49546-11-4Relevant articles and documents
Metallated azo-naphthalene diimide based redox-active porous organic polymer as an efficient water oxidation electrocatalyst
Bhat, Sajad Ahmad,Das, Chayanika,Maji, Tapas Kumar
, p. 19834 - 19842 (2018)
The importance of developing a stable, efficient and low-cost catalyst for the oxygen evolution reaction (OER) is at its pinnacle due to the reaction's poor reaction kinetics. Porous organic polymers (POPs) have recently emerged as a versatile platform fo
Conformationally rigid molecular and polymeric naphthalene-diimides containing C6H6N2constitutional isomers
Abbinante, Vincenzo Mirco,Barba, Luisa,Calabrese, Gabriele,García-Espejo, Gonzalo,Giannici, Francesco,Guagliardi, Antonietta,Marini, Diego,Masciocchi, Norberto,Milita, Silvia,Pipitone, Candida
, p. 10875 - 10888 (2021/09/02)
Organic thin films based on naphthalenediimides (NDIs) bearing alkyl substituents have shown interesting properties for application in OLEDs, thermoelectrics, solar cells, sensors and organic electronics. However, the polymorphic versatility attributed to the flexibility of alkyl chains remains a challenging issue, with detrimental implications on the performances. Aryl analogues containing C6H6N2 constitutional isomers are herein investigated as one of the possible way-out strategies. The synthesis of molecular and polymeric species is described, starting from naphthaleneteracarboxyldianhydride with isomeric aromatic amines and hydrazine. The materials are fully characterized by spectroscopy, thermal and structural X-ray diffraction methods, both as bulk powders and thin films, revealing a rich structural landscape. Depending on the stereochemistry of the branching aryls, the compounds show a variety of parallel stacking of the NDI cores, and high structural stability upon heating, up to 560 °C in the polymeric form. Thin films prepared by spin coating from organic solvent solutions and studied by grazing-incidence X-ray diffraction exhibit a high degree of crystallinity indicating the intrinsic tendency of these molecules to self-assemble in an ordered fashion without the need for any post-processing technique. In line with other NDI-based diimides, UV-vis spectroscopy indicates the optical band gaps falling in the visible region (2.87-3.02 eV). DFT calculations reveal a significant lowering of the frontier orbital energies of the hydrazido derivative. Beyond solution processing, the high thermal stability and the absence of polymorphic forms of these materials suggest that sublimation-based routes for films and device preparation can also be followed. This journal is
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.,Dos S. Abreu, Dieric,Timm, Ronaldo A.,Diógenes, Izaura C. N.,Kubota, Lauro T.,Abru?a, Héctor D.,Dichtel, William R.
supporting information, p. 13225 - 13229 (2015/11/09)
Porous polymer networks (PPNs) are attractive materials for capacitive energy storage because they offer high surface areas for increased double-layer capacitance, open structures for rapid ion transport, and redox-active moieties that enable faradaic (pseudocapacitive) energy storage. Here we demonstrate a new attractive feature of PPNs - the ability of their reduced forms (radical anions and dianions) to interact with small radii cations through synergistic interactions arising from densely packed redox-active groups, only when prepared as thin films. When naphthalene diimides (NDIs) are incorporated into PPN films, the carbonyl groups of adjacent, electrochemically generated, NDI radical anions and dianions bind strongly to K+, Li+, and Mg2+, shifting the formal potentials of NDI's second reduction by 120 and 460 mV for K+ and Li+-based electrolytes, respectively. In the case of Mg2+, NDI's two redox waves coalesce into a single two-electron process with shifts of 240 and 710 mV, for the first and second reductions, respectively, increasing the energy density by over 20 % without changing the polymer backbone. In contrast, the formal reduction potentials of NDI derivatives in solution are identical for each electrolyte, and this effect has not been reported for NDI previously. This study illustrates the profound influence of the solid-state structure of a polymer on its electrochemical response, which does not simply reflect the solution-phase redox behavior of its monomers.
