299962-88-2

Upstream product

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

Downstream Products

• 943148-75-2 N,N′-bis-(2′,6′-diisopropylphenyl)-2,3,6,7-tetrabromo-naphthalenetetracarboxylic acid diimide 
• 1219501-17-3 4,5,9,10-tetrabromo-2,7-bis(2-octyldodecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone 
• 1257635-56-5 N,N'-di(2-decyltetradecyl)-[2,3-d:6,7-d']-bi[2-(1,3-dithiacyclopenten-2-ylidene)-2-phenyl acetonitrile]-naphthalene-1,4,5,8-tetracarboxylic acid diimide 
• 1351161-79-9 4,5,9,10-tetrabromo-2,7-bis(3,4,5-tris(dodecyloxy)phenyl)methylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)tetraone 
• 1351161-68-6 2,2'-[2,8-bis(3,4,5-tris(dodecyloxy)phenyl)methyl-1,2,3,7,8,9-hexahydro-1,3,7,9-tetraoxo[1,3]benzodithiolo[4,5,6,7-lmn][1,3]dithiolo[4,5-f][3,8]phenanthroline-5,11-diylidine]bis(malononitrile) 
• 1351161-70-0 2,2'-[2,8-bis(4-(tert-butyl)phenyl)-1,2,3,7,8,9-hexahydro-1,3,7,9-tetraoxo[1,3]benzodithiolo[4,5,6,7-lmn][1,3]dithiolo[4,5-f][3,8]phenanthroline-5,11-diylidine]bis(malononitrile) 
• 1351161-75-5 2,2'-[2-(4-(tert-butyl)phenyl-8-(2-octyldodecyl))-1,2,3,7,8,9-hexahydro-1,3,7,9-tetraoxo[1,3]benzodithiolo[4,5,6,7-lmn][1,3]dithiolo[4,5-f][3,8]phenanthroline-5,11-diylidine]bis(malononitrile) 
• 1351161-69-7 2,2'-[2,8-bis(N-(2-aminoethyl)-3,4,5-tris(dodecyloxy)benzamide)-1,2,3,7,8,9-hexahydro-1,3,7,9-tetraoxo[1,3]benzodithiolo[4,5,6,7-lmn][1,3]dithiolo[4,5-f][3,8]phenanthroline-5,11-diylidine]bis(malononitrile) 
• 1259935-85-7 N,N-dimesityl-2,3,6,7-tetrabromo-naphthalene-1,4,5,8-tetracarboxylic acid bisimide 
• 954374-43-7 2,3,6,7-tetrabromonaphthalene-1,8,4,5-tetracarboxylic acid N,N-dioctyldiimide 
• 943148-76-3 2,3,6,7-tetrabromo-1,4,5,8-naphthalenetetracarboxylic acid diimide 
• 943148-73-0 N,N'-bis(phenylethyl)-2,6-dibromonaphthalene-1,8;4,5-tetracarboximide 
• 943148-74-1 N,N'-bis(phenylethyl)-2,7-dibromonaphthalene-1,8;4,5-tetracarboximide 

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

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.

Rapid and mild synthesis of functionalized naphthalenediimides

(Chemical Equation Presented) Core-substituted naphthalenediimides (NDIs) are not often used in functional materials despite excellent properties because the harsh conditions used for their synthesis are incompatible with structural diversity. Here, we report rapid access to blue, red, and yellow NDIs under mild conditions with tolerance toward the additional presence of pertinent functional groups.