Comparative study of the synthetic methods for perylene-based covalent triazine polyimides

Kim, Hong Mo; Jang, Ho Kyung; Hwang, Tae Gyu; Namgoong, Jin Woong; Kim, Jeong Yun; Yuk, Sim Bum; Kim, Jae Pil

doi:10.1016/j.dyepig.2020.108968

Cited by 13 publications

(10 citation statements)

References 29 publications

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“…t-PTPI and i-PTPI have been fabricated using the trimerization reaction with an acid catalyst and the polycondensation reactions, respectively. 104 The results demonstrate that these diverse synthesis methods cause considerable differences in thermal stability, chemical structure, porosity, and crystallinity. Both PTPIs exhibit excellent thermal stability.…”

Section: Other Approachesmentioning

confidence: 96%

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Design, synthesis, and application of covalent organic frameworks as catalysts

Nikkhoo¹,

Mallakpour

Hussain

2023

New J. Chem.

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Section: Other Approachesmentioning

confidence: 96%

“…For fabricating crystalline and stable perylene-based CTFs, the polyimidization approach is more efficient. 104 Owing to its low density and intrinsic porosity, hierarchical porous COF foam has exceptional importance. To fabricate this COF (Fig.…”

Section: Other Approachesmentioning

confidence: 99%

Design, synthesis, and application of covalent organic frameworks as catalysts

Nikkhoo¹,

Mallakpour

Hussain

2023

New J. Chem.

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“…Covalent triazine frameworks (CTF) is an important class of COFs, which is usually constructed by self‐polymerization of −CN via Reaction G [38] . Polyimide COFs were synthesized through a solvothermal route using polyimidization reaction of 1,3,5‐tris‐(4‐aminophenyl)triazine (TAPT) and perylene‐3,4,9,10‐tetracarboxylic dianhydride (PDA) by Reaction H [39] . The first example of olefin‐linked 2D conjugated crystalline COFs was reported by Zhuang and co‐workers via Knoevenagel polycondensation reaction (Reaction I) of 1,4‐phenylene diacetonitrile and 1,3,5‐tri(4‐formylphenyl)benzene [40] .…”

Section: Design and Preparation Of Cofsmentioning

confidence: 99%

“…[36] Zhang and co-workers synthesized an imine COF by Schiff base reaction of 2,4,6-trihydroxybenzene-1,3,5tricarbaldehyde (Tp) and o-tolidine (Reaction F). [37] Covalent triazine frameworks (CTF) is an important class of COFs, which is usually constructed by self-polymerization of À CN via Reaction G. [38] Polyimide COFs were synthesized through a solvothermal route using polyimidization reaction of 1,3,5-tris-(4-aminophenyl)triazine (TAPT) and perylene-3,4,9,10-tetracarboxylic dianhydride (PDA) by Reaction H. [39] The first example of olefin-linked 2D conjugated crystalline COFs was reported by Zhuang and co-workers via Knoevenagel polycondensation reaction (Reaction I) of 1,4-phenylene diacetonitrile and 1,3,5tri(4-formylphenyl)benzene. [40] Perepichka's group constructed a series of conjugated COFs for fluorescent probes through Michael addition-elimination reaction, as presented in Reaction J.…”

Section: Design and Preparation Of Cofsmentioning

confidence: 99%

Covalent Organic Frameworks (COFs): A Necessary Choice For Drug Delivery

et al. 2022

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Some drug molecules with strong chemical activity are unstable in the biological environment and difficult to reach the target, so no matter how good the drug is, it cannot completely prove its efficacy. And drugs need good vectors to help them deliver to their target, where they work best. In recent years, covalent organic frameworks (COFs) have been developed for drug delivery applications due to their regular pore structure, good biocompatibility, topological controllability, and modifiability. In the process of drug delivery, COFs have many advantages such as high drug adsorption capacity, good stability in the biological environment, strong targeting of lesions, and weak cytotoxicity. At present, a lot of work using COFs as drug molecular carriers has been reported, and this minireview summarizes the mechanism of COFs drug delivery and related applications in recent years (drug adsorption and release), by which we expect to achieve more ideas for the future design of drug delivery related COFs and push forward the development of COFs in drug delivery.

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“…It is thus necessary to increase the electron-withdrawing property of the dianhydride or the electron-donating property of the diamine, placing demands on the molecular design of monomers. Though introduced structures such as perylene and triazine lower the gap energy of PI to 1.94 eV or even 0.93–0.91 eV, , this is at the expense of low monomer activity, poor monomer solubility, severe performance loss, and great changes in the original process, making the homopolymerization method uneconomical. Therefore, there is an urgent need to devise a new method for the preparation of intrinsically BPI.…”

Section: Introductionmentioning

confidence: 99%

Intrinsically Black Polyimide with Retained Insulation and Thermal Properties: A Black Anthraquinone Derivative Capable of Linear Copolymerization

et al. 2021

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Black polyimide (BPI) is increasingly in demand for the development of photoelectric devices in place of yellow transparent polyimide, but BPI doped with carbon black shows serious insulation and mechanical performance deficiencies due to pinholes and uneven dispersion. Intrinsically BPI has thus attracted increasing interest in science and industry. Anthraquinone derivatives have an ample high molar extinction coefficient (ε), and appending as many auxochromes (−OH and −NH2) as possible on the anthraquinone skeleton can extend its light absorption range, thereby achieving complete UV–visible light absorption. However, the greatest obstacle to its application in BPI is retaining the monomer bifunctionality to avoid gel formation. In this work, a linearly polymerizable anthraquinone derivative, 2,4,5,7-tetraamino-1,8-dihydroxyanthracene-9,10-dione (4NADA), has been developed. Structural analysis of this monomer bearing multiple active groups by 1H NMR, Fourier-transform infrared, and theoretical calculations has demonstrated that the auxochrome groups show different nucleophilic activities owing to the formation of intramolecular hydrogen bonds, such that only p-amino groups (2- and 7-positions) can participate in the polymerization reaction. Subsequently, 4NADA was copolymerized into a Kapton-type polyimide. We found that low-level introduction of 4NADA (4%) afforded a spectrally BPI film that maintained the electrical insulation and heat resistance properties of polyimide. This method, equivalent to embedding a black monomer in polyimide chains, has merits of economy, universality, process consistency, ready accessibility, and superior performance.

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Comparative study of the synthetic methods for perylene-based covalent triazine polyimides

Cited by 13 publications

References 29 publications

Design, synthesis, and application of covalent organic frameworks as catalysts

Design, synthesis, and application of covalent organic frameworks as catalysts

Covalent Organic Frameworks (COFs): A Necessary Choice For Drug Delivery

Intrinsically Black Polyimide with Retained Insulation and Thermal Properties: A Black Anthraquinone Derivative Capable of Linear Copolymerization

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