106897-63-6

Basic information

• Product Name: Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone,2,7-bis(phenylmethyl)-
• Synonyms: N,N'-Bis(phenylmethyl)naphthalene-1,4,5,8-tetracarboxylicdiimide
• CAS NO: 106897-63-6
• Molecular Formula: C₂₈H₁₈N₂O₄
• Molecular Weight: 446.46
• Mol File: 106897-63-6.mol

Chemical Properties

• CAS DataBase Reference: Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone,2,7-bis(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone,2,7-bis(phenylmethyl)-(106897-63-6)
• EPA Substance Registry System: Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone,2,7-bis(phenylmethyl)-(106897-63-6)

Safety Data

• Hazard Codes: A poison.:
• Safety Statements: x." target="_blank">A poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.:
• Hazardous Substances Data: 106897-63-6(Hazardous Substances Data)

Upstream product

• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 
• 100-46-9 benzylamine 

Relevant articles and documents

Selective interaction of N,N-bis(aminobenzyl)naphthalenediimides with fluoride anion

In this work, the optical properties of N,N-bis(aminobenzyl)naphthalenediimides 2a–2d (BzNDIs) and their interaction with fluoride were studied. The results demonstrated that the amino group position in the benzyl substituent exerts an effect in the absorption and emission properties. Particularly, the N,N-bis(2-aminobenzyl)NDI 2b presented non-typical absorption and emission bands which indicate an intramolecular charge transfer from the amino phenyl group to the NDI core. As the concentration of 2b increases, the solution turns from colourless to a pale orange colour. The interaction of BzNDIs 2a–2d with anions was selective towards fluoride and the affinity was in the order para?>?ortho?>?meta with respect to the position of the amino group in the aminophenyl ring. Interestingly, the colour change in the solution of 2b upon addition of fluoride makes it a good candidate for a fluoride colorimetric detection. The voltammetry analysis indicates the ability of these molecules to accept two electrons, in consequence the interaction of two fluoride anions with the BzNDIs was observed.

Direct core functionalisation of naphthalenediimides by iridium catalysed C-H borylation

We report the first boron-substituted naphthalenediimides (NDIs), prepared by iridium catalysed C-H activation. When the NDI substrates bear N-benzyl substituents, the naphthyl NDI core is borylated in preference, suggestive of a directed borylation mechanism. Borylated NDIs are substrates for Suzuki-Miyaura couplings and borylation of an NDI bearing two inequivalent N-substituents has also been demonstrated. This journal is

Analgesic activity of cyclic imides: 1,8-Naphthalimide and 1,4,5,8- naphthalenediimide derivatives

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.

Photoinduced electron transfer in N,N-bis(pyridylmethyl)naphthalenediimides: study of their potential as pH chemosensors

The change in fluorescent properties of a series of N,N-bis(pyridylmethyl)naphthalenediimides (BIPy-NDIs) as function of pH were investigated. The naphthalenediimide dyes displayed OFF–ON pH sensing properties owing to photoinduced electron transfer in the pH range from 1.7 to 4.1. The fluorescence enhancement of the chemosensors studied is based on the hindering of photoinduced energy-electron transfer (PET) from pyridine ring to the naphthalene fluorophore by protonation. Moreover, using density functional theory theoretical calculations of molecular orbitals, it was verified that protonation nitrogen atom in pyridine ring inhibits the PET process. The best selective response for monitoring pH in the presence of different metal ions, was exhibited by BIPy-NDI 1B. In addition, 1B was applied for determination of pH in real samples of commercial vinegars. The results were consistent with those obtained by glass electrode method, indicating that the new probe could be a practical pH indicator in strongly acidic conditions.

Organic small molecule electron transport material based on naphthalimide unit and application thereof

The invention provides an organic small molecule electron transport material based on a naphthalimide unit and application thereof, belongs to the field of organic photoelectric materials, and solves the problems that in the prior art, the quantum dot light-emitting diode device is few in electron transport material selection and poor in device stability. The chemical structure of the organic small molecule electron transport material contains a naphthalimide unit, and the organic small molecule electron transport material has the advantages that 1) the lowest unoccupied molecular orbital energy level is low, electron injection and transport in a QLED device are facilitated, the highest occupied molecular orbital energy level is low, hole injection in the QLED device can be blocked, and the above two aspects are beneficial for improving the electroluminescent efficiency of the QLED device; (2) the absorption spectrum is mainly not located in a visible light region and does not absorb light emitted by the light-emitting layer in the QLED device; and 3) the material has a rigid configuration, can inhibit crystallization of the material, is beneficial to processing in a QLED, and is beneficial to improving the stability of a QLED device.

Encapsulation of Aromatic Guests in the Bisporphyrin Cavity of a Double-Stranded Spiroborate Helicate: Thermodynamic and Kinetic Studies and the Encapsulation Mechanism

A double-stranded spiroborate helicate bearing a bisporphyrin unit in the middle forms an inclusion complex with electron-deficient aromatic guests that are sandwiched between the porphyrins. In the present study, we systematically investigated the effects of size, electron density, and substituents of a series of aromatic guests on inclusion complex formations within the bisporphyrin. The thermodynamic and kinetic behaviors during the guest-encapsulation process were also investigated in detail. The guest-encapsulation abilities in the helicate increased with the increasing core sizes of the electron-deficient aromatic guests and decreased with the increasing bulkiness and number of substituents of the guests. Among the naphthalenediimide derivatives, those with bulky N-substituents at both ends hardly formed an inclusion complex. Instead, they formed a [2]rotaxane-like inclusion complex through the water-mediated dynamic B-O bond cleavage/reformation of the spiroborate groups of the helicate, which enhanced the conformational flexibility of the helicate to enlarge the bisporphyrin cavity and form an inclusion complex. Based on the X-ray crystal structure of a unique pacman-like 1:1 inclusion complex between the helicate and an ammonium cation as well as the molecular dynamics simulation results, a plausible mechanism for the inclusion of a planar aromatic guest within the helicate is also proposed.