35337-20-3

Basic information

• Product Name: 1-NITROPERYLENE
• Synonyms: 1-NITROPERYLENE
• CAS NO: 35337-20-3
• Molecular Formula: C₂₀H₁₁NO₂
• Molecular Weight: 301.34
• Mol File: 35337-20-3.mol
• Article Data: 22

Chemical Properties

• Melting Point: 210 °C(Solv: benzene (71-43-2); cyclohexane (110-82-7))
• Boiling Point: 533.5°C at 760 mmHg
• Flash Point: 265.4°C
• Appearance: /
• Density: 1.429g/cm³
• Vapor Pressure: 6.33E-11mmHg at 25°C
• Refractive Index: 1.901
• CAS DataBase Reference: 1-NITROPERYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-NITROPERYLENE(35337-20-3)
• EPA Substance Registry System: 1-NITROPERYLENE(35337-20-3)

Safety Data

• Hazardous Substances Data: 35337-20-3(Hazardous Substances Data)

Usage

General Description

1-Nitroperylene is a yellow crystalline solid and a derivative of perylene, a polycyclic aromatic hydrocarbon. It is primarily used as a raw material in the production of dyes, pigments, and other chemicals. 1-Nitroperylene is also used in the manufacture of rubber chemicals, agricultural chemicals, and as a stabilizer in explosives. It is considered a hazardous substance and can cause irritation to the skin, eyes, and respiratory system upon prolonged or repeated exposure. As such, proper safety measures and protective equipment should be used when handling this chemical. Additionally, 1-Nitroperylene is known to be toxic to aquatic organisms and may cause long-term adverse effects in the environment.

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

Upstream product

• 20589-63-3 3-Nitroperylene 
• 198-55-0 PERYLENE 

Downstream Products

• 1053611-34-9 diethyl 7-nitrobenzo[g,h,i]perylene-1,2-dicarboxylate 
• 31473-75-3 perilo[1,12-b,c,d]thiophene 
• 35337-22-5 1-hydrophenanthrene[1,10,9,8-cdefg]carbazole 
• 1053611-33-8 perilo[1,12-b,c,d]selenophene 
• 35337-21-4 perylene-1-amine 

Relevant articles and documents

Infinite Polyiodide Chains in the Pyrroloperylene–Iodine Complex: Insights into the Starch–Iodine and Perylene–Iodine Complexes

We report the preparation and X-ray crystallographic characterization of the first crystalline homoatomic polymer chain, which is part of a semiconducting pyrroloperylene–iodine complex. The crystal structure contains infinite polyiodide I∞δ?. Interestingly, the structure of iodine within the insoluble, blue starch–iodine complex has long remained elusive, but has been speculated as having infinite chains of iodine. Close similarities in the low-wavenumber Raman spectra of the title compound and starch–iodine point to such infinite polyiodide chains in the latter as well.

Synthesis and characterization of phenanthrocarbazole-diketopyrrolopyrrole copolymer for high-performance field-effect transistors

In this study, we successfully designed and synthesized a novel phenanthro[1,10,9,8-c,d,e,f,g]carbazole (PCZ)-based copolymer poly[N-(2-octyldodecyl)-4,8-phenanthro[1,10,9,8-c,d,e,f,g]carbazole-alt-2, 5-dihexadecyl-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione] (PPDPP) with an extended π-conjugation along the vertical orientation of polymer main chain. This polymer exhibited excellent solubility in common solvent and high thermal stability, owning good properties for solution-processed field-effect transistors (FETs). Besides, absorption spectra demonstrated that annealing PPDPP thin films led to obviously red-shifted maxima, indicating the formations of aggregation or orderly π-π stacking in their solid-state films. X-ray diffraction measurements indicated the crystallinity of PPDPP thin films was enhanced after high temperature annealing, which was favorable for charge transport. The solution-processed PPDPP-based FET devices were fabricated with a bottom-gate/bottom-contact geometry. A high hole mobility of up to 0.30 cm2/Vs and a current on/off ratio above 105 had been demonstrated. These results indicated that the copolymers constructed by this kind of ladder-type cores could be promising organic semiconductors for high-performance FET applications.

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.

Photodeoxygenation of phenanthro[4,5-bcd]thiophene S-oxide, triphenyleno[1,12-bcd]thiophene S-oxide and perylo[1,12-bcd]thiophene S-oxide

Sulfoxides, upon irradiation with ultraviolet (UV) light undergo α-cleavage, hydrogen abstraction, photodeoxygenation, bimolecular photoreduction, and stereo-mutation. The UV irradiation of dibenzothiophene S-oxide (DBTO) yields dibenzothiophene (DBT) as a major product along with ground-state atomic oxygen [O(3P)]. This is a common method for generating O(3P) in solution. The low quantum yield of photodeoxygenation and the requirement of UVA light are drawbacks of using this method. The sulfoxides benzo[b]naphtho-[1,2,d]thiophene S-oxide, benzo[b]naphtho [2,1,d]thiophene S-oxide, benzo[b] phenanthro[9,10-d]thiophene S-oxide, dinaphtho- [2,1-b:1’,2’-d]thiophene S-oxide, and dinaphtho[1,2-b:2’,1’-d]thiophene S-oxide have shown to deoxygenate up to three times faster than DBTO upon UVA irradiation; however, the photodeoxygenation of these sulfoxides does not appear to be limited to the production of O(3P). In this work, phenanthro[4,5-bcd]thiophene S-oxide, triphenyleno[1,12-bcd]thiophene-S-oxide, and perylo[1,12-bcd]thiophene-S-oxide were synthesized and their photodeoxygenation was studied. Phenanthro[4,5-bcd]thiophene-S-oxide, triphenyleno[1,12-bcd]thiophene-S-oxide, and perylo[1,12-bcd]thiophene-S-oxide deoxygenated upon UVA irradiation. However, the common intermediate experiments did not conclusively identify the photodeoxygenation mechanism of these sulfoxides.

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.