20589-63-3

Usage

Uses

Used in Chemical Production Industry:
3-Nitroperylene is used as an intermediate in the production of pigments, dyes, and other chemicals. Its chemical properties make it a valuable component in the synthesis of various compounds used in different industries.
Used in Environmental Monitoring:
Due to its classification as a hazardous substance and potential environmental pollutant, 3-nitroperylene is also used as a marker for monitoring environmental contamination. Its detection in air, water, or soil samples can indicate the presence of pollutants and help in assessing the environmental impact of industrial activities.

InChI:InChI=1/C20H11NO2/c22-21(23)18-11-10-16-14-7-2-5-12-4-1-6-13(19(12)14)15-8-3-9-17(18)20(15)16/h1-11H

Upstream product

• 198-55-0 PERYLENE 

Downstream Products

• 20492-13-1 3-Aminoperylene 
• 35337-20-3 1-nitroperilene 
• 24471-47-4 3-Methyl-perylen 

Relevant academic research and scientific papers

The effects of 1-and 3-positions substitutions on the photophysical properties of perylene and its application in thiol fluorescent probes

A series of perylene derivatives bearing electron-donating group (amino) and electron-withdrawing group (nitro, maleimide) at the 1- and 3-position have been synthesized. Interestingly, 3-monosubstituted perylenes shown different photophysical properties compared with 1-monosubstituted perylenes. 3-nitroperylene (3-NO) attained 80.62% photoluminescence quantum yield (ΦPL) in toluene which is higher than 3-aminoperylene (3-NH, ΦPL = 71.70%) and 1-aminoperylene (1-NH, ΦPL = 48.04%), but for 1-nitroperylene (1-NO), no fluorescence in any solvent were observed. The calculated ground-state geometries of 3-monosubstituted perylenes actually correspond to nearly planar structures, but the molecules substituted at the 1-position all have a twisted structure. Among them, 3-NO had a great π-conjugated system, resulting in the allowed ππ? fluorescence. In contrast, the twisting structure of 1-NO enhanced nonradiative decay pathways, coupled with the electron-withdrawing effect of the nitro group, which can explain the non-luminescence of 1-NO. Furthermore, the moleculars with maleimide group were used as “off-on” fluorescent probes and successfully used for imaging biothiols in living H1299 lung cancer cells. The fluorescence of probe 2 (substitutes at 3-position of perylene) afforded a 188-fold intensity increase after reaction with thiol which is much higher than (65-fold) probe 1 (substitutes at 1-position) because of the better π-conjugated structure. We envision that the investigation on the effects of substitute at 1-and 3-positions of perylene may be helpful for a rational design and application of highly fluorescent molecule base on perylene.

Perylene-based small molecular fluorescent probe and preparation method and application thereof

The invention belongs to the technical field of sulfhydryl biological small molecule detection, in particular to a perylene-based small molecular fluorescent probe and a preparation method and application thereof. The preparation method comprises the following steps: first performing a nitration reaction on 1-position carbon or 3-position carbon of perylene so as to connect a nitro group, then reducing the nitro group into an amino group, then replacing the amino group with maleic anhydride so as to obtain two small molecular fluorescent probes adopting novel structures, provided by the invention, wherein the two small molecular fluorescent probes adopts the chemical structural formulae shown as a formula (I) or a formula (II). When the small molecular fluorescent probe is combined with a sulfhydryl biological small molecule in a biological cell, green light is emitted, which is significantly different from background blue light of the biological cell; the small molecular fluorescent probe has the advantages of high sensitivity, good selectivity and low biological toxicity; in addition, the preparation process is simple and optimized, and the detection cost of the sulfhydryl biological small molecule is greatly reduced.

PHENANTHRO[1,10,9,8-C,D,E,F,G]CARBAZOLE POLYMERS AND THEIR USE AS ORGANIC SEMICONDUCTORS

The invention relates to novel phenanthro[1,10,9,8-c,d,e,f,g]carbazole polymers, methods and materials for their preparation, their use as semiconductors in organic electronic (OE) devices, and to OE devices comprising these polymers.

Heteroatom-annulated perylenes: Practical synthesis, photophysical properties, and solid-state packing arrangement

(Chemical Equation Presented) A practical strategy for the preparation of a series of heterocyclic annulated perylenes in good yields is presented. UV-vis absorption spectra indicate hypsochromic shift of the absorption maxima relative to the corresponding parent perylene. Single-crystal X-ray diffraction analysis reveals that they all adopt planar conformation, but the solid-state packing arrangements are significantly altered by annulation of various heterocycles.

Abnormal orientation in nitration of anthracene, pyrene, and perylene with pyridinium nitrate. 2-Nitroanthracene and 4-nitropyrene

Nitration by undissociated nitric acid which presumably forms at thermolysis (115°C) of pyridinium nitrate in pyridine selectively proceeds with respect to aromatic substrates and nonselectively with respect to various positions in aromatic rings. Whereas in electrophilic nitration forms a single isomer of mononitro products, the process under study yields two mononitro isomers, and nitration occurs only with polycyclic hydrocarbons containing a butadiene fragment included into neighboring rings (anthracene, naphthacene, pyrene, and perylene). On the contrary, benzene and its derivatives, naphthalene, phenanthrene, and triphenylene are not nitrated. Beside pyridinium nitrate as nitrating agents giving two isomeric mononitro arenes from polycyclic compounds are used tetranitromethane in pyridine and ammonium nitrate in a mixture pyridine-acetic anhydride. The side products of the reaction are biaryls, quinones (in particular, with unusually located carbonyl groups), and dyes containing aci-nitro and oxo groups.

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.

Nitration of Aromatics via Electron Transfer. IV. On the Reaction between Perylene Radical Cation and Nitrogen Dioxide or Nitrite Ion

The electron transfer mechanism for aromatic nitration by nitronium ion involves a crucial step the diffusion-controlled coupling between a radical cation and nitrogen dioxide.We now report that the reaction betwee (perylene).+ hexafluorophosphate or trifluoromethanesulfonate with nitrogen dioxide does not lead to the clean formation of mononitroperylenes.This militates against the possibility of the nitronium ion acting as an electron transfer oxidant in all practical cases of aromatic nitration, perylene being one of the most easily oxidizable aromatics available.These results are in accordance with earliar presented calculations based on the Marcus theory.The observation of the radical cations under conditions of aromatic nitration is suggested to be the result of either homolityc dissociation of the ?-complex under strongly acidic conditions or oxidation by nitrosonium ion impurities. (Perylene).* reacts instaneously with nitrile ion in a 100percent electron transfer process, yielding perylene and dinitrogen tetraoxide.The reaction between the two latter species leads to the formation of mononitroperylenes in excellent yields with high 3-/1- isomer ration in neutral or slightly acidic media or with low 3-/1- ratio under basic conditions or in media of low ionizing power.

Nitration of Polycyclic Aromatic Hydrocarbons by Dinitrogen Tetraoxide. II. Synthetic and Mechanistic Aspects

Treatment of polycyclic aromatic hydrocarbons by dinitrogen tetraoxide in dichloromethane solution leads to the clean production of mononitro derivatives with high positional selectivity in almost quantitative yields.For substrates less reactive than chrysene the addition of catalytic amounts of acid is required for the reaction to proceed at convenient rates.Being very easily performed, the method should be regarded as the best yet found for the synthesis of small amount of these, in many cases, mutagenic mononitro compounds.From studies on relative reactivities, isomer distributions, and the effect of acid, base and nitrosonium ion on the reaction, a mechanism involving initial attack of a novel electrophile, nitrosated dinitrogen tetraoxide, is proposed.The initially formed ?-complex is suggested to be transformed into the nitro ?-complex via a pathway involving radical pairs, thus explaining the observation by others of CIDNP effects on the reaction path of nitrous acid catalyzed nitration, a reaction proposed to follow the same reaction scheme.