24259-89-0Relevant academic research and scientific papers
Energy-saving and long-life electrochromic materials of naphthalene diimide-cored pyridinium salts
Gong, Cheng-Bin,Huang, Zhen-Jie,Li, Feng,Pan, Ming-Yue,Tang, Qian,Zhou, Qian-Hua
, p. 10031 - 10038 (2020)
Developing electrochromic materials with energy-saving (i.e., low driving voltage) and long-life (i.e., high switching stability) properties is highly desirable with respect to practical application. In this work, we report the synthesis of two N,N′-di(4-pyridyl)-1,4,5,8-naphthalene diimide derivatives (DPNDIs), (Me2DPNDI)·(2I) and (benzyl2DPNDI)·(2Br), and the characterization of their electrochemical and electrochromic properties. Both DPNDIs showed two quasi-reversible redox couples in the cyclic voltammograms with cathodic peak potentials of approximately-0.30 and-0.70 V vs. Ag/Ag+. The electrochromic devices based on ((Me2DPNDI)·(2I) and (benzyl2DPNDI)·(2Br)) gave a colored state of dark orange and orange, respectively, which are colored states that have rarely been reported, and both DPNDIs had a low onset bias of-0.7 V and good switching stabilities (the change in optical contrast after 7200 s of 4%). The introduction of pyridinium salts at the DPNDI core enhanced its solubility and switching stability. In combination with density functional theory (DFT) calculations, it was shown that the formation of pyridinium salts modified the electronic properties of 1,4,5,8-naphthalenetetracarboxylic dianhydride (NDA) and DPNDI, and both pyridinium salt and NDA units contributed to electrochemical reduction. The results demonstrate that (Me2DPNDI)·(2I) and (benzyl2DPNDI)·(2Br) are promising electrochromic materials and can be used in energy-saving buildings, smart windows, traffic signs, electronic paper, sunglasses, and anti-glare rearview mirrors.
Carbonyl conjugated heterocyclic compound and preparation and application
-
Paragraph 0020; 0027-0034; 0043-0050; 0053-0060, (2017/08/28)
The invention belongs to the field of lithium ion battery materials, and discloses a carbonyl conjugated heterocyclic compound and preparation and application. The carbonyl conjugated heterocyclic compound is N,N'-diphenyl-1,4,5,8-naphthalimide, and has a structural formula shown as a formula (I). A preparation method comprises the following steps: dissolving 1,4,5,8-naphthalenetetracarboxylic dianhydride in a solvent, stirring to mix uniformly, dropwise adding phenylamine and trithylamine, stirring and performing a refluxing reaction until brown precipitate is generated; separating and washing the precipitate, recrystallizing, washing and drying in vacuum to obtain a product. In the preparation method, a product is prepared through a one-pot reaction, and a synthetic method is simple and feasible, is low in cost, has high yield, saves energy and is environment-friendly. The prepared N,N'-diphenyl-1,4,5,8-naphthalimide has high discharging capacity, high cycling stability and high rate performance after thermal treatment, and is a promising positive electrode material for a lithium ion battery. The formula (I) is shown in the description.
Green and highly efficient synthesis of perylene and naphthalene bisimides in nothing but water
Baumgartner, Bettina,Svirkova, Anastasiya,Bintinger, Johannes,Hametner, Christian,Marchetti-Deschmann, Martina,Unterlass, Miriam M.
supporting information, p. 1229 - 1232 (2017/02/05)
High-purity, symmetrically substituted perylene and naphthalene bisimides were obtained by hydrothermal condensation of monoamines with the corresponding bisanhydride. The hydrothermal imidization proceeds quantitatively, without the need for organic solvents, catalysts or excess of the amines.
Boundaries of anion/naphthalenediimide interactions: From anion-π interactions to anion-induced charge-transfer and electron-transfer phenomena
Guha, Samit,Goodson, Flynt S.,Corson, Lucas J.,Saha, Sourav
supporting information; experimental part, p. 13679 - 13691 (2012/10/08)
The recent emergence of anion-π interactions has added a new dimension to supramolecular chemistry of anions. Yet, after a decade since its inception, actual mechanisms of anion-π interactions remain highly debated. To elicit a complete and accurate understanding of how different anions interact with π-electron-deficient 1,4,5,8-naphthalenediimides (NDIs) under different conditions, we have extensively studied these interactions using powerful experimental techniques. Herein, we demonstrate that, depending on the electron-donating abilities (Lewis basicity) of anions and electron-accepting abilities (π-acidity) of NDIs, modes of anion-NDI interactions vary from extremely weak non-chromogenic anion-π interactions to chromogenic anion-induced charge-transfer (CT) and electron-transfer (ET) phenomena. In aprotic solvents, electron-donating abilities of anions generally follow their Lewis basicity order, whereas π-acidity of NDIs can be fine-tuned by installing different electron-rich and electron-deficient substituents. While strongly Lewis basic anions (OH- and F-) undergo thermal ET with most NDIs, generating NDI?- radical anions and NDI 2- dianions in aprotic solvents, weaker Lewis bases (AcO-, H2PO4-, Cl-, etc.) often require the photoexcitation of moderately π-acidic NDIs to generate the corresponding NDI?- radical anions via photoinduced ET (PET). Poorly Lewis basic I- does not participate in thermal ET or PET with most NDIs (except with strongly π-acidic core-substituted dicyano-NDI) but forms anion/NDI CT or anion-π complexes. We have looked for experimental evidence that could indicate alternative mechanisms, such as a Meisenheimer complex or CH anion hydrogen-bond formation, but none was found to support these possibilities.
Electronically regulated thermally and light-gated electron transfer from anions to naphthalenediimides
Guha, Samit,Goodson, Flynt S.,Roy, Sovan,Corson, Lucas J.,Gravenmier, Curtis A.,Saha, Sourav
supporting information; experimental part, p. 15256 - 15259 (2011/11/05)
Anion-induced electron transfer (ET) to π-electron-deficient naphthalenediimides (NDIs) can be channeled through two distinct pathways by adjusting the Lewis basicity of the anion and the π-acidity of the NDI: (1) When the anion and NDI are a strong elect
1,4;5,8-naphthalene-tetracarboxylic diimide derivatives as model compounds for molecular layer epitaxy
Ofir, Yuval,Zelichenok, Alexander,Yitzchaik, Shlomo
, p. 2142 - 2149 (2007/10/03)
The physical properties and finite size effects observed in 1,4;5,8-naphthalene-tetracarboxylicdiimide (NTCDI)-based organic multilayers assembled by molecular layer epitaxy (MLE) are investigated by structure-property studies of low molecular weight mode
Analgesic activity of cyclic imides: 1,8-Naphthalimide and 1,4,5,8- naphthalenediimide derivatives
Andricopulo, Adriano Defini,Mueller, Luciane A.,Cechinel Filho, Valdir,Cani, Graziela S.,Roos, Juliana F.,Correa, Rogerio,Santos, Adair Roberto S.,Nunes, Ricardo Jose,Yunes, Rosendo Augusto
, p. 319 - 321 (2007/10/03)
In early studies, we have reported the synthesis and biological activities of several cyclic imides. The present study describes the analgesic activity of 1,8-naphthalimide and 1,4,5,8-naphthalenediimide derivatives in a standard murine model of analgesia. The pharmacological results show that all compounds studied, given intraperitoneally, produced significant inhibition of acetic acid-induced abdominal constrictions. At the ID50 (μmol/kg) level, these cyclic imide derivatives were about 40-270- fold more potent in this assay than aspirin and acetaminophen, two well-known and widely used analgesics. These results extend previous studies on the analgesic activity of cyclic imides. (C) 2000 Elsevier Science S.A.
