35337-20-3

Usage

Uses

Used in Chemical Industry:
1-Nitroperylene is used as a raw material for the production of dyes and pigments, leveraging its chemical properties to impart color and stability to these products.
Used in Rubber and Agricultural Chemicals Manufacturing:
1-Nitroperylene serves as a key component in the manufacture of rubber chemicals, contributing to the enhancement of rubber's performance characteristics. In agricultural chemicals, it plays a role in the development of products designed to improve crop protection and yield.
Used as a Stabilizer in Explosives:
1-Nitroperylene is utilized as a stabilizer in explosives to ensure their safe and controlled detonation, highlighting its importance in the explosives industry.
However, due to its hazardous nature, 1-Nitroperylene can cause irritation to the skin, eyes, and respiratory system, necessitating the use of proper safety measures and protective equipment during its handling. Moreover, it is toxic to aquatic organisms and poses a risk of long-term environmental harm, underscoring the need for careful management and disposal to mitigate ecological impacts.

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

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Photoinduced Charge Separation in a Donor-Spacer-Acceptor Dyad with N-Annulated Perylene Donor and Methylviologen Acceptor

The first donor-acceptor species in which a strongly emissive N-annulated perylene dye is connected to a methylviologen electron acceptor unit via its macrocyclic nitrogen atom, is prepared by a stepwise, modular procedure. The absorption spectra, redox behavior, spectroelectrochemistry and photophysical properties of this dyad and of its model species are investigated, also by pump-probe fs transient absorption spectroscopy. Photoinduced oxidative electron transfer from the excited state of the dyad, centered on the N-annulated perylene subunit, to the appended methyviologen electron acceptor takes place in a few ps. The charge-separated species recombines in 19 ps. Our results indicate that N-annulated perylene can be connected to functional units by taking advantage of the macrocyclic nitrogen, an option never used until now, without losing their properties, so opening the way to new designing approaches. Time for a NAP: For the first time a strongly emissive N-annulated perylene (NAP) dye is connected to an electron acceptor subunit by its macrocyclic nitrogen. This molecular motif does not alter the intrinsic properties of the NAP species, and photoinduced charge separation is obtained with a time constant of 5 ps, with the charge-separated state recombining in 19 ps. New ways for designing light-active multicomponent species containing NAP are proposed.

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.

Spiro Rhodamine-Perylene Compact Electron Donor-Acceptor Dyads: Conformation Restriction, Charge Separation, and Spin-Orbit Charge Transfer Intersystem Crossing

Spiro rhodamine (Rho)-perylene (Pery) electron donor-acceptor dyads were prepared to study the spin-orbit charge transfer intersystem crossing (SOCT-ISC) in these rigid and sterically congested molecular systems. The electron-donor Rho (lactam form) moiety is attached via the N-C bond to the electron acceptor at either 1- or 3-position of the Pery moiety (Rho-Pery-1 and Rho-Pery-3). Severe torsion of the Pery moiety in Rho-Pery-1 was observed. The fluorescence of the two dyads is significantly quenched in polar solvents, and the singlet oxygen quantum yields (φδ) are strongly dependent on solvent polarity (4-36%). Femtosecond transient absorption spectra demonstrate that charge separation (CS) takes 0.51 ps in Rho-Pery-1 and 5.75 ps in Rho-Pery-3, and the charge recombination (CR)-induced ISC is slow (>3 ns). Nanosecond transient absorption spectra indicate that the formation of triplet states via SOCT-ISC takes 24-75 ns for Rho-Pery-1 and 6-15 ns for Rho-Pery-3, and the distorted π-framework of the Pery moiety results in a shorter triplet lifetime of 19.9 vs 291 μs for the planar analogue. Time-resolved electron paramagnetic resonance spectroscopy confirms the SOCT-ISC mechanism.

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.

A kind of star-shaped fluorescent molecule and its preparation method and application (by machine translation)

The invention belongs to the field of organic photoelectric technology, discloses a star-shaped fluorescent molecule and its preparation method and application. The invention star fluorescence molecule shown in the following formula: R1 For the C1 - 30 alkyl, C3 - 30 cycloalkyl, C6 - 60 aromatic hydrocarbyl or C7 - 60 aromatic heterocyclic radical. The invention also provides a method for the preparation of star-shaped fluorescent molecules and in organic electronic display in the field of application, is especially suitable for preparing light-emitting diode device of the luminescent layer. The invention star fluorescence molecule, fluorescence quantum yield of the luminescent material and the carrier transmission capacity, to obtain a high efficiency and stable performance of the device; has good thermal stability; space structure can effectively inhibit the fluorescence quenching; and relatively high molecular weight make it have good solubility, soluble in common organic solvent, suitable for solution processing and ink-jet printing, can form a dense film, to prepare the luminescent layer, favorable to the preparation of excellent appearance of the electroluminescent device. (by machine translation)

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.

PHOTOSENSITIVE DYE AND DYE MIXTURE COMPRISING THE SAME

Photosensitive dye has a structure represented by formula (I). The photosensitive dye has better solubility and a maximum absorption wavelength range of 450 nm to 550 nm, and is used to combine with porphyrin dyes.

Seeded Supramolecular Polymerization in a Three-Domain Self-Assembly of an N-Annulated Perylenetetracarboxamide

The three-domain cooperative supramolecular polymerization of 1, together with the lag time in which the monomeric species remains inactive, allows seeded supramolecular polymerization to be performed. The kinetic experiments demonstrate that only seeds based on the intermediate aggregate are able to propagate the supramolecular polymerization of 1 from their active sites. The results presented herein constitute a new example of kinetically controlled supramolecular systems and contribute to expanding knowledge about the structural requirements of a self-assembling molecule to experience seeded supramolecular polymerization.