Cation‐Dependent Stabilization of Electrogenerated Naphthalene Diimide Dianions in Porous Polymer Thin Films and Their Application to Electrical Energy Storage

DeBlase, Catherine R.; Hernández‐Burgos, Kenneth; Rotter, Julian M.; Fortman, David J.; Abreu, Dieric S.; Timm, Ronaldo Adriano; Diógenes, Izaura C.N.; Kubota, Lauro T.; Abruña, Héctor D.; Dichtel, William R.

doi:10.1002/anie.201505289

Cited by 92 publications

(93 citation statements)

References 39 publications

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“…In addition to COFs, other porous polymers also perform well in supercapacitors. For example, naphthalene diimide (NDI)‐containing porous polymer networks exhibit enhanced cell voltage and energy density, because of the counter cation‐dependent stabilization of electrogenerated NDI dianions in their thin films (Figure c) . Conjugated microporous polyaminoanthraquinone networks synthesized by Buchwald–Hartwig coupling between 2,6‐diaminoanthraquinone and aryl bromides were reported to demonstrate highly efficient supercapacitance properties .…”

Section: Electrochemical Energy Storagementioning

confidence: 99%

Porous Polymers as Multifunctional Material Platforms toward Task‐Specific Applications

et al. 2018

Advanced Materials

379

245

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have triggered serious threats to the survival and development of mankind. Consequently, exploring novel materials with task-specific applications is of fundamental importance for the sustainable development of economy and society. The burgeoning progress of nanomaterials in recent years has demonstrated that porosity is one of the essential factors in determining material properties for possible breakthroughs in their applications. Therefore, porous materials are playing important roles in many well-established applications and emerging technologies for challenging social and economic issues due to their intrinsic characteristics of large surface areas, open channels, and the possible control over the pore environment. According to International Union of Pure and Applied Chemistry, the pores of porous materials are classified into three categories by their pore sizes: micropores are smaller than 2 nm, mesopores are in the range of 2-50 nm, and macropores are larger than 50 nm. [1] Their pore walls include the organic skeleton (e.g., porous polymers, organic porous cages, and supramolecular organic frameworks), the inorganic skeleton (e.g., zeolites, porous carbons, and mesoporous silica), and the hybrid skeleton (e.g., metal-organic frameworks (MOFs)).Among the developed porous materials, porous polymers have attracted an increasing level of research interest owing to their potential to integrate the advantages of both porous materials and polymers. [2,3] Table 1 lists the characteristic structural features and properties of porous polymers, and gives a systematic comparison to other typical porous materials, such as zeolites, porous carbons, and MOFs. Porous polymers, zeolites, porous carbons, and MOFs share a number of features such as high permanent porosities, large surface areas, and designable pores and voids. However, they are different in several important aspects. The major advantages of porous polymers over many other porous materials are their chemical diversity and easy processability. Compared to zeolites and porous carbons, the synthesis of porous polymers is generally more versatile and can be approached in a way that conforms to the concept of rational materials design. Similar to MOFs, porous polymers inherit the excellent chemical and physical tunability afforded by the versatility of organic chemistry. Furthermore, Exploring advanced porous materials is of critical importance in the development of science and technology. Porous polymers, being famous for their all-organic components, tailored pore structures, and adjustable chemical components, have attracted an increasing level of research interest in a large number of applications, including gas adsorption/storage, separation, catalysis, environmental remediation, energy, optoelectronics, and health. Recent years have witnessed tremendous research breakthroughs in these fields thanks to the unique pore structures and versatile skeletons of porous polymers. Here, recent milestones in the diverse applications of porous polymers are presented, ...

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Section: Electrochemical Energy Storagementioning

confidence: 99%

Porous Polymers as Multifunctional Material Platforms toward Task‐Specific Applications

et al. 2018

Advanced Materials

379

245

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“…[140] The use of NDI buildingb locks for the construction of COFs has been focused on organic electrodes for energy storagea pplications,t aking advantage of the electrochemical properties (Scheme 6). [142][143][144] Dichtele tal. reported ar obust and insoluble porousN DI-containing b-ketoamine-linked COF (NDI-TFP,h igh- est BET value of 970 m 2 g À1 ), which was deposited as at hin film on gold electrodes.…”

Section: Naphtalene Diimide (Ndi)mentioning

confidence: 99%

Electroactive Organic Building Blocks for the Chemical Design of Functional Porous Frameworks (MOFs and COFs) in Electronics

Souto

Strutyński

Melle‐Franco

et al. 2020

Chemistry A European J

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Electroactive organic molecules have received a lot of attention in the field of electronics because of their fascinating electronic properties, easy functionalization and potential low cost towards their implementation in electronic devices. In recent years, electroactive organic molecules have also emerged as promising building blocks for the design and construction of crystalline porous frameworks such as metal–organic frameworks (MOFs) and covalent‐organic frameworks (COFs) for applications in electronics. Such porous materials present certain additional advantages such as, for example, an immense structural and functional versatility, combination of porosity with multiple electronic properties and the possibility of tuning their physical properties by post‐synthetic modifications. In this Review, we summarize the main electroactive organic building blocks used in the past few years for the design and construction of functional porous materials (MOFs and COFs) for electronics with special emphasis on their electronic structure and function relationships. The different building blocks have been classified based on the electronic nature and main function of the resulting porous frameworks. The design and synthesis of novel electroactive organic molecules is encouraged towards the construction of functional porous frameworks exhibiting new functions and applications in electronics.

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“…Indeed, both the redox potential [183][184][185][186][187][188][189][190] and structural properties [191][192][193] of organic compounds can be predicted by computational studies. However, innumerable organic molecules make it a daunting task to identify optimal structures by experimentation.…”

Section: Prospect Of Carbonyl Electrodes For Stationary Batteriesmentioning

confidence: 99%

Molecular Engineering with Organic Carbonyl Electrode Materials for Advanced Stationary and Redox Flow Rechargeable Batteries

2017

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Organic carbonyl electrode materials that have the advantages of high capacity, low cost and being environmentally friendly, are regarded as powerful candidates for next-generation stationary and redox flow rechargeable batteries (RFBs). However, low carbonyl utilization, poor electronic conductivity and undesired dissolution in electrolyte are urgent issues to be solved. Here, we summarize a molecular engineering approach for tuning the capacity, working potential, concentration of active species, kinetics, and stability of stationary and redox flow batteries, which well resolves the problems of organic carbonyl electrode materials. As an example, in stationary batteries, 9,10-anthraquinone (AQ) with two carbonyls delivers a capacity of 257 mAh g (2.27 V vs Li /Li), while increasing the number of carbonyls to four with the formation of 5,7,12,14-pentacenetetrone results in a higher capacity of 317 mAh g (2.60 V vs Li /Li). In RFBs, AQ, which is less soluble in aqueous electrolyte, reaches 1 M by grafting -SO H with the formation of 9,10-anthraquinone-2,7-disulphonic acid, resulting in a power density exceeding 0.6 W cm with long cycling life. Therefore, through regulating substituent groups, conjugated structures, Coulomb interactions, and the molecular weight, the electrochemical performance of carbonyl electrode materials can be rationally optimized. This review offers fundamental principles and insight into designing advanced carbonyl materials for the electrodes of next-generation rechargeable batteries.

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Cation‐Dependent Stabilization of Electrogenerated Naphthalene Diimide Dianions in Porous Polymer Thin Films and Their Application to Electrical Energy Storage

Cited by 92 publications

References 39 publications

Porous Polymers as Multifunctional Material Platforms toward Task‐Specific Applications

Porous Polymers as Multifunctional Material Platforms toward Task‐Specific Applications

Electroactive Organic Building Blocks for the Chemical Design of Functional Porous Frameworks (MOFs and COFs) in Electronics

Molecular Engineering with Organic Carbonyl Electrode Materials for Advanced Stationary and Redox Flow Rechargeable Batteries

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