846-20-8

Usage

Uses

Used in Polyimide Films and Coatings Production:
2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride is used as a key component in the production of polyimide films and coatings due to its high thermal stability, excellent mechanical properties, and resistance to chemicals and solvents.
Used in Organic Compounds Synthesis:
2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride is used as a building block in the synthesis of various organic compounds, contributing to the development of new materials and products.
Used in Drug Development:
2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride is used as a starting material in drug development, owing to its potential applications in the creation of pharmaceutical compounds.
Used in Pharmaceutical Applications:
2-bromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride is used as a subject of research for its potential antibacterial and antifungal properties, indicating its possible use in the development of new pharmaceuticals for treating infections.

Upstream product

• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 

Downstream Products

• 926643-78-9 N,N′-bis(n-octyl)-2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic diimide 
• 942130-54-3 N,N’-bis(n-octyl)-2-bromonaphthalene-1,4,5,8-bis(dicarboximide) 
• 1315605-26-5 N,N'-di(n-hexyl)-2-bromonaphthalene-1,4,5,8-bis(dicarboximide) 
• 1224622-74-5 2-bromo-1,4,5,8-tetra(n-butoxycarbonyl)naphthalene 
• 1224622-75-6 2,6-dibromo-1,4,5,8-tetra(n-butoxycarbonyl)naphthalene 

Relevant academic research and scientific papers

Organic room-temperature phosphorescence from halogen-bonded organic frameworks: hidden electronic effects in rigidified chromophores

Development of purely organic materials displaying room-temperature phosphorescence (RTP) will expand the toolbox of inorganic phosphors for imaging, sensing or display applications. While molecular solids were found to suppress non-radiative energy dissipation and make the RTP process kinetically favourable, such an effect should be enhanced by the presence of multivalent directional non-covalent interactions. Here we report phosphorescence of a series of fast triplet-forming tetraethyl naphthalene-1,4,5,8-tetracarboxylates. Various numbers of bromo substituents were introduced to modulate intermolecular halogen-bonding interactions. Bright RTP with quantum yields up to 20% was observed when the molecule is surrounded by a Br?O halogen-bonded network. Spectroscopic and computational analyses revealed that judicious heavy-atom positioning suppresses non-radiative relaxation and enhances intersystem crossing at the same time. The latter effect was found to be facilitated by the orbital angular momentum change, in addition to the conventional heavy-atom effect. Our results suggest the potential of multivalent non-covalent interactions for excited-state conformation and electronic control. This journal is

Asymmetrically Substituted Quadruplex-Binding Naphthalene Diimide Showing Potent Activity in Pancreatic Cancer Models

Targeting of genomic quadruplexes is an approach to treating complex human cancers. We describe a series of tetra-substituted naphthalene diimide (ND) derivatives with a phenyl substituent directly attached to the ND core. The lead compound (SOP1812) has 10 times superior cellular and in vivo activity compared with previous ND compounds and nanomolar binding to human quadruplexes. The pharmacological properties of SOP1812 indicate good bioavailability, which is consistent with the in vivo activity in xenograft and genetic models for pancreatic cancer. Transcriptome analysis shows that it down-regulates several cancer gene pathways, including Wnt/β-catenin signaling.

Controlling intermolecular redox-doping of naphthalene diimides

Naphthalene diimide (NDI) with tertiary amine side chains is used to n-dope a series of NDI derivatives of varying energy levels. We demonstrate a photoinduced, intermolecular redox-doping process in which a dimethylpropyl amine side chain attached to one NDI reduces another NDI derivative to form radical anions. The influence of the aromatic core substituents on energy levels, doping efficacy and radical anion stability is studied by cyclic voltammetry, UV-Vis and electron paramagnetic resonance (EPR) spectroscopy. In general, the HOMO energy level of the NDI is responsible for the doping process and the LUMO for air stability of the resulting radical anion. The most electron deficient NDI derivative having two cyano substituents displays the highest doping yield and yields air stable radical anions for both light- and thermally-induced doping. Thermal doping is further accompanied by morphologic changes that stabilize radical anions in air.

Quinoidization of π-Expanded Aromatic Diimides: Photophysics, Aromaticity, and Stability of the Novel Quinoidal Acenes

We report the synthesis and photophysical characterization of π-expanded quinoidal triplet chromophores which exhibit attractive light-harvesting properties. The kinetic of the triplet excited state of quinoidal benzotetraphene 2 was found to be one order of magnitude higher than the lifetime of 3(1)* from the less conjugated parent chromophore 1. Furthermore, the evaluation of the optoelectronic properties indicates that π-expansion helps narrow the optoelectronic band gap, but the influence of the additional aromatic rings in the structure of 2 and 3 compromises the stability of the p-quinoidal ring. QDM 2 was isolated and fully characterized; however, it was found to rearomatize to a mixture of uncharacterized radical species.

Targeting Multiple Effector Pathways in Pancreatic Ductal Adenocarcinoma with a G-Quadruplex-Binding Small Molecule

Human pancreatic ductal adenocarcinoma (PDAC) involves the dysregulation of multiple signaling pathways. A novel approach to the treatment of PDAC is described, involving the targeting of cancer genes in PDAC pathways having over-representation of G-quadruplexes, using the trisubstituted naphthalene diimide quadruplex-binding compound 2,7-bis(3-morpholinopropyl)-4-((2-(pyrrolidin-1-yl)ethyl)amino)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone (CM03). This compound has been designed by computer modeling, is a potent inhibitor of cell growth in PDAC cell lines, and has anticancer activity in PDAC models, with a superior profile compared to gemcitabine, a commonly used therapy. Whole-transcriptome RNA-seq methodology has been used to analyze the effects of this quadruplex-binding small molecule on global gene expression. This has revealed the down-regulation of a large number of genes, rich in putative quadruplex elements and involved in essential pathways of PDAC survival, metastasis, and drug resistance. The changes produced by CM03 represent a global response to the complexity of human PDAC and may be applicable to other currently hard-to-treat cancers.

Core-substituted naphthalenediimides anchored on BiVO4 for visible light-driven water splitting

In this work, a novel catalytic system for the sunlight-driven water splitting reaction, which exploits the photocatalytic ability of BiVO4 coupled to a new kind of noble-metal-free organic dye molecules, is proposed. Hence, mono- and di-substituted naphthalenediimides (NDIs) were designed to have different functional groups that provide to them both tunable optical properties and adjustable HOMO/LUMO levels, and were selectively prepared (starting from 1,4,5,8-naphthalenetetracarboxylic acid) achieving yields >69%. Smart anchoring groups (i.e. carboxylates or aromatic amines) were added to the dyes in order to allow them to covalently bond to acidic -OH groups present on the BiVO4 surface. An easy and low-cost room temperature dip-coating technique was used to dye-sensitize both BiVO4 powders and thin films. NMR, MS, FT-IR, TG, FESEM, XRD, XPS and optical analyses confirmed the successful organic synthetic routes and good dyes/BiVO4 linkages. Photochemical and photoelectrochemical water oxidation reaction tests, together with DFT calculations, demonstrated that a proper alignment of the semiconductor/NDI-based dye energy levels is fundamental for enhancing the photocatalyst performance through a Z-scheme mechanism. The ability of the NDI organic molecules to delocalize the electronic charges was also a key factor for minimizing recombination processes and achieving more than a ten-fold increase in the photocurrent density of a 6 cm2 BiVO4 photo-electrode. The here reported results open new perspectives for the utilization of this new series of core-substituted NDIs, which are able to improve the activity of photocatalysts for different sunlight-driven applications, e.g. waste water treatment and organic contaminants' degradation, other than the production of solar fuels by water splitting mechanisms.

Rational synthesis of Ab-type n -substituted core-functionalized naphthalene diimides (cNDIs)

Acid-mediated transformation of tetraethyl 2,6-diethoxynaphthalene-1,4,5,8-tetracarboxylate selectively affords the core-substituted naphthalene-anhydride-ester (cNAE) in quantitative yield. This anhydride can be selectively converted into hetero-N-substituted core-functionalized naphthalene diimides (cNDIs) through sequential condensation reactions in the presence of the precursor amine with very high isolated yields over four steps. The approach can be applied to prepare a large variety of heterocyclic, aromatic, and aliphatic heterodiimides.

Synergetic effect of CN∧N/C∧N∧N coordination and the arylacetylide ligands on the photophysical properties of cyclometalated platinum complexes

Six coordinated Pt(II) complexes were prepared, in which the CN∧N or the C∧N∧N ligand were used to form the Pt(II) coordination center. For each coordination profile, three different arylacetylide ligands were used, i.e. naphthalenediimide (NDI), pyrenyl (Py) and naphthaleneimide (NI) acetylides. The electrochemical and the photophysical properties of the complexes were studied with steady-state and time-resolved absorption and emission spectroscopy, cyclic voltammetry and DFT calculations. The photostability and the photoluminescent properties of the complexes are finely tuned by the photoredox and photophysical properties of the arylacetylide ligands and the CN∧N/C∧N∧N Pt(II) coordination center. The triplet excited states of the complexes are an intraligand feature and the lifetime is long (90.1 μs). The photophysical properties of the complexes were rationalized with DFT calculations. The complexes were used as triplet photosensitizer for triplet-triplet annihilation upconversion. The upconversion quantum yield was up to 29.7%. The results are useful for future designing of Pt(II) complexes showing strong visible light-absorption, RT phosphorescence and long-lived triplet excited states.

REACTION PRODUCTS OF STANNYL DERIVATIVES OF NAPHTHALENE DIIMIDES WITH RYLENE COMPOUNDS

NDI-tin compounds are reacted with rylene compounds to form NDI-rylene compounds. The rylene compounds can be perylene compounds. The NDI-rylene compounds can be used in organic electronic devices including in a field-effect transistor.

Hybrid rylene arrays via combination of stille coupling and C-H transformation as high-performance electron transport materials

Hybrid rylene arrays have been prepared via a combination of Stille coupling and C-H transformation. The ability to extend the π system along the equatorial axis of rylenes not only leads to broadened light absorption but also increases the electron affinity, which can facilitate electron injection and transport with ambient stability.