Synthesis and properties of high‐performance functional polyimides containing rigid nonplanar conjugated tetraphenylethylene moieties

Liu, Yiwu; Zhang, Yi; Lan, Qi; Qin, Zexin; Liu, Siwei; Zhao, Cunyuan; Chi, Zhenguo; Xu, Jiarui

doi:10.1002/pola.26498

Cited by 57 publications

(27 citation statements)

References 56 publications

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“…The aggregation enhanced emission (AEE) may be caused due to restriction of intramolecular rotation (RIR) . Thus, the RIR is effectively restricting the nonradiative decay channels leading to enhanced emission in THF/water mixture.…”

Section: Resultssupporting

confidence: 79%

Conjugated polymers with carbazole, fluorene, and ethylene dioxythiophene in the main chain and a pendant cyano group: Synthesis, photophysical, and electrochemical studies

Anand

Ramachandran

Dhamodharan

2016

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

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Six new conjugated polymers comprising of carbazole, fluorene, and ethylene dioxythiophene (EDOT) moieties along the backbone with a pendant cyano group attached to the ethylene moiety have been designed and synthesized via Sonogashira coupling polymerization reaction. Optical and electrochemical characterizations have shown that the energy band gaps lie within the range of 2.35–2.44 eV. Additionally, the presence of carbazole and EDOT makes these polymers better hole transporting materials, which is reflected from their low oxidation potential peaks (0.55–1.11 V) in cyclic voltammograms. Furthermore, the aggregation enhanced emission (AEE) phenomenon resulted in a 2.6‐fold increase in fluorescence intensity in a 90:10 THF/water mixture in comparison to pristine THF. The AEE properties were further verified by DLS (dynamic light scattering) experiment and SEM (scanning electron microscopy) studies. Polymers in solution as well as in polystyrene matrix emit in the green region (quantum yield in solution state Φf =41–43%) with CIE values (0.25–0.36, 0.52–0.57). Excellent thermal stability is observed for the new polymers. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 2774–2784

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Section: Resultssupporting

confidence: 79%

Conjugated polymers with carbazole, fluorene, and ethylene dioxythiophene in the main chain and a pendant cyano group: Synthesis, photophysical, and electrochemical studies

Anand

Ramachandran

Dhamodharan

2016

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

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“…64,65 These PIs exhibited interesting fluorescent and resistive switching (ON-OFF) characteristics, low dielectric constants, exceptional thermal stabilities and excellent mechanical properties, mainly due to their rigid non- Triarylamine polymeric resistor-type memory devices H-J Yen and G-S Liou planar-conjugated structures. Memory devices with the ITO/P13/Al configuration exhibited the distinct volatile memory characteristics of SRAM.…”

Section: Sram Propertiesmentioning

confidence: 99%

Solution-processable triarylamine-based high-performance polymers for resistive switching memory devices

Yen

Liou

2015

Polym J

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This review summarizes the most widely used mechanisms in high-performance polymeric resistive memory devices, such as charge transfer, space charge trapping and filament conduction. In addition, recent studies of functional high-performance polymers for memory device applications are reviewed, compared and differentiated based on the mechanisms and structural design methods used. By carefully designing the polymeric structure based on these systematically investigated switching mechanisms, almost all types of current memory characteristics can be reproduced, and these memory properties show extremely high endurance during long-term operation, which makes polyimides very suitable materials for memory applications. INTRODUCTION High-performance polymersToday, life without polymers is unimaginable. Polymers have become the major synthetic materials of the 21st century. High-performance polymers (HPPs) are particularly desirable. The synthesis and development of HPPs over the past 30 years have drawn the attention of many polymer scientists and investigators. These polymers generally possess excellent physical deformation resistance and chemical deterioration resistance at high temperatures over long periods of time. The quest for HPPs began in the late 1950s to meet the demands of the military, aerospace, machine-building and electronics industries, among many other industrial applications.Hill and Walker 1 first noted that the incorporation of aromatic segments into a polymer generally results in a notable increase in its thermal stability. For this reason, much of the research work has been directed toward aromatic compositions. Hence, HPPs usually tend to contain large numbers of aromatic units in their structures. Several of these aromatic HPPs have been used for commercial applications, such as aromatic polyamides, polyimides, polyesters, polysulfones, polytriphenylamine and heterocyclic polymers (Scheme 1). Aromatic polyamides (aramids) and polyimides, such as DuPont's Kevlar fiber and Kapton film, respectively, have been well known for a long time and constantly attract more interest than other HPPs for their useful properties, such as excellent thermal and oxidative stabilities, high mechanical strengths, low flammabilities and good chemical and radiation resistances. [2][3][4][5][6][7][8][9][10][11][12][13] However, the rigidity of the backbone and strong hydrogen bonding of these HPPs result in high melting or glass-transition

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“…One approach involves decreasing the polarizability of polymers by methods such as incorporating fluorinated or alicyclic groups into polymer chains . The other method increases the free volume of polymers, that is, introducing high‐molar‐volume structures or air into PI matrix. The two approaches can be combined to achieve PI materials with considerably low dielectric constants.…”

Section: Introductionmentioning

confidence: 99%

High‐T_g porous polyimide films with low dielectric constant derived from spiro‐(adamantane‐2,9′(2′,7′‐diamino)‐fluorene)

Zhou

Dai

et al. 2018

J of Applied Polymer Sci

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Porous polyimide (PI) films with low dielectric constants and excellent thermal properties have been a pressing demand for the next generation of high‐performance, miniature, and ultrathin microelectronic devices. A series of novel porous PI films containing fluorenyl‐adamantane groups were prepared successfully via thermolysis of poly(ethylene glycol) (PEG) added in the PI matrix. The cross‐sectional morphologies of porous PI films showed closed pores with diameters ranging from 135 to 158 nm, which were uniform and regular in shape without interconnectivity. These porous PI films exhibited excellent thermal properties with a glass‐transition temperature at 376 °C whereas the 5% weight loss temperature in air excess of 405 °C due to enhanced rigidity afforded by fluorenyl‐adamantane groups. Accompanied by thermolysis content of PEG increasing from 0 to 20 wt %, the density of porous PI films decreased, and the corresponding porosity grew significantly from 0 to 11.48%. Depending on porosity, the dielectric constant and dielectric loss of porous PI films significantly declined from 2.89 to 2.37 and from 0.050 to 0.021, respectively. These excellent properties benefit the as‐prepared porous PI films for application as interlayer dielectrics, integrated circuit chips, or multichip modules in microelectronic fields. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47313.

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Synthesis and properties of high‐performance functional polyimides containing rigid nonplanar conjugated tetraphenylethylene moieties

Cited by 57 publications

References 56 publications

Conjugated polymers with carbazole, fluorene, and ethylene dioxythiophene in the main chain and a pendant cyano group: Synthesis, photophysical, and electrochemical studies

Conjugated polymers with carbazole, fluorene, and ethylene dioxythiophene in the main chain and a pendant cyano group: Synthesis, photophysical, and electrochemical studies

Solution-processable triarylamine-based high-performance polymers for resistive switching memory devices

High‐T_g porous polyimide films with low dielectric constant derived from spiro‐(adamantane‐2,9′(2′,7′‐diamino)‐fluorene)

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Synthesis and properties of high‐performance functional polyimides containing rigid nonplanar conjugated tetraphenylethylene moieties

Cited by 57 publications

References 56 publications

Conjugated polymers with carbazole, fluorene, and ethylene dioxythiophene in the main chain and a pendant cyano group: Synthesis, photophysical, and electrochemical studies

Conjugated polymers with carbazole, fluorene, and ethylene dioxythiophene in the main chain and a pendant cyano group: Synthesis, photophysical, and electrochemical studies

Solution-processable triarylamine-based high-performance polymers for resistive switching memory devices

High‐Tg porous polyimide films with low dielectric constant derived from spiro‐(adamantane‐2,9′(2′,7′‐diamino)‐fluorene)

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High‐T_g porous polyimide films with low dielectric constant derived from spiro‐(adamantane‐2,9′(2′,7′‐diamino)‐fluorene)