Synthesis and properties of electroactive aromatic polyimides with methyl- or trifluoromethyl-protecting triphenylamine units

Hsiao, Sheng‐Huei; Lin, Kai-Han

doi:10.1177/0954008316653456

Cited by 11 publications

(10 citation statements)

References 61 publications

(58 reference statements)

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“…Since 2005, Liou's and Hsiao's research groups have contributed a consistent number and various designs of aromatic polyimides containing triphenylamine units as electroactive chromophores. 14,15,17 In general, these polymers found use in diverse technological areas, such as materials for camouflage, 18 stretchable electrochromic skin, 19 eyewear, 20 dimmable windows, 21 smart windows, 22,23 quantitative self-powered electrochromic biosensors, 24 and so on. However, considerable effort is still necessary in developing novel electrochromic materials so as to meet the demands for commercial use.…”

Section: Introductionmentioning

confidence: 99%

Synergetic Effect between Structural Manipulation and Physical Properties toward Perspective Electrochromic n-Type Polyimides

Constantin¹,

Bejan²,

Damaceanu³

2019

Macromolecules

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This work focuses on the development of novel six-membered polyimides, with special concern on the effect of the structural variation on their optoelectronic characteristics and electrochromic performances in electrochromic devices. To this aim, a new aromatic diamine incorporating diphenylamine substituted at the nitrogen atom with a 2-(4-methoxyphenyl)-1,3,4-oxadiazole segment was synthesized and fully characterized. This diamine was used in the one-step high-temperature polycondensation reaction with naphthalene- or perylene-based dianhydrides to produce highly conjugated polyimides. To highlight the effect of structural variation in the diamine segment on the main physical properties, {4-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]-phenyl}-bis-(4-amino-phenyl)-amine was reacted with the same dianhydrides to obtain related polyimides. The obtained polymers displayed high thermal stability, up to 423 °C, and could be processed into thin coatings with morphologies contingent on the macromolecular architecture. With the ability to promote a dual intramolecular charge transfer complex between the diphenylamine/triphenylamine unit and both 1,3,4-oxadiazole in the side chain and naphthylimide or peryleneimide in the main chain, these polyimides experienced challenging photo-optical properties, which were driven by the competition between the electronic effects. The HOMO–LUMO energies evaluated from cyclic voltammetry experiments suggested ambipolar electronic transport characteristics, with a prevalent n-doping capability. Since the oxidation processes of perylene-based polyimides were accompanied by color switching between neutral and oxidized states, preliminary testing in electrochromic devices was carried out. Besides the stable anodic coloring with good response times, the recovery of electrochromic devices was ∼90% after 30 cycles. This excellent stability is mainly promoted by the more extended conjugation provided by the peryleneimide system.

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Section: Introductionmentioning

confidence: 99%

Synergetic Effect between Structural Manipulation and Physical Properties toward Perspective Electrochromic n-Type Polyimides

Constantin¹,

Bejan²,

Damaceanu³

2019

Macromolecules

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“…16 –18 A number of research reports reveal the significance of triphenylamine bearing polymers for hole transport materials, solar cells, electrochromic, and memory applications, due to their film-forming and optoelectronic properties. 19 –26…”

Section: Introductionmentioning

confidence: 99%

Investigation of thermal and fluorescent properties of benzoxazole-linked triphenylamine-based co-polyimides

Iqbal

Siddiqi

Zubair

et al. 2019

High Performance Polymers

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A series of novel fluorescent co-polyimides are obtained by combining N 1-(4-aminophenyl)- N 1-(4-(benzo[ d]oxazol-2-yl) phenyl) benzene-1,4-diamine and 4,4′-oxydianiline with four aromatic anhydride, 3,3′,4,4′-benzophenonetetracarboxylic dianhydride, pyromellitic dianhydride, 4,4′-oxydiphthalic anhydride, and 4,4 ′-(hexafluoroisopropylidene)diphthalic anhydride following conventional polycondensation method. The resultant co-polyimides are characterized by elemental, Fourier transform infrared spectral analysis and gel permeation chromatography. All newly prepared polyimides (PIs) exhibit shallow highest occupied molecular orbital energy levels in the range of −4.47 to −4.98 eV and have reasonable optical bandgaps. The photoluminescence spectral analysis shows blue to green emission in solution form. Thermal and solubility properties reveal that the PIs with pendant 4-(benzo[ d]oxazol-2-yl group linked to triphenylamine unit in polymer backbone impart not only good thermal stability but also appreciable solubility making these new co-polyimides versatile for multipurpose usage.

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“…Very tiny changes in the chemical structures of the reaction monomers may have critical effects on the overall properties of the resulting PI [11][12][13][14]. For instance, introducing flexible links, bulky substituents, fluorinated groups, and copolymerization can improve the processability of polyimides without sacrificing the excellent thermal stability [15][16][17][18][19][20][21][22][23][24]. Among these approaches, introduction of bridged linkages into anhydride structure has been considered to be the most efficient one, which can not only provide broader processing temperature range but also retain thermal stability [25,26].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Semicrystalline Polyimides Containing Bridged Linkages

Chen

2018

International Journal of Polymer Science

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A series of polyimides (PI) containing bridged linkages were prepared successfully through a three-step technique. The results indicated that the glass transition temperature (T g ) of polyimides was affected by flexibility of polymer chain and the intermolecular interactions. ODPA-TPER-based polyimide possesses the lowest T g , which was 214°C. All polyimides had semicrystalline characteristics, and ODPA-TPER-based PI exhibited the lowest melting temperature (T m ) at 316°C. The polyimides had high weight loss temperatures, which indicated that bridged linkages can reduce the softening temperature, meanwhile keeping excellent thermal stability.

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Synthesis and properties of electroactive aromatic polyimides with methyl- or trifluoromethyl-protecting triphenylamine units

Cited by 11 publications

References 61 publications

Synergetic Effect between Structural Manipulation and Physical Properties toward Perspective Electrochromic n-Type Polyimides

Synergetic Effect between Structural Manipulation and Physical Properties toward Perspective Electrochromic n-Type Polyimides

Investigation of thermal and fluorescent properties of benzoxazole-linked triphenylamine-based co-polyimides

Synthesis and Characterization of Semicrystalline Polyimides Containing Bridged Linkages

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