Showing papers on "Pyridine published in 2023"

Tuning Photophysical Properties via Positional Isomerization of the Pyridine Ring in Donor–Acceptor-Structured Aggregation-Induced Emission Luminogens Based on Phenylmethylene Pyridineacetonitrile Derivatives

Abstract: A series of aggregation-induced emission (AIE)-featured phenylmethylene pyridineacetonitrile derivatives named o-DBCNPy ((Z)-3-(4-(di-p-tolylamino)phenyl)-2-(pyridin-2-yl)acrylonitrile), m-DBCNPy ((Z)-3-(4-(di-p-tolylamino)phenyl)-2-(pyridin-3-yl)acrylonitrile), and p-DBCNPy ((Z)-3-(4-(di-p-tolylamino)phenyl)-2-(pyridin-4-yl)acrylonitrile) have been synthesized by tuning the substitution position of the pyridine ring. The linkage manner of the pyridine ring had influences on the molecular configuration and conjugation, thus leading to different photophysical properties. The absorption and fluorescence emission peak showed a bathochromic shift when the linking position of the pyridine ring changed from the meta to the ortho and para position. Meanwhile, o-DBCNPy exhibited the highest fluorescence quantum yield of 0.81 and the longest fluorescence lifetime of 7.96 ns as a neat film among all three isomers. Moreover, non-doped organic light-emitting diodes (OLEDs) were assembled in which the molecules acted as the light-emitting layer. Due to the relatively prominent emission properties, the electroluminescence (EL) performance of the o-DBCNPy-based OLED was superior to those of the devices based on the other two isomers with an external quantum efficiency (EQE) of 4.31%. The results indicate that delicate molecular modulation of AIE molecules could endow them with improved photophysical properties, making them potential candidates for organic photoelectronic devices.

Highly Robust {In2}-Organic Framework for Efficiently Catalyzing CO2 Cycloaddition and Knoevenagel Condensation.

Abstract: To improve the catalytic performance of metal-organic frameworks (MOFs), creating higher defects is now considered as the most effective strategy, which can not only optimize the Lewis acidity of metal ions but also create more pore space to enhance diffusion and mass transfer in the channels. Herein, the exquisite combination of scarcely reported [In2(CO2)5(H2O)2(DMF)2] clusters and 2,6-bis(2,4-dicarboxylphenyl)-4-(4-carboxylphenyl)pyridine (H5BDCP) under solvothermal conditions generated a highly robust nanoporous framework of {[In2(BDCP)(DMF)2(H2O)2](NO3)}n (NUC-65) with nanocaged voids (14.1 Å) and rectangular nanochannels (15.94 Å × 11.77 Å) along the a axis. It is worth mentioning that an In(1) ion displays extremely low tetra-coordination modes after the thermal removal of its associated four solvent molecules of H2O and DMF. Activated {[In2(BDCP)](Br)}n (NUC-65Br), as a defective material because of its extremely unsaturated metal centers, could be generated by bromine ion exchange, solvent exchange, and vacuum drying. Catalytic experiments proved that the conversion of epichlorohydrin with 1 atm CO2 into 4-(chloromethyl)-1,3-dioxolan-2-one catalyzed by 0.11 mol % NUC-65Br could reach 99% at 65 °C within 24 h. Moreover, with the aid of 5 mol % cocatalyst n-Bu4NBr, heterogeneous NUC-65Br owns excellent universal catalytic performance in most epoxides under mild conditions. In addition, NUC-65Br, as a heterogeneous catalyst, exhibits higher activity and better selectivity for Knoevenagel condensation of aldehydes and malononitrile. Hence, this work offers a fresh insight into the design of structure defect cationic metal-organic frameworks, which can be better applied to various fields because of their promoted performance.

TEtraQuinolines: A Missing Link in the Family of Porphyrinoid Macrocycles.

Abstract: Porphyrin contains four inwardly oriented nitrogen atoms. It is arguably the most ubiquitous multifunctional naturally occurring macrocycle that has inspired the design of novel nitrogen-containing heterocycles for decades. While cyclic tetramers of pyrrole, indole, and pyridine have been exploited as macrocycles in this category, quinoline has been largely neglected as a synthon. Herein, we report the synthesis of TEtraQuinoline (TEQ) as a 'missing link' in this N4 macrocycle family. In TEQs, four quinoline units are concatenated to produce an S4-symmetric architecture. TEQs are characterized by a highly rigid saddle shape, wherein the lone-pair orbitals of the four nitrogen atoms are not aligned in a planar fashion. Nevertheless, TEQs can coordinate a series of transition-metal cations (Fe2+, Co2+, Ni2+, Cu2+, Zn2+, and Pd2+). TEQs are inherently fluorescence-silent but become strongly emissive upon protonation or complexation of Zn(II) cations (ϕ = 0.71). TEQ/Fe(II) complexes can catalyze dehydrogenation and oxygenation reactions with catalyst loadings as low as 0.1 mol %.

A room-temperature-stable electride and its reactivity: Reductive benzene/pyridine couplings and solvent-free Birch reductions

Abstract:

Summary

In this work, we report the synthesis of a room-temperature-stable electride (RoSE) reagent, namely K⁺(LiHMDS)e⁻ (1) (HMDS: 1,1,1,3,3,3-hexamethyldisilazide), from accessible starting materials (potassium metal and LiHMDS) via mechanochemical ball milling at 20 mmol scale. Despite its amorphous nature, the presence of anionic electrons in 1, key diagnostic criteria for an electride, was confirmed by both experimental and computational studies. Therefore, by definition, 1 is an electride. Utilizing its anionic electrons, electride reagent 1 exhibited a versatile reactivity profile that includes (1) mediation of C–H activation and C–C coupling of benzene and pyridine and (2) mediation of solvent-free Birch reduction. This work proves the concept of facile mechanochemical synthesis of a room-temperature-stable electride, and it introduces electride 1 to the synthetic chemistry community as a versatile reagent.

Hydrogen‐Bond Regulation of the Microenvironment of Ni(II)‐Porphyrin Bifunctional Electrocatalysts for Efficient Overall Water Splitting

Abstract: Accurately regulating the microenvironment around active sites is an important approach for boosting the overall water splitting performance of bifunctional electrocatalysts, which can drive both the oxygen evolution reaction (OER) and the hydrogen evolution reaction (HER) in the same electrolyte. Herein, pseudo‐pyridine‐substituted Ni(II)‐porphyrins (o‐NiTPyP, m‐NiTPyP, and p‐NiTPyP) with pseudo‐pyridine N‐atoms located at the ortho‐, meta‐, or para‐position are prepared and used as model catalysts for alkaline water splitting. Experimental and theoretical results reveal that the pseudo‐pyridine N‐atom positions can regulate the microenvironment around the active sites and the adsorption free energy of H‐donating substances by affecting the H‐bonding interaction and the NNiN bond angles of active sites, and thus those pseudo‐pyridine‐substituted Ni(II)‐porphyrins deliver better electrocatalytic activity than the Ni(II)‐tetraphenylporphyrin (NiTPP) without pseudo‐pyridine N‐atoms. Among them, m‐NiTPyP on carbon nanotubes delivers the lowest overpotentials of 267 and 138 mV at 10 mA cm−2 for the OER and HER, respectively. Specifically, m‐NiTPyP as bifunctional electrocatalyst in an alkaline electrolyzer requires only 1.62 V to drive efficient overall water splitting at 10 mA cm−2 while remaining durable. This work proposes a new H‐bond‐regulating approach of the microenvironment of electrocatalysts for effectively boosting the overall water splitting activity and deeply understanding its related mechanism.

Design, synthesis, and in vitro anticancer activity of thiophene substituted pyridine derivatives

Abstract: In the present research work, eight novel amide derivatives (5a–h) incorporating thiophene and pyridine moieties were synthesized by using HATU (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium3-oxide hexafluorophosphate, hexafluorophosphate azabenzotriazole tetramethyl uronium) as a reagent for the amide reaction. All the novel samples were characterized by 1H-NMR (proton magnetic resonance), 13C-NMR (carbon magnetic resonance), FT-IR (Fourier transform infrared spectroscopy), and UV-visible spectral techniques. All the amide samples were tested for in vitro cell viability assay and log IC50 values against HeLa, MCF-7, and Hep G2 cell lines after the 24 h of treatment. Compounds 5a, 5b, and 5c showed promising anticancer activity against Hep G2 cell lines when compared with standard drug docetaxel. Three of the synthesized derivatives exhibited high cytotoxicity against Hep G2 cell lines as compared with standard docetaxel. The cytotoxicity of the docetaxel (IC50) was 0.2200, 0.2100, and 0.2250 µM for HeLa, MCF-7, and Hep G2 cell lines at 24 h. Whereas log IC50 values of the 5a, 5b, and 5c derivatives containing active –F (Fluorine), –Cl (Chlorine), –F, Cl (fluorine and chlorine) groups was found to be 0.1298 ± 0.098, 0.1456 ± 0.001, and 0.1647 ± 0.013µM, respectively, against HepG2 cell lines. Rest other compounds showed moderate activity against all the treated cell lines at 24 h. Thiophene substituted pyridine derivatives are a promising candidate for anticancer treatment.

Synthesis of New Pyrazolo[1,5‐ a ]pyrimidines as Potential Antibacterial Agents: In Vitro and In Silico Study

Abstract: In this study, we aimed to establish two new series of pyrazolo[1,5-a]pyrimidines starting from 1H-pyrazole-3,5-diamine. The first series was prepared by reacting 1H-pyrazole-3,5-diamine with the appropriate enaminones in pyridine at 120 °C for 5–6 h to produce 7-arylpyrazolo[1,5-a]pyrimidines in 87–94 % yields. Furthermore, α,β-unsaturated ketones was reacted with 1H-pyrazole-3,5-diamine in ethanolic potassium hydroxide solution at 80 °C for 4 h to produce a second series of regioisomeric 5,7-diarylpyrazolo[1,5-a]pyrimidines in 88–96 % yields. The antibacterial activity of new products was tested against six different bacterial strains. Substituting para-arene units at C5 and/or C7 on the pyrazolo[1,5-a]pyrimidine structure improved efficacy, with electron-releasing substituents having the greatest impact. Some new pyrazolo[1,5-a]pyrimidine were found to be more effective than ciprofloxacin, with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values up to 2.2 and 4.4 μM, respectively. These compounds were deemed to have drug-like properties according to SwissADME and drug-likeness model scores.

Recent Advances in N-Heterocyclic Small Molecules for Synthesis and Application in Direct Fluorescence Cell Imaging

Abstract: Nitrogen-containing heterocycles are ubiquitous in natural products and drugs. Various organic small molecules with nitrogen-containing heterocycles, such as nitrogen-containing boron compounds, cyanine, pyridine derivatives, indole derivatives, quinoline derivatives, maleimide derivatives, etc., have unique biological features, which could be applied in various biological fields, including biological imaging. Fluorescence cell imaging is a significant and effective imaging modality in biological imaging. This review focuses on the synthesis and applications in direct fluorescence cell imaging of N-heterocyclic organic small molecules in the last five years, to provide useful information and enlightenment for researchers in this field.

C3‐Cyanation of Pyridines: Constraints on Electrophiles and Determinants of Regioselectivity

Abstract: Methods for C-H cyanation of pyridines are rare. Here, we report a method for C3-selective cyanation of pyridines by a tandem process with the reaction of an in situ generated dihydropyridine with a cyano electrophile as the key step. The method is suitable for late-stage functionalization of pyridine drugs. The low reduction potential of the electrophile and effective transfer of the nitrile group were found to be essential for the success of this method. We studied the reaction mechanism in detail by means of control experiments and theoretical calculations and found that a combination of electronic and steric factors determined the regioselectivity of reactions involving C2-substituted pyridines.

C-N bond cleavage of primary amine for the synthesis of multi-substituted pyridine and pyrrole derivatives

Abstract: An efficient synthesis of multi-substituted pyridines and pyrroles has been developed from aryl methyl ketones with 1-amino-2-methylpropan-2-ol and 1,2-diamino-2-methylpropane, respectively. The reaction involves one C-N bond cleavage and two new...

Toxicity Study and Binding Analysis of Newly Synthesized Antifungal N-(4-aryl/cyclohexyl)-2-(pyridine-4-yl carbonyl) hydrazinecarbothioamide Derivative with Bovine Serum Albumin

Abstract: The presence of the p-aryl/cyclohexyl ring in the N-(4-aryl/cyclohexyl)-2-(pyridine-4-yl carbonyl) hydrazine carbothioamide derivative (2C) is reported to enhance the antifungal properties when compared to those of itraconazole. Serum albumins present in plasma bind and transport ligands, including pharmaceuticals. This study explored 2C interactions with BSA using spectroscopic methods such as fluorescence and UV-visible spectroscopy. In order to acquire a deeper comprehension of how BSA interacts with binding pockets, a molecular docking study was carried out. The fluorescence of BSA was quenched by 2C via a static quenching mechanism since a decrease in quenching constants was observed from 1.27 × 105 to 1.14 × 105. Thermodynamic parameters indicated hydrogen and van der Waals forces responsible for the BSA–2C complex formation with binding constants ranging between 2.91 × 105 and 1.29 × 105, which suggest a strong binding interaction. Site marker studies displayed that 2C binds to BSA’s subdomains IIA and IIIA. Molecular docking studies were conducted to further comprehend the molecular mechanism of the BSA–2C interaction. The toxicity of 2C was predicted by Derek Nexus software. Human and mammalian carcinogenicity and skin sensitivity predictions were associated with a reasoning level of equivocal, inferring 2C to be a potential drug candidate.

Synthesis, Characterization, Bioactivity Screening and Computational Studies of Diphenyl−malonohydrazides and Pyridines Derivatives

Abstract: A series of new hydrazide (3 a–j) and pyridine (11 a–j) derivatives were synthesized using a convergent synthetic methodology by condensation of malono-di(2-phenylhydrazide) with arylidene malononitrile or arylidene ethyl cyanoacetate derivatives. The synthesized compounds (3, 11 a–j) were characterized using via IR, 1H-, 13C-NMR, and MS spectroscopies as well as elemental analysis. The biological activity of these molecules has been evaluated in vitro against two gram-positive bacteria (Staphylococcus aureus and Streptococcus pneumoniae) and one-gram negative bacteria (Escherichia coli), as well as one fungus (Candida albicans). The results of the bioactive assay revealed that the synthesized pyridine (11 a–j) derivatives had greater antibacterial efficacy than the hydrazide (3 a–j) derivatives and were comparable to the reference drug Augmentin. Furthermore, docking studies against the Staphylococcus aureus dihydrofolate reductase (DHFR) protein revealed that pyridine derivatives (11 a–j) had higher binding interactions affinity (ΔG=−9.59∼−7.69 kcal/mol) than diphenyl−malonohydrazide derivatives (3 a–j), which achieved a binding affinity in the range of (ΔG=−9.65∼−6.77 kcal/mol), supporting the experimental results. Finally, DFT and TD-DFT were used to gain a better understanding of the structure-activity relationship and biological activity of the new synthesized hydrazide/pyridine derivatives.

Organic pH Buffer for Dendrite-Free and Shuttle-Free Zn-I2 Batteries.

Abstract: Aqueous Zn-iodine (I2) batteries are attractive for large-scale energy storage. However, drawbacks include, Zn dendrites, hydrogen evolution reaction (HER), corrosion and, cathode 'shuttle' of polyiodines. Here we report a class of N-containing heterocyclic compounds as organic pH buffers to obviate these. We evidence that addition of pyridine /imidazole regulates electrolyte pH, and inhibits HER and anode corrosion. In addition, pyridine and imidazole preferentially absorb on Zn metal, regulating non-dendritic Zn plating /stripping, and achieving a high Coulombic efficiency of 99.6% and long-term cycling stability of 3,200 h at 2 mA cm-2, 2 mAh cm-2. It is also confirmed that pyridine inhibits polyiodines shuttling and boosts conversion kinetics for I-/I2. As a result, the Zn-I2 full battery exhibits long cycle stability of > 25,000 cycles and high specific capacity of 105.5 mAh g-1 at 10 A g-1. We conclude organic pH buffer engineering is practical for dendrite-free and shuttle-free Zn-I2 batteries.

Visible‐Light Induced Fixation of SO2 into Organic Molecules with Polypyridine Chromium(III) Complexes

Abstract: Incorporation of sulfur dioxide into organic compounds is achieved by a photocatalytic approach using sensitizers made from earth‐abundant chromium(III) ions and visible light leading to sulfones and sulfonamides. We employed three different chromium(III) sensitizers [Cr(ddpd)2]3+, [Cr(bpmp)2]3+ and [Cr(tpe)2]3+ with long excited state lifetimes and different ground and excited state redox potentials as well as varying stability under the reaction conditions (ddpd=N,N’‐dimethyl‐N,N’‐dipyridin‐2‐yl‐pyridine‐2,6‐diamine; bpmp=2,6‐bis(2‐pyridylmethyl)pyridine; tpe=1,1,1‐tris(pyrid‐2‐yl)ethane). Key reaction steps of the catalytic cycles are identified by electrochemical, luminescence quenching, photolysis, laser flash photolysis and catalytic experiments delivering a detailed picture of the challenges in these transformations. The reactivity of the reduced chromium complex was identified as a key property to explain the reaction outcomes. Initial cage escape yield determinations with [Cr(tpe)2]3+ revealed that desired photoreactions occur with unusually high quantum efficiencies, whereas side reactions are almost unproductive.

Room Temperature Intermolecular Dearomatization of Arenes by an Acyclic Iminosilylene.

Abstract: A novel nontransient acyclic iminosilylene (1), bearing a bulky super silyl group (-SitBu3) and N-heterocyclic imine ligand with a methylated backbone, was prepared and isolated. The methylated backbone is the feature of 1 that distinguishes it from the previously reported nonisolable iminosilylenes, as it prevents the intramolecular silylene center insertion into an aromatic C-C bond of an aryl substituent. Instead, 1 exhibits an intermolecular Büchner-ring-expansion-type reactivity; the silylene is capable of dearomatization of benzene and its derivatives, giving the corresponding silicon analogs of cycloheptatrienes, i.e. silepins, featuring seven-membered SiC6 rings with nearly planar geometry. The ring expansion reactions of 1 with benzene and 1,4-bis(trifluoromethyl)benzene are reversible. Similar reactions of 1 with N-heteroarenes (pyridine and DMAP) proceed more rapidly and irreversibly forming the corresponding azasilepins, also with nearly planar seven-membered SiNC5 rings. DFT calculations reveal an ambiphilic nature of 1 that allows the intermolecular aromatic C-C bond insertion to occur. Additional computational studies, which elucidate the inherent reactivity of 1, the role of the substituent effect, and reaction mechanisms behind the ring expansion transformations, are presented.

Pyridinic Nitrogen Modification for Selective Acetylenic Homocoupling on Au(111).

Abstract: On-surface acetylenic homocoupling has been proposed to construct carbon nanostructures featuring sp hybridization. However, the efficiency of linear acetylenic coupling is far from satisfactory, often resulting in undesired enyne products or cyclotrimerization products due to the lack of strategies to enhance chemical selectivity. Herein, we inspect the acetylenic homocoupling reaction of polarized terminal alkynes (TAs) on Au(111) with bond-resolved scanning probe microscopy. The replacement of benzene with pyridine moieties significantly prohibits the cyclotrimerization pathway and facilitates the linear coupling to produce well-aligned N-doped graphdiyne nanowires. Combined with density functional theory calculations, we reveal that the pyridinic nitrogen modification substantially differentiates the coupling motifs at the initial C-C coupling stage (head-to-head vs head-to-tail), which is decisive for the preference of linear coupling over cyclotrimerization.

Synthesis of New Bis(pyrazolo[1,5‐a]pyrimidines) Linked to Different Spacers as Potential MurB Inhibitors

Abstract: An efficient protocol was adopted to efficiently prepare three new series of bis(pyrazolo[1,5‐a]pyrimidines) linked to different spacers. The new bis(pyrazolo[1,5‐a]pyrimidines) were prepared in 80–90 % yields by reacting the respective bis(enaminones) and 4‐(4‐substituted benzyl)‐1H‐pyrazole‐3,5‐diamines in pyridine at reflux temperature for 5–7 h. The new products showed a wide spectrum of antibacterial activity against six different bacterial strains. In general, propane‐ and butane‐linked bis(pyrazolo[1,5‐a]pyrimidines), which are attached to 3‐(4‐methyl‐ or 4‐methoxybenzyl) units, had the best antibacterial activity with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values up to 2.5 and 5.1 μM, respectively. Additionally, the previous products demonstrated promising MurB inhibitory activity with IC50 values up to 7.2 μM.

Evaluation of the anti-proliferative activity of 2-oxo-pyridine and 1′H-spiro-pyridine derivatives as a new class of EGFRWt and VEGFR-2 inhibitors with apoptotic inducers

Abstract: Developing new agents for cancer treatment remains a top priority because it is one of the deadliest worldwide. A new series of 2-oxo-pyridine and 1′H-spiro-pyridine derivatives were designed and synthesized based on an N-(ethyl benzoate) moiety. The structure of the designed derivatives was confirmed by different spectroscopic techniques (FT-IR and NMR) and elemental analysis and then evaluated as antiproliferative against HepG-2 and Caco-2 cell lines compared with Doxorubicin. The spiro-pyridine derivatives 5, 7, and 8 exhibited a remarkably higher activity against Caco-2 cell lines than that of other derivatives. Additionally, these derivatives exhibited activation in the Bax and suppressed Bcl-2 expression with variable degrees. Interestingly, compound 7 showed the lowest cytotoxicity value on Caco-2 cells (IC50 = 7.83 ± 0.50 μM) compared with Doxorubicin (IC50 = 12.49 ± 1.10 μM). Additionally, this compound showed activation of the Bax gene (7.508-fold) and suppressed Bcl-2 (0.194-fold) compared to untreated Caco-2 cells, as revealed by the qRT-PCR technique. Moreover, compound 7 could inhibit EGFR and VEGFR-2 with sub-micromole values of 0.124 μM and 0.221 μM compared with Erlotinib (IC50 = 0.033 μM) and Sorafenib (IC50 = 0.043 μM), respectively. Further, cell cycle and apoptosis analysis demonstrated that compound 7 promoted apoptosis by increasing the apoptosis rate from 1.92 to 42.35% and the S cell accumulation ratio from 31.18 to 42.07% compared to untreated Caco-2 cells. Finally, the most active compound 7 showed good drug-likeness and toxicity profiles. Besides, molecular docking studies were performed to determine the binding mode, which is in agreement with the in vitro results.

Synthesis and Structure–Activity Relationship of 2,6-Disubstituted Thiosemicarbazone Derivatives of Pyridine as Potential Antituberculosis Agents

Abstract: In this study, six new 2,6-disubstituted thiosemicarbazone derivatives of pyridine were synthesized (4–9), and their tuberculostatic activity was evaluated. All of them showed two- to eightfold higher activity (minimum inhibitory concentration (MIC) 0.5–4 µg/mL) against the resistant strain compared with the reference drug. Compounds 5 and 7, which contained the most basic substituents—pyrrolidine and piperidine—in their structure, strongly inhibited the growth of the standard strain (MIC 2 µg/mL). Furthermore, the same derivatives exhibited activity comparable to that of the reference drugs against some types of Gram-positive bacteria (MIC 0.49 µg/mL) and showed no cytotoxicity (IC50 > 50 µg/mL) in HaCaT cells. The zwitterionic structure of each compound was determined using X-ray crystallography. Absorption, distribution, metabolism, and excretion analyses showed that all compounds are good drug candidates. Thus, compounds 5 and 7 were identified as leading structures for further research on antituberculosis drugs with extended effects.

Effects of the Acidic and Textural Properties of Y-Type Zeolites on the Synthesis of Pyridine and 3-Picoline from Acrolein and Ammonia

Abstract: A set of Y-type zeolites with Si/Al atomic ratios between 7–45 were studied as catalysts in the aminocyclization reaction between acrolein and ammonia to produce pyridine and 3-picoline. The catalytic activity tests at 360 °C revealed that the acrolein conversion increased in the order Z45 < ZY34 < ZY7 < ZY17, in agreement with the increase of the total acidity per gram of catalyst. In all cases, pyridine bases and cracking products (acetaldehyde and formaldehyde) were detected in the outflow from the reactor. The total yield of pyridines was inversely proportional to the total acidity for the catalysts, which presented large surface areas and micro- and mesoporosity. The selectivity towards 3-picoline was favored when using catalysts with a Brønsted/Lewis acid sites ratio close to 1. The formation of pyridine occurred more selectively over Lewis acid sites than Brønsted acid sites. The deactivation tests showed that the time on stream of the catalysts depended on the textural properties of zeolites, i.e., large pore volume and large BET area, as evidenced by the deactivation rate constants and the characterization of the spent catalysts. The physicochemical properties of the catalysts were determined by XRD, UV-vis, and Raman spectroscopies, infrared spectroscopy with adsorbed pyridine, N2 physisorption, and SEM-EDXS. After the reaction, the spent catalysts were characterized by XRD, Raman spectroscopy, TGA, and SEM-EDXS, indicating that the uniform deposition of polyaromatic species on the catalyst surface and within the porous system resulted in the loss of activity.