H4′) ppm. 13 C NMR (75.48 MHz, CDCl 3 ): δ 165.17 Synthesis of 2-Pyridalacetophenone (11). 31 Acetophenone 10 (3.85 g, 32 mmol) and DBU 3 (4.79 mL, 32 mmol) were added to a solution of 2-pyridinecarboxaldehyde 2 (6.08 mL, 64 mmol) in anhydrous tetrahydrofuran (80 mL).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Green-to-Red Electrochromic Fe(II) Metallo-Supramolecular Polyelectrolytes Self-Assembled from Fluorescent 2,6-Bis(2-pyridyl)pyrimidine Bithiophene

et al. 2017

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The structure and properties of metallo-supramolecular polyelectrolytes (MEPEs) self-assembled from rigid 2,6-bis(2-pyridyl)pyrimidine and the metal ions Fe and Co are presented. While FeL1-MEPE (L1 = 1,4-bis[2,6-bis(2-pyridyl)pyrimidin-4-yl]benzene) is deep blue, FeL2- and CoL2-MEPE (L2 = 5,5'-bis[2,6-bis(2-pyridyl)pyrimidin-4-yl]-2,2'-bithiophene) are intense green and red in color, respectively. These novel MEPEs display a high extinction coefficient and solvatochromism. Ligand L2 shows a high absolute fluorescence quantum yield (Φ = 82%). Viscosity and static light-scattering measurements reveal that the molar masses of these MEPEs are in the range of 1 × 10 g/mol under the current experimental conditions. In water, FeL1-MEPE forms a viscous gel at 20 °C (c = 8 mM). Thin films of high optical quality are fabricated by dip coating on transparent conducting indium tin oxide (ITO) glass substrate. Optical, electrochemical, and electrochromic properties of the obtained MEPEs are presented. Green to red and blue to colorless electrochromism is observed for FeL2-MEPE and FeL1-MEPE, respectively. The results show that the electrochromic properties are affected by the ligand topology. The Fe-MEPEs show a reversible redox behavior of the Fe/Fe couple at 0.86 and 0.82 V versus Fc/Fc and display an excellent redox cycle stability under switching conditions. FeL2-MEPE in its oxidized state exhibits a broad absorption band covering the near-IR region (ca. 1500 nm) due to the ligand-to-metal charge transfer transition originating due to charge delocalization in the bithiophene spacer.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Green-to-Red Electrochromic Fe(II) Metallo-Supramolecular Polyelectrolytes Self-Assembled from Fluorescent 2,6-Bis(2-pyridyl)pyrimidine Bithiophene

et al. 2017

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“…When comparing electrochromic materials derived from metal oxides 1 with molecular organic [2][3][4] and polymeric 5 electrochromes, the latter stand out for the broad array of colours that can switch to highly transmissive states. Due to their solubility allowing them to be processed via spin, [6][7][8] spray, 9,10 blade, 11 and slot-die 12 coating along with inkjet printing, 11,13 fully conjugated electrochromic polymers (ECPs) provide a full palette of colours from which to develop devices.…”

Section: Introductionmentioning

confidence: 99%

Tuning the painter's palette: subtle steric effects on spectra and colour in conjugated electrochromic polymers

Kerszulis

Johnson

Kuepfert³

et al. 2015

J. Mater. Chem. C

137

129

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“…11 In another report, electrochromic devices with aqueous solution phase di-heptyl viologen (N,N 0 -diheptyl-4,4 0bipyridylium) as the cathodic electrochrome and surface conned Prussian blue or Ruthenium purple as the anodic electrochrome were fabricated and in situ spectroelectrochemistry and color measurement were studied. 12,13 In yet another study, a poly(butyl viologen) and Prussian blue based electrochromic device was fabricated using a solid electrolyte based on succinonitrile and a large coloration efficiency was obtained. 14 In another study, layer-by-layer (LbL) self-assembled multilayer lms were fabricated using a perylenediimide-viologen dyad and poly(3,4-ethylenedioxythiophene)-poly-(styrenesulfonate) (PEDOT:PSS) and a three stage color change from red to blue to violet was attained.…”

Section: Introductionmentioning

confidence: 99%

A new organo-inorganic hybrid of poly(cyclotriphosphazene-4,4′-bipyridinium)chloride with a large electrochromic contrast

Sydam

Deepa

2013

J. Mater. Chem. C

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A new organo-inorganic hybrid electrochromic material poly(cyclotriphosphazene-4,4 0 -bipyridinium)chloride salt was synthesized wherein each phosphorus atom in the triphosphazene core is linked by diquaternized 4,4 0 -bipyridyls (PPBP). The electrochrome was characterized by 31 P nuclear magnetic resonance, Fourier transform infrared spectroscopy and X-ray photoelectron spectroscopy (XPS). XPS confirmed the formation of P-N + and P-N linkages in the PPBP and the conversion of covalently bound Cl to ionic Cl À species. The transparent PPBP material undergoes three reversible one electron-transfer reactions to yield a radical cation insoluble film which first acquires a purple hue and then turns deep blue. Electrochromic devices were constructed with the PPBP hybrid dissolved in a highly conductive, thermally stable and electrochemically inert ionic liquid based gel electrolyte and a Prussian blue (PB) layer as the anode. The PPBP-PB device showed an extremely large coloration efficiency of 504 cm 2 C À1 , an exceptionally high transmission modulation of 70.5% at 590 nm, one among the highest reported contrasts in organic electrochromics, a large reflectance contrast of 59.2% at 545 nm and fast switching kinetics. The device was durable as it retained 96.2% of its original transmission after 1000 color-bleach cycles, thus exemplifying its use for both reflective and transmissive electrochromic applications.Electrochemical impedance studies revealed charge transfer to be a less resistive process during reduction relative to oxidation which cumulatively ensues in shorter coloration times. Our studies demonstrate the yet untapped potential of the inorganic (PNCl 2 ) 3 in steering the synthesis of new organo-inorganic hybrid materials, capable of undergoing facile redox phenomena, manifesting in unequalled functional properties and thereby offering opportunities to use this trimer for preparing a whole gamut of new high performance electroactive compounds.

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Electrochromic devices based on surface-confined Prussian blue or Ruthenium purple and aqueous solution-phase di-n-heptyl viologen

Cited by 16 publications

References 14 publications

Green-to-Red Electrochromic Fe(II) Metallo-Supramolecular Polyelectrolytes Self-Assembled from Fluorescent 2,6-Bis(2-pyridyl)pyrimidine Bithiophene

Green-to-Red Electrochromic Fe(II) Metallo-Supramolecular Polyelectrolytes Self-Assembled from Fluorescent 2,6-Bis(2-pyridyl)pyrimidine Bithiophene

Tuning the painter's palette: subtle steric effects on spectra and colour in conjugated electrochromic polymers

A new organo-inorganic hybrid of poly(cyclotriphosphazene-4,4′-bipyridinium)chloride with a large electrochromic contrast

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