187536-95-4

Upstream product

• 81-84-5 1,8-Naphthalic anhydride 
• 24544-04-5 2,6-diisopropylbenzenamine 
• 929103-36-6 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)naphthalene 
• 1246857-77-1 N-(2,6-diisopropylphenyl)-4,5-dibromonaphthalene-1,8-dicarboximide 
• 13577-26-9 6,7-dibromo-1H,3H-naphtho<1,8-cd>pyran-1,3-dione 
• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 
• 187536-93-2 6-bromo-2-(2,6-diisopropylphenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 165550-61-8 N-(2,6-diisopropylphenyl)perylene-3,4-dicarboximide 
• 187536-92-1 N-(2,6-diisopropylphenyl)-9-(4-N-(2,6-diisopropylphenyl)naphthalene-1,8-dicarboximide)perylene-3,4-dicarboximide 

Downstream Products

• 464885-23-2 N,N’-di(2,6-diisopropylphenyl)-1,6,9,13-tetrabromoterrylene-3,4:11,12-tetracarboxdiimide 

Relevant academic research and scientific papers

Electronic Modulation of Terrylene Diimides Leading to Core-Twisting, Tunable Emission and Intermolecular Interactions

Three new symmetrically para-phenylethynylene-substituted terrylene diimide derivatives namely, TDI-Ph, TDI-PhCN and TDI-PhNMe2 were synthesized to study the electronic effects on the structure and properties. The solid-state single-crystal structures for TDI-Ph and TDI-PhCN as well as for the precursor TDI-Br4 are presented. The X-ray diffraction studies revealed twisting in the bay-area of terrylene core, which improved the solubility as well, despite of having some of the shortest intermolecular Br···Br and C-H···O interactions in TDI-Br4. All the compounds exhibited near infra-red absorption and emission except for TDI-PhNMe2; especially TDI-PhNMe2 showed interesting broad absorption ranging from 300 to 970 nm. Further, the effects of electron-donating and accepting unit on electrochemical and optical properties have been investigated.

A General Synthetic Route to Polycyclic Aromatic Dicarboximides by Palladium-Catalyzed Annulation Reaction

Here we report a general method for the synthesis of polycyclic aromatic dicarboximides (PADIs) by palladium-catalyzed annulation of naphthalene dicarboximide to different types of aromatic substrates. Reaction conditions were optimized by systematic vari

Practical Syntheses of Terrylene Chromophores from Naphthalene and Perylene Building Blocks

A facile and efficient method to synthesize terrylene imides, a unique class of chromophores, and their derivatives from commercially available naphthalene and perylene building blocks is reported. We developed an extremely efficient Suzuki/C?H-arylation coupling cascade with Pd2(dba)3/PCy3 (dba=dibenzylidenacetone, Cy=cyclohexyl) as the catalyst and highly soluble naphthalene derivatives as starting materials. This efficiency allows purification via precipitation and crystallization, avoiding time-consuming column chromatography. For the first time, the highly soluble 3,4,11,12-terrylene tetraester was prepared in gram scale with yields up to 75% which thus becomes a versatile starting material for the synthesis of new terrylene derivatives. The presented method not only allows the synthesis of terrylene dyes and pigments, but also presents a route towards perylene and terrylene monoimides which is an advantageous simplification of previously reported synthetic procedures. (Figure presented.).

The synthesis and aggregation-induced near-infrared emission of terrylenediimide-tetraphenylethene dyads

We design and synthesize terrylenediimide-tetraphenylethene dyads, which exhibit featured aggregation-induced near-infrared fluorescence with a maximum emission wavelength of up to 800 nm.

New soluble near-infrared dyes based on terrylene diimides with four aromatic heterocycles

Terrylene diimides with four aromatic heterocycles (AHTDIs) were synthesized under Stille Cross-coupling conditions and fully characterized by NMR and mass spectrometry. The aggregation of the terrylene diimide (TDI) was suppressed by four heterocycles substituents on the bay region, and these AHTDIs exhibited good solubility in common organic solvents. The effects of the substituted groups on the optical and electrochemical properties were also investigated. The introduction of four aromatic heterocycles on the bay of TDI resulted in significant red-shifts of the absorption peak (100 nm), corresponding to a decrease in the band gap from 1.82 to 1.50 eV. Furthermore, with four rich electron aromatic heterocycles, the AHTDIs showed 280 mV negative-shifts of first oxidation potentials and a new oxidation wave, corresponding to an increase in the HOMO levels from?-5.60 to?-5.28 eV. Two soluble NIR dyes based on terrylene diimides were synthesized by the introduction of aromatic heterocycles substituents on the bay region. The effects of the substituted groups on the optical and electrochemical properties were further investigated. Copyright

METHOD FOR THE PRODUCTION OF TERYLENE-3,4:11,12-TETRACARBOXYDIIMIDES BY DIRECT SYNTHESIS

The invention relates to a method for the production of terylene-3,4:11,12-tetracarboxydiimides (I) in which the variables have the following meanings: R, R' independently = H, optionally substituted alkyl or cycloalkyl, aryl or heteroaryl, R1

Synthesis and modification of terrylenediimides as high-performance fluorescent dyes

Two new synthetic approaches to terrylenediimides, highly photostable fluorescent dyes, are described. For the first time terrylenediimide has been synthesised in a straightforward procedure that makes large quantities available. The second route includes an efficient cross-coupling reaction followed by a cyclodehy-drogenation. Monofunctionalisation of the imide structure allows terrylenediimides now to be coupled with a variety of compounds, for example, by Suzuki cross-coupling, which can lead to an array of terrylenediimides with new functional groups such as hydroxy, amino, or carboxy groups needed to link up with other molecules. The functionalisation in the bay region is used to tune the properties of terrylenediimides and extend the range of applications, for example, by introducing water solubility. These tetrasubstituted terrylenediimides offer, depending on the substituents used, exciting features such as good solubility in common organic solvents, water solubility, or NIR absorption.

Terrylenimides: New NIR fluorescent dyes

Terrylenimides 3 and 4 represent a new class of blue colorants, exhibiting absorption maxima at 650 to 700 nm and fluorescence emissions in the NIR region (673 to 750 nm). The terrylenimides were synthesized by means of various organometallic coupling rea