85514-20-1

Usage

Uses

Used in Electronics Industry:
Perylene, 3,10-dibromois used as a fluorescent dye for the manufacturing of organic light-emitting diodes (OLEDs), solar cells, and other electronic devices. Its rigid and planar structure, along with the presence of bromine atoms, contributes to its high fluorescence efficiency and stability, making it an ideal candidate for these applications.
Used in Biological Research:
Perylene, 3,10-dibromois utilized as a molecular probe in biological research. Its fluorescent properties allow researchers to track and visualize specific biomolecules or cellular structures, providing valuable insights into biological processes and mechanisms.
Used in Chemical Synthesis:
Perylene, 3,10-dibromoserves as a chemical intermediate in the synthesis of other compounds. Its unique structure and reactivity make it a useful building block for the development of new materials and pharmaceuticals.
However, it is important to note that due to its high persistence and potential environmental and health risks, the usage and emissions of Perylene, 3,10-dibromoare regulated in many countries. This is to minimize its impact on ecosystems and human health, ensuring the sustainable development and application of Perylene, 3,10-dibromo-.

Upstream product

• 198-55-0 PERYLENE 
• 7726-95-6 bromine 
• 71-43-2 benzene 

Downstream Products

• 5796-93-0 perylene-3,10-dione 
• 116-71-2 isoviolanthrone 

Relevant academic research and scientific papers

MOLECULES AND OLIGOMERS FOR ENDOTHERMIC SINGLET FISSION

The present disclosure relates to a composition that includes a repeat unit defined by where each of R1, R2, R3, R4, R5, R6, R7, and R8 includes at least one of a hydrogen atom, a fluorine atom, and/or a first hydrocarbon chain having between 1 and 20 carbon atoms, inclusively, where each of A1, A2, A3 and A4 are either a carbon atom or a nitrogen atom, when A1 is a nitrogen atom, A2 is a carbon atom, when A2 is a nitrogen atom, A1 is a carbon atom, when A3 is a nitrogen atom, A4 is a carbon atom, when A4 is a nitrogen atom, A3 is a carbon atom, either A1 or A2 form a covalent bond, x, with a carbon atom, a, either A3 or A4 form a covalent bond, y, with a carbon atom, b, L is a linker group that includes an aromatic ring, and n is between 1 and 20, inclusively.

Synthesis of Perylene-Tagged Internal and External Electron Donors for Magnesium Dichloride Supported Ziegler-Natta Catalysts

We report on the synthesis of three perylene-tagged electron donors representing three major types- phthalates, diethers, and alkoxysilanes - which are of importance for the subsequent studies of MgCl 2 -supported Ziegler-Natta catalysts by means of laser scanning confocal fluorescence microscopy. The obtained products were unambiguously characterized, including by X-ray crystal structure analysis; their photophysical properties (absorption and emission spectra) were investigated as well. Additionally, a reliable and convenient protocol for the multigram synthesis of the required starting material - 3-bromoperylene (PerBr) - was developed. The key step of this method was synthesis of trialkylsilyl-substituted perylenes, which were further separated by means of flash chromatography followed by conversion of the isolated 3-trialkylsilyl-substituted product to PerBr.

Reliable and reproducible separation of 3,9-and 3,10-dibromoperylenes and the photophysical properties of their alkynyl derivatives

We developed a reliable and reproducible method for the separation of 3,9-dibromoperylene and 3,10-dibromoperylene resulting from bromination of perylene by using sequential and repeated recrystallization. Because of the unprecedented purities of the dibromoperylenes, they exhibit the high-est melting temperatures so far reported. In addition, various alkynylperylenes were prepared from the dibromoperylenes, and we investigated the photophysical characteristics of these alkynyl derivatives in detail.

CYANATED PERYLENE COMPOUNDS

The present invention relates to a cyanated perylene compound of the formula I in which one of the Z substituents and one of the Z* substituents are cyano and the other Z substituent and the other Z* substituent are each independently CO2R9, CONR10R11, optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or C6-C14-aryl, where R9, R10 and R11 are each as defined in the claims; and mixtures thereof. The present invention further relates to a composition comprising a cyanated perylene compound of the formula I or mixtures thereof and to a process for preparation thereof; to color converters comprising at least one polymer as matrix material and at least one cyanated perylene compound or mixtures thereof or a composition comprising at least one cyanated perylene compound or mixtures thereof as fluorescent dye; to the use of these color converters and to lighting devices comprising at least one LED and at least one color converter.

Lateral Fusion of Chemical Vapor Deposited N = 5 Armchair Graphene Nanoribbons

Bottom-up synthesis of low-bandgap graphene nanoribbons with various widths is of great importance for their applications in electronic and optoelectronic devices. Here we demonstrate a synthesis of N = 5 armchair graphene nanoribbons (5-AGNRs) and their lateral fusion into wider AGNRs, by a chemical vapor deposition method. The efficient formation of 10- and 15-AGNRs is revealed by a combination of different spectroscopic methods, including Raman and UV-vis-near-infrared spectroscopy as well as by scanning tunneling microscopy. The degree of fusion and thus the optical and electronic properties of the resulting GNRs can be controlled by the annealing temperature, providing GNR films with optical absorptions up to ～2250 nm.

Probing Diels-Alder reactivity on a model CNT sidewall

We have synthesized a cycloparaphenylene containing a perylene motif that is a model for a carbon nanotube sidewall. The reactivity of the sidewall model towards a Diels-Alder reaction using a masked acetylene was examined and similar reactivity was observed between the macrocyclic and planar substrate. This study suggests that a Diels-Alder reaction is a viable method for carbon nanotube growth using an appropriate template.

Electrophilic substitution of two monohomoperylenes and perylene

Various types of electrophilic substitution of monohomoperylene (1) and its 11,11-difluoro derivative (2) have been studied, viz, bromination, nitration, acylation, formylation and sulfonation.Bromination with N-bromosuccinimide (NBS) of 1 in dichloromethane leads to initial substitution mainly at the α position 2 and 10, i.e., of the annuleno moiety, followed by further substitution of the β positions 4 and 8 of the same moiety, and of the α positions 2' and 10' of the naphthaleno moiety.Reaction of 1 with 5.0 mol-equiv. of NBS yields 2,4,8,10,2'-pentabromo-1 in 46percent yield.Sulfonation of 1 with SO3 in dichloromethane using 1.2 mol-equiv. of dioxane as reactivity moderator leads to the formation of 1-2-sulfonic acid (1-2-S), 1-2,10-S2, and the intermediate ? complex 6.Sulfonation of the 11,11-difluoro derivative 2 leads to the formation of 2-2-S, 2-2,10-S2 and 2-2,10-disulfonic anhydride (7), together with small amounts of 2-2,2'-S2 or/and 2-2,10'-S2.The other types of electrophilic substitution of 1 and 2 studied were found to proceed similarly, in that the initial substitution occurs at the 2-position and the subsequent one at the 10-position, i.e., peri to the primarily introduced substituent.The chemical behaviour (i.e., the substitution pattern and relative reactivity) of the two monohomoperylenes 1 and 2 have been compared with that of 1,6-methanoannulene (3), its 11,11-difluoro derivative (4), and perylene (5).For example, the sulfonation reactivity ratio of the naphthalene to the annuleno moiety is significantly greater for 2 than 1, as predicted on the basis of the higher sulfonation reactivity of 3 compared to 4.