Electrosynthesis and characterization of poly(2-[(E)-2-azulen-1-ylvinyl] thiophene) using polyazulene as model compound

Lete, Cecilia; Esteban, Beatriz Meana; Kvarnström, Carita; Razus, Alexandru C.; Ivaska, Ari

doi:10.1016/j.electacta.2007.04.047

Cited by 21 publications

(32 citation statements)

References 21 publications

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“…This unique electron-donating property can be utilized in solar cell applications. Furthermore, the easy electropolymerization process of Az [11,12] having a relatively low oxidation potential, gives a planar structure to PAz in its conducting form. This results in a rather high electrical conductivity and broad absorbance in the UV and visible wavelength ranges and makes PAz to an attractive material for PV cells.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical polymerization and characterization of a poly(azulene)-TiO2 nanoparticle composite film

et al. 2008

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A poly(azulene)-TiO 2 composite film (PAz-TiO 2 ) was synthesized electrochemically by oxidation of azulene in an electrolyte medium containing TiO 2 nanoparticles. Polymerization was performed under magnetic stirring in an acetonitrile solution containing tetrabutylammonium hexafluorophosphate as the electrolyte salt. Influence of the concentration of TiO 2 in the reaction suspension on the electrochemical and optical properties and on the structure of the composite films was studied by cyclic voltammetry, ex situ Raman and FTIR reflection spectroscopy and in situ UV-vis and FTIR spectroelectrochemical techniques. Morphology of the composite films was studied by Scanning Electron Microscopy and the amount and distribution of the TiO 2 nanoparticles within the polymeric matrix by Inductively Coupled Plasma Mass Spectrometry with laser ablation. Addition of TiO 2 in the reaction suspension had a small catalytic activity for the polymerization of Az. Inclusion of TiO 2 nanoparticles in PAz did not affect the voltammetric behavior or the chemical structure of the formed polymer films. However, a different chain conformation and morphology of the film was formed when synthesized in presence of TiO 2 compared to the plain PAz film. It was also found that the film morphology was more homogeneous when the concentration of TiO 2 was C10 mM in the polymerization solution than films polymerized without any TiO 2 .

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Section: Introductionmentioning

confidence: 99%

Electrochemical polymerization and characterization of a poly(azulene)-TiO2 nanoparticle composite film

et al. 2008

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“…This particular band, however, has a much lower intensity in the spectrum of the PAz film which may mean that in the OAzTiO 2 composite some Az monomer is left. This kind of a broad absorbance in the UV-vis spectral region of the neutral state of PAz has also been reported earlier [20][21][22][23][24][25][26] and can be regarded as a benefit in further development of this kind of material for solar cell applications.…”

Section: In Situ Uv-visible Spectroelectrochemical Characterizationmentioning

confidence: 80%

“…4a shows the CVs of OAz-TiO 2 composite layer when potential cycling was performed to 0.6, 0.9, and 1.0 V starting from -0.4 V. In each CV the third cycle in the respective potential region is shown. p-doping of OAz in the nanoporous TiO 2 layer starting at approximately 0 V in the positive potential scan demonstrates the electron donor property of OAz [21,[28][29][30][31][32]. The current response in the capacitive charging region of OAz-TiO 2 composite layer between -0.4 and 0.35 V depends strongly on the degree of the remaining charge in OAz after oxidation.…”

Section: Polymerization and Cyclic Voltammetric Characterization Of Tmentioning

confidence: 91%

“…The absorption maximum of neutral PAz Fig. 7 The ex situ FTIR spectra of the nanoporous OAz-TiO 2 layer and of the PAz film using a spectrum of ITO/TiO 2 electrode and ITO, respectively, as reference has also been reported by other groups [20][21][22][23][24][25][26][27] to be around 420 nm for both chemically and electrochemically synthesized PAz films. As the absorption maximum of OAz in the composite structure is located at 63 nm higher wavelength it can be concluded that delocalization of the p electrons in OAz in nanoporous TiO 2 is increased.…”

Section: In Situ Uv-visible Spectroelectrochemical Characterizationmentioning

confidence: 93%

“…The absorbance of PAz in the UV and visible spectral regions is also rather broad [20][21][22][23][24][25][26] making PAz an attractive material for applications in solar cells. PAz has also been shown to have electron-donating properties [21,[28][29][30][31][32]. The oxidized form of the fused-ring monomer Az, resonancestabilized azulenylium carbocation, used in this study is very stable [33].…”

Section: Introductionmentioning

confidence: 99%

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Electrochemical preparation of oligo(azulene) on nanoporous TiO2 and characterization of the composite layer

2010

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A nanoporous oligo(azulene)-TiO 2 (OAz-TiO 2 ) composite layer was formed by electrochemical oxidation of azulene (Az) on a nanoporous ITO/TiO 2 electrode. Polymerization was performed in tetrabutylammonium hexafluorophosphate electrolyte salt dissolved in acetonitrile. The electrochemical and optical properties of the composite layer were studied by cyclic voltammetry (CV) and in situ UV-vis spectroelectrochemistry. The chemical and crystalline structure of the layer was studied by FTIR and X-ray diffraction (XRD) spectroscopy techniques and the morphology by Scanning Electron Microscopy. The TiO 2 layer was found to have a catalytic activity on the polymerization of Az. The CV experiments in monomerfree electrolyte solution demonstrated the electron donor property of OAz by its p-doping and the electron accepting property of TiO 2 by the large reduction current in the negative potential region. The FTIR and XRD spectroscopic measurements showed the well-defined anatase structure of TiO 2 with inclusion of OAz. A composite layer was formed rather than a bilayer structure. The in situ UVvis spectroelectrochemical measurements gave evidence of a higher delocalization and easier movement of the p-electrons in the composite layer than in pure poly (azulene).

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Azulene‐Based Molecules, Polymers, and Frameworks for Optoelectronic and Energy Applications

Huang

Zhao

et al. 2020

Small Methods

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has a large dipole moment of 1.08 D. [2] By contrast, naphthalene, which only contains two fused six-membered rings, has a dipole moment of 0 D. Azulene, which was discovered and named by Piesse in 1863, has attracted considerable interest since its discovery in petroleum exploitation. [3] In 1937, Plattner and Pfau published their pioneering report on the synthesis of azulene. [4] However, their method was not practical due to its low azulene yield. In the 1950s, Ziegler and Hafner formulated a highly efficient and practical method for synthesizing azulene and its derivatives. [5] Because azulene is difficult to synthesize and has a low natural abundance, research on azulene-based molecules and materials is less advanced relative to research on its isomer. Direct functionalization of 1-and/ or 3-positions is a common and effective method of producing azulene derivatives. However, direct functionalization of other positions is much harder, e.g., bromination of 6-and 1,3-positions, [6] nucleophilic addition to obtain 6-subsituted azulene, [7] borylation at 2-position, [8] arylation at the 2-position, [9] and so on. The electron distribution in the front-line molecular orbitals (MOs) must usually be considered when functionalizing azulene. Because of resonance delocalization, the oddnumbered position of azulene, which is electron-rich, easily reacts with electrophilic compounds. Among the odd-numbered azulene varieties, 1-and 3-azulene have the highest activity. [10] By Azulene has a considerably larger dipole moment than its isomer naphthalene; it also has unique physicochemical properties, including different reactivities on five-and seven-membered rings, a dark color, a narrow gap between the highest occupied molecular orbital and lowest unoccupied molecular orbital, and stimulus response. Although azulene was discovered more than 100 years ago, the use of azulene-based derivatives can be traced back to five centuries ago. Due to its unusual structure, azulene-based molecules and materials are widely used in various fields. However, studies on azulene-based materials have long been hindered by difficulties in the synthesis. Considerably fewer studies have been conducted on azulene-based derivatives than on naphthalene-based derivatives. This perspective paper mainly introduces recent reports on the synthesis of azulene-based aromatic molecules, conjugated polymers, and coordination polymers, in addition to azulene-based frameworks. The structure-property relationship, optoelectronic applications, and energy-related applications of azulene-based derivatives are reviewed, including their use in near-infrared absorption, organic field-effect transistors, organic solar cells, and microsupercapacitors.

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Electrosynthesis and characterization of poly(2-[(E)-2-azulen-1-ylvinyl] thiophene) using polyazulene as model compound

Cited by 21 publications

References 21 publications

Electrochemical polymerization and characterization of a poly(azulene)-TiO2 nanoparticle composite film

Electrochemical polymerization and characterization of a poly(azulene)-TiO2 nanoparticle composite film

Electrochemical preparation of oligo(azulene) on nanoporous TiO2 and characterization of the composite layer

Azulene‐Based Molecules, Polymers, and Frameworks for Optoelectronic and Energy Applications

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