3947-76-0

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InChI:InChI=1/C10H10N/c1-11-8-4-6-9-5-2-3-7-10(9)11/h2-8H,1H3/q+1

Upstream product

• 91-22-5 quinoline 
• 74-88-4 methyl iodide 
• 91-63-4 2-methylquinoline 
• 948-43-6 N-methylacridinium iodide 
• 90731-53-6 2-(indol-3-yl)-1-methyl-1,2-dihydroquinoline 

Downstream Products

• 491-34-9 N-methyl-1,2,3,4-tetrahydroquinoline 
• 2739-16-4 3,4-dihydro-2H-quinoline-1-carbaldehyde 
• 1228-70-2 2-(1-methyl-1,4-dihydro-quinolin-4-yl)-2-phenyl-propionitrile 
• 16759-05-0 (1-methyl-1,4-dihydro-quinolin-4-yl)-phenyl-acetonitrile 
• 887-94-5 1-methyl-2-phenyl-1,2-dihydroquinoline 
• 16021-60-6 1-Methyl-1,2-dihydroquinoline 
• 875-63-8 N-methyl-cis-decahydroquinoline 
• 16021-48-0 1-Methyl-4-(4-oxo-2-thioxo-3-ethyl-oxazolidin-5-yliden)-1,4-dihydro-chinolin 
• 16021-33-3 1-Methyl-4-(4-oxo-2-thioxo-3-ethyl-oxazolidinyl-5)-1,4-dihydro-chinolin 
• 16021-43-5 2-diphenylamino-5-(1-methyl-1,4-dihydro-quinolin-4-yl)-thiazol-4-one 
• 606-43-9 1-methyl-2-quinolin-2(1H)-one 
• 132363-86-1 1-methyl-2-trichloromethyl-1,2-dihydroquinoline 
• 99-65-0 meta-dinitrobenzene 

Relevant academic research and scientific papers

Genetically Encoded Dual-Color Light-Up RNA Sensor Enabled Ratiometric Imaging of MicroRNA

MicroRNAs (miRNAs) play essential roles in regulating gene expression and cell fate. However, it remains a great challenge to image miRNAs with high accuracy in living cells. Here, we report a novel genetically encoded dual-color light-up RNA sensor for ratiometric imaging of miRNAs using Mango as an internal reference and SRB2 as the sensor module. This genetically encoded sensor is designed by expressing a splittable fusion of the internal reference and sensor module under a single promoter. This design strategy allows synchronous expression of the two modules with negligible interference. Live cell imaging studies reveal that the genetically encoded ratiometric RNA sensor responds specifically to mir-224. Moreover, the sensor-to-Mango fluorescence ratios are linearly correlated with the concentrations of mir-224, confirming their capability of determining mir-224 concentrations in living cells. Our genetically encoded light-up RNA sensor also enables ratiometric imaging of mir-224 in different cell lines. This strategy could provide a versatile approach for ratiometric imaging of intracellular RNAs, affording powerful tools for interrogating RNA functions and abundance in living cells.

Charge-transfer interactions with N-methylquinolinium ion as electron acceptor

The charge-transfer interactions of N-methylquinolinium ion with aniline and substituted anilines have been investigated by electronic absorption spectroscopy and thermodynamic data determined.The thermodynamic and spectroscopic data has been used to obtain empirical energy parameters from Mulliken's theory.

Photocatalytic degradation of phenolic pollutants using N-methylquinolinium and 9-mesityl-10-methylacridinium salts

The photodegradation of a mixture of phenolic pollutants including: phenol (P), orto-phenylphenol (OPP), 2,4,6-trichlorophenol (TCP) and pentachlorophenol (PCP) was accomplished using two organic cationic photocatalysts, namely N-methylquinolinium (NMQ+) and 9-mesityl-10-methylacridinium (Mes-Acr-Me+) salts, due to their singular photophysical and redox properties. On one hand, NMQ+ exhibits more energetic excited states and accordingly more favorable redox potentials than Mes-Acr-Me+; on the other hand, NMQ+ absorption reaches only up to 380 nm, while Mes-Acr-Me+ extends in the visible up to 480 nm. Evaluation of the efficiency of both photocatalysts, revealed that the highest level of photodegradation was achieved when they were employed at 20% mol. Specifically, with NMQ+, removal of the pollutants was completed within 24 h of irradiation. Even more, irradiation time could be shortened from 24 to 8 h, since high levels of removal were already achieved (93%, 100%, 100% and 82% for P, OPP, TCP and PCP, respectively). Albeit, Mes-Acr-Me+ was not as effective, and best results were obtained using 20% mol upon 24 h of irradiation. Under these conditions, removal of PCP was 80%, while TCP was 40%, OPP 30% and P resulted in the most recalcitrant contaminant with only 10% of removal. Next, NMQ+ and Mes-Acr-Me+ were separately supported onto Zeolite Y, an inert inorganic support (Y-NMQ+ and Y-Mes-Acr-Me+), and elemental analyses revealed a loading of ca. 13% and 15% weight for NMQ+ and Mes-Acr-Me+, respectively. Upon heterogenization, in the case of Y-NMQ+, the extent of removal was lower than the one achieved in the homogeneous photodegradations. On the contrary, performance of Y-Mes-Acr-Me+ improved, because of its enhanced photostability; thus, upon 46 h irradiation, 98%, 80%, 40% and 26% for PCP, TCP, OPP and P, respectively, was achieved. Moreover, their efficiency was maintained upon second use. Steady-state and time-resolved fluorescence quenching revealed that every pollutant was able to quench the singlet excited state of both 1(NMQ+)* and 1(Mes-Acr-Me+)*, with kinetic rate constants in the order of the diffusion limit. Thus, Type I photooxidation happening through the singlet excited state of either photocatalyst was the main operating process in the photodegradation of the studied pollutants.

Synthesis of Tetrahydropyrazolo[4',3':5,6]pyrano[3,4- c ]quinolones by Domino Knoevenagel/Hetero Diels-Alder Reactions

An efficient Lewis acid mediated domino Knoevenagel/hetero Diels-Alder (DKHDA) reaction of pyrazolone derivatives with N -acrylated anthranilic aldehydes was developed, which afforded functionalized tetracyclic tetrahydropyrazolo[4',3':5,6]pyrano[3,4- c ]quinolones. The products were formed in good yields and with excellent regio- and stereoselectivity in favor of the cis-configured isomer.

Synthesis, Structure and Photophysical Properties of a New Class of Inherently Chiral Boron(III) Chelates—The tert-Leucine Complexes

A new family of boron(III) chelates is introduced whereby molecular chirality, confirmed by circular dichroism, is imported during synthesis such that isolation of the diastereoisomers does not require separation procedures. The photophysical properties of two members of the family have been examined: the N,O,O-salicylaldehyde-based derivative shows pronounced intramolecular charge-transfer character in fluid solution and is weakly fluorescent, with a large Stokes shift. The corresponding 2-methylamino-benzaldehyde-derived N,N,O-chelate absorbs and fluoresces in the visible region with a much smaller Stokes shift. Orange fluorescence is also observed for this compound as a cast film. Temperature-dependence studies show that decay of the fluorescent state is weakly activated but emission is less than quantitative at 77 K. Quite rare for boron(III)-based chelates, this derivative undergoes intersystem crossing to form a meta-stable triplet-excited state. X-ray crystal structures are reported for both compounds, along with simulated ECD spectra.

Giant photoconductivity in NMQ[Ni(dmit)2]

The simple molecular salt NMQ[Ni(dmit)2] (NMQ = N-methylquinolinium, dmit = 1,3-dithiol-2-thione-4,5-dithiolate) functions as a diamagnetic insulator with an activation energy Ea(dark) of 0.20 eV. However, at 300 K, it exhibits ca. 40 times higher conductivity (σUV) under UV irradiation [(375±5) nm, 15.7 mWcm -2] than it does under dark conditions (σdark). The ratio σUV/σdark rapidly increases with decreasing temperature and reaches ca. 880 at 200 K. From the temperature dependence of σUV, the activation energy under irradiation Ea(UV) is 0.12 eV. These observations cannot be explained as the result of sample heating during UV irradiation. Rather, the X-ray photoelectron spectra of the sulfur and nickel atoms, the calculated band structure, and the UV/Vis spectra of the salt can all be explained consistently as follows: charge transfer between the Ni(dmit)2 moieties upon exposure to 375 nm UV light induces melting of the charge-ordered state and produces the unusually large photoconductivity of NMQ[Ni(dmit)2].

Multi-state amine sensing by electron transfers in a BODIPY probe

Amines are ubiquitous in the chemical industry and are present in a wide range of biological processes, motivating the development of amine-sensitive sensors. There are many turn-on amine sensors, however there are no examples of turn-on sensors that utilize the amine's ability to react by single electron transfer (SET). We investigated a new turn-on amine probe with a 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) fluorophore. BODIPY fluorescence is first preprogrammed into an off state by internal photoinduced electron transfer (PET) to an electron-deficient quinolinium ring, resulting in fluorescence quenching. At low concentrations of aliphatic amine (0 to 10 mM), this PET pathway is shut down by external SET from the amine to the photoexcited charge-transfer state of the probe and the fluorescence is turned on. At high concentrations of amine (50 mM to 1 M), we observed collisional quenching of the BODIPY fluorescence. The probe is selective for aliphatic amines over aromatic amines, and aliphatic thiols or alcohols. The three molecular processes modulate the BODIPY fluorescence in a multi-mechanistic way with two of them producing a direct response to amine concentrations. The totality of the three molecular processes produced the first example of a multi-state and dose-responsive amine sensor.

Screening of Minimalist Noncanonical Sites in Duplex DNA and RNA Reveals Context and Motif-Selective Binding by Fluorogenic Base Probes

We hypothesize that programmable hybridization to noncanonical nucleic acid motifs may be achieved by macromolecular display of binders to individual noncanonical pairs (NCPs). As each recognition element may individually have weak binding to an NCP, we d

Copper-Catalyzed (4+1) Cascade Annulation of Terminal Alkynes with 2-(Tosylmethyl)anilines: Synthesis of 2,3-Disubstituted Indoles

A novel strategy based on Cu-catalyzed (4+1) cascade annulation of terminal alkynes as one-carbon synthons with 2-(tosylmethyl)anilines has been developed for the expeditious synthesis of 2,3-disubstituted indoles, in which in situ generations of aza-o-quinone methides and alkynyl-copper(I) species are involved. This annulation provides an effective method for the assembly of synthetically and structurally interesting 2,3-disubstituted indoles.

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is