Cationic mercaptopyridine-substituted phthalocyanine/MCM-41: an efficient photocatalyst for visible-light synthesis of juglone
Bibliographic record
Abstract
No abstract is available for this record. The assistant can identify its topic from the title, but cannot infer the study’s results.
Source: Not provided · Quality: missing
Research context
OpenAlex topics: Bioactive Compounds and Antitumor Agents · Porphyrin and Phthalocyanine Chemistry · Organic Chemistry Cycloaddition Reactions
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (56)
Show source-provided references
1. Rahman MM, Islam MR, Akash S, Shohag S, Ahmed L, Supti FA et al (2022) Naphthoquinones and derivatives as potential anticancer agents: an updated review. Chem Biol Interact 368:110198. https://doi.org/10.1016/j.cbi.2022.11019810.1016/j.cbi.2022.110198 ↗
2. Jayaram K, Prasad MNV (2007) Rapid in vitro multiplication of Drosera indica L.: a vulnerable, medicinally important insectivorous plant. Plant Biotechnol Rep 1:79–84. https://doi.org/10.1007/s11816-007-0014-710.1007/s11816-007-0014-7 ↗
3. Durán AG, Chinchilla N, Simonet AM, Gutiérrez MT, Bolívar J, Valdivia MM, Molinillo JMG, Macías FA (2023) Biological activity of naphthoquinones derivatives in the search of anticancer lead compounds. Toxins 15:348. https://doi.org/10.3390/toxins1505034810.3390/toxins15050348 ↗
4. Kumagai Y, Shinkai Y, Miura T, Cho AK (2012) The chemical biology of naphthoquinones and its environmental implications. Annu Rev Pharmacol Toxicol 52:221–247. https://doi.org/10.1146/annurev-pharmtox-010611-13451710.1146/annurev-pharmtox-010611-134517 ↗
5. Ertik O, Onul N, Asgarova K, Yanardağ R (2024) Synthesis, molecular docking, some metabolic enzyme inhibition properties, and antioxidant activity studies of 1,4-naphthoquinones. Russ J Bioorg Chem 50:1001–1015. https://doi.org/10.1134/S106816202403026910.1134/S1068162024030269 ↗
6. Ortiz-Pérez E, Rivera G, Salas CO, Zarate-Ramos JJ, Trofymchuk OS, Hernandez-Soberanis L, Perales-Flores JD, Vázquez K (2021) Natural and synthetic naphthoquinones as potential anti-infective agents. Curr Top Med Chem 21(22):2046–2069. https://doi.org/10.2174/156802662166621091512134810.2174/1568026621666210915121348 ↗
7. Anaissi-Afonso L, Oramas-Royo S, Ayra-Plasencia J, Martín-Rodríguez P, García-Luis J, Lorenzo-Castrillejo I, Fernández-Pérez LF, Estévez-Braun A, Machín F (2018) Lawsone, juglone, and β-lapachone derivatives with enhanced mitochondrial-based toxicity. ACS Chem Biol 13(8):1950–1957. https://doi.org/10.1021/acschembio.8b0030610.1021/acschembio.8b00306 ↗
8. Cardoso SH, de Oliveira CR, Guimarães AS, Nascimento J, dos Santos Carmo JDO, de Souza Ferro JN et al (2018) Synthesis of newly functionalized 1,4-naphthoquinone derivatives and their effects on wound healing in alloxan-induced diabetic mice. Chem Biol Interact 291:55–64. https://doi.org/10.1016/j.cbi.2018.06.00710.1016/j.cbi.2018.06.007 ↗
9. Braasch-Turi M, Crans DC (2020) Synthesis of naphthoquinone derivatives: menaquinones, lipoquinones and other vitamin K derivatives. Molecules 25(19):4477. https://doi.org/10.3390/molecules2519447710.3390/molecules25194477 ↗
10. Sreekanth R, Prasanthkumar KP, Sunil Paul MM, Aravind UK, Aravindakumar CT (2013) Oxidation reactions of 1- and 2-naphthols: an experimental and theoretical study. J Phys Chem A 117(44):11261–11270. https://doi.org/10.1021/jp408135510.1021/jp4081355 ↗
11. Sagar R, Shankar U, Khanna A, Singh K, Tiwari G (2023) Recent advances in the synthesis of 2-hydroxy-1,4-naphthoquinone (lawsone) derivatives. SynOpen 7(4):619–651. https://doi.org/10.1055/a-2187-383510.1055/a-2187-3835 ↗
12. Yang C, Wang H, Xie P (2025) Recent advances in visible-light-driven photocatalytic oxidation reactions in water. Chemsuschem 18(4):e202401915. https://doi.org/10.1002/cssc.20240191510.1002/cssc.202401915 ↗
13. Yang X, Zhang S, Li P, Gao S, Cao R (2020) Visible-light-driven photocatalytic selective organic oxidation reactions. J Mater Chem A 8(40):20897–20924. https://doi.org/10.1039/D0TA05485B10.1039/D0TA05485B ↗
14. Bokaei F, Rahimi R, Rabbani M (2024) Photodegradation of 1,5-DHN to juglone as a biocompatible compound, using a metalloporphyrin-based mixed metal–metal organic framework: synthesis, characterization, and photocatalytic behavior. J Nanopart Res 26(10):232. https://doi.org/10.1007/s11051-024-06138-510.1007/s11051-024-06138-5 ↗
15. Blanchard V, Asbai Z, Cottet K, Boissonnat G, Port M, Amara Z (2020) Continuous flow photo-oxidations using supported photocatalysts on silica. Org Process Res Dev 24(5):822–826. https://doi.org/10.1021/acs.oprd.9b0042010.1021/acs.oprd.9b00420 ↗
16. Lancel M, Zimberlin P, Gomez C, Port M, Khrouz L, Monnereau C, Amara Z (2023) Self-sensitized photooxidation of naphthols to naphthoquinones and the use of naphthoquinones as visible light photocatalysts in batch and continuous flow reactors. J Org Chem 88(10):6498–6508. https://doi.org/10.1021/acs.joc.2c0301410.1021/acs.joc.2c03014 ↗
17. Neves CMB, Filipe OMS, Mota N, Santos SAO, Silvestre AJD, Santos EBH, Neves MGPMS, Simões MMQ (2019) Photodegradation of metoprolol using a porphyrin as photosensitizer under homogeneous and heterogeneous conditions. J Hazard Mater 370:13–23. https://doi.org/10.1016/j.jhazmat.2018.11.05510.1016/j.jhazmat.2018.11.055 ↗
18. Gök HZ, Gök Y, Yılmaz MK (2020) Oxidation of benzyl alcohol by novel peripherally and non-peripherally modular C2-symmetric diol substituted cobalt (II) phthalocyanines. Appl Organomet Chem 34(8):e566910.1002/aoc.5669 ↗
19. Patel DP, Patel VK, Singh SK (2024) Rose bengal photocatalyzed expeditious multicomponent synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under visible light irradiation. J Heterocycl Chem 61(9):1455–1461. https://doi.org/10.1002/jhet.486810.1002/jhet.4868 ↗
20. Martínez-Edo G, Balmori A, Pontón I, Martí del Rio A, Sánchez-García D (2018) Functionalized ordered mesoporous silicas (MCM-41): synthesis and applications in catalysis. Catalysts 8(12):617. https://doi.org/10.3390/catal812061710.3390/catal8120617 ↗
21. Szymczak J, Kryjewski M (2022) Porphyrins and phthalocyanines on solid-state mesoporous matrices as catalysts in oxidation reactions. Materials 15:2532. https://doi.org/10.3390/ma1507253210.3390/ma15072532 ↗
22. Xu S, Ding Y, Du J, Zhu Y, Liu G, Wen Z, Liu X, Shi Y, Gao H, Sun L, Li F (2022) Immobilization of iron phthalocyanine on pyridine-functionalized carbon nanotubes for efficient nitrogen reduction reaction. ACS Catal 12:5502–5509. https://doi.org/10.1021/acscatal.2c0018810.1021/acscatal.2c00188 ↗
23. Polyakov MS, Basova TV, Göksel M, Şenocak A, Demirbaş E, Durmuş M, Kadem B, Hassan A (2017) Effect of covalent and non-covalent linking of zinc(II) phthalocyanine functionalised carbon nanomaterials on the sensor response to ammonia. Synth Met 227:78–86. https://doi.org/10.1016/j.synthmet.2017.02.02410.1016/j.synthmet.2017.02.024 ↗
24. Bouanis FZ, Bensifia M, Florea I, Mahouche-Chergui S, Carbonnier B, Grande D, Léonard C, Yassar A, Pribat D (2021) Non-covalent functionalization of single walled carbon nanotubes with Fe-/Co-porphyrin and Co-phthalocyanine for field-effect transistor applications. Org Electron 96:106212. https://doi.org/10.1016/j.orgel.2021.10621210.1016/j.orgel.2021.106212 ↗
25. Li J, Guo L, Shi J (2010) Stepwise in situ synthesis and characterization of metallophthalocyanines/mesoporous matrix SBA-15 composites. Phys Chem Chem Phys 12:5109–5114. https://doi.org/10.1039/B925431E10.1039/B925431E ↗
26. Gök Y, Erdem R, Gök H Z (2025) Photocatalytic selective oxidation of 1-naphthol under red light using SBA-15-supported zinc phthalocyanine. J Photochem Photobiol A Chem 116640. https://doi.org/10.1016/j.jphotochem.2025.11664010.1016/j.jphotochem.2025.116640 ↗
27. Gök HZ, Erdem R, Gök Y (2025) Selective oxidation of benzylic alcohols to aldehydes by C2-symmetric diol substituted cobalt phthalocyanine-mesoporous silica nanostructure. Inorg Chem Commun 174:113961. https://doi.org/10.1016/j.inoche.2025.11396110.1016/j.inoche.2025.113961 ↗
28. Ganschow M, Wöhrle D, Schulz-Ekloff G (1999) Incorporation of differently substituted phthalocyanines into the mesoporous molecular sieve Si-MCM-41. J Porphyrins Phthalocyanines 3:299–309. https://doi.org/10.1002/(SICI)1099-1409(199904)3:4%3c299::AID-JPP134%3e3.0.CO;2-R10.1002/(SICI)1099-1409(199904)3:4<299::AID-JPP134>3.0.CO;2-R ↗
29. Gök Y, Donmez S, Erdem R, Gök HZ (2025) Green photooxidation of 1-naphthol using a zinc phthalocyanine-loaded MCM-41 heterogeneous catalyst. ChemPlusChem 90(8):e202500207. https://doi.org/10.1002/cplu.20250020710.1002/cplu.202500207 ↗
30. Zanjanchi MA, Ebrahimian A, Arvand M (2010) Sulphonated cobalt phthalocyanine–MCM-41: an active photocatalyst for degradation of 2,4-dichlorophenol. J Hazard Mater 175:992–1000. https://doi.org/10.1016/j.jhazmat.2009.10.10810.1016/j.jhazmat.2009.10.108 ↗
31. Pereira JB, Carvalho EF, Faustino MA, Fernandes R, Neves MG, Cavaleiro JA, Tome JP et al (2012) Phthalocyanine thio-pyridinium derivatives as antibacterial photosensitizers. Photochem Photobiol 88:537–547. https://doi.org/10.1111/j.1751-1097.2012.01113.x10.1111/j.1751-1097.2012.01113.x ↗
32. Perrin DD, Armarego WL, Perrin DR (1988) Purification of laboratory chemicals, 3rd edn. Pergamon, Oxford, UK
33. Yener HB, Yılmaz M, Deliismail Ö, Özkan SF, Helvacı ŞŞ (2017) Clinoptilolite supported rutile TiO2 composites: synthesis, characterization, and photocatalytic activity on the degradation of terephthalic acid. Sep Purif Technol 173:17–26. https://doi.org/10.1016/j.seppur.2016.09.01010.1016/j.seppur.2016.09.010 ↗
34. Gök HZ, Demir H (2015) A study of interfacial adsorption isotherm at divided interface for novel macrocycles in solvent extraction. J Incl Phenom Macrocyclic Chem 81:95–104. https://doi.org/10.1007/s10847-014-0438-y10.1007/s10847-014-0438-y ↗
35. Turchi CS, Ollis DF (1990) Photocatalytic degradation of organic water contaminants: mechanisms involving hydroxyl radical attack. J Catal 122:178–192. https://doi.org/10.1016/0021-9517(90)90269-P10.1016/0021-9517(90)90269-P ↗
36. Yin Y, Zhang X, Jiang B et al (2024) Catalytic degradation of rhodamine B by α-DMACoPc/TiO₂/MIL-101(Fe) enhanced catalytic system. J Nanopart Res 26:217. https://doi.org/10.1007/s11051-024-06123-y10.1007/s11051-024-06123-y ↗
37. Misir M, Bilgin A, Doyduk D et al (2025) Novel polymer supported phthalocyanine nanosensors and analytical application. Top Catal. https://doi.org/10.1007/s11244-025-02072-510.1007/s11244-025-02072-5 ↗
38. Tauc J (1968) Optical properties and electronic structure of amorphous Ge and Si. Mater Res Bull 3:37–46. https://doi.org/10.1016/0025-5408(68)90023-810.1016/0025-5408(68)90023-8 ↗
39. Nikoorazm M, Ghorbani-Choghamarani A, Noori N, Tahmasbi B (2016) Palladium 2-mercapto-N-propylacetamide complex anchored onto MCM-41 as efficient and reusable nanocatalyst for Suzuki, Stille and Heck reactions and amination of aryl halides. Appl Organomet Chem 30:843. https://doi.org/10.1002/aoc.351210.1002/aoc.3512 ↗
40. Xie H, Liu H, Wang M, Pan H, Gao C (2020) L-tyrosine-Pd complex supported on Fe₃O₄ magnetic nanoparticles: a new catalyst for C-C coupling and synthesis of sulfides. Appl Organomet Chem 34:e5256. https://doi.org/10.1002/aoc.525610.1002/aoc.5256 ↗
41. Zhao XS, Lu GQ, Hu X (2000) Characterization of the structural and surface properties of chemically modified MCM-41 material. Microporous Mesoporous Mater 41:37–47. https://doi.org/10.1016/S1387-1811(00)00262-610.1016/S1387-1811(00)00262-6 ↗
42. Pasricha S, Gahlot P, Mittal K, Rai D, Avasthi N, Kaur H, Rai S (2022) Functionalized MCM-41: versatile catalysts for organic transformations. ChemSelect 7:e202103674. https://doi.org/10.1002/slct.20210367410.1002/slct.202103674 ↗
43. Ke X, Wu Z, Lin J, Wang F, Li P, Xu R, Zhang D et al (2020) A rapid analytical method for the specific surface area of amorphous SiO2 based on X-ray diffraction. J Non-Cryst Solids 531:119841. https://doi.org/10.1016/j.jnoncrysol.2019.11984110.1016/j.jnoncrysol.2019.119841 ↗
44. Bakar RA, Yahya R, Gan SN (2016) Production of high purity amorphous silica from rice husk. Procedia Chem 19:189–195. https://doi.org/10.1016/j.proche.2016.03.09210.1016/j.proche.2016.03.092 ↗
45. Sing KSW (1995) Physisorption of nitrogen by porous materials. J Porous Mater 2:5–8. https://doi.org/10.1007/BF0048656410.1007/BF00486564 ↗
46. Silva DPS, Solano JRS, Sousa LV et al (2021) Modification of MCM-41 type structures by carbon deposition and acid washing for CO2 adsorption. J Sol-Gel Sci Technol 97:382–392. https://doi.org/10.1007/s10971-020-05432-710.1007/s10971-020-05432-7 ↗
47. Zou W, Liu Y, Song C, Lin H, Huang H, Ye W, Zhang S et al (2022) In situ reduction of PdO encapsulated in MCM-41 to Pd(0) for dehydrogenation of formic acid. Int J Hydrogen Energy 47:28518–28529. https://doi.org/10.1016/j.ijhydene.2022.06.19010.1016/j.ijhydene.2022.06.190 ↗
48. Anwander R, Nagl I, Widenmeyer M, Engelhardt G, Groeger O, Palm C, Röser T (2000) Surface characterization and functionalization of MCM-41 silicas via silazane silylation. J Phys Chem B 104:3532–3544. https://doi.org/10.1021/jp993108d10.1021/jp993108d ↗
49. Cyza M, Gut A, Łapok Ł, Solarski J, Knyukshto V, Kępczyński M, Nowakowska M (2018) Iodinated zinc phthalocyanine–the novel visible-light activated photosensitizer for efficient generation of singlet oxygen. J Photochem Photobiol A Chem 358:265–273. https://doi.org/10.1016/j.jphotochem.2018.03.03010.1016/j.jphotochem.2018.03.030 ↗
50. Lü CX, Zhan GP, Chen K, Liu ZK, Wu CD (2020) Anchoring Zn-phthalocyanines in the pore matrices of UiO-67 to improve highly the photocatalytic oxidation efficiency. Appl Catal B Environ 279:119350. https://doi.org/10.1016/j.apcatb.2020.11935010.1016/j.apcatb.2020.119350 ↗
51. Chen XF, Ng DK (2021) Β-cyclodextrin-conjugated phthalocyanines as water-soluble and recyclable sensitisers for photocatalytic applications. Chem Commun 57:3567–3570. https://doi.org/10.1039/D1CC00713K10.1039/D1CC00713K ↗
52. Song Z, Liu J, Hu Y, Li S, Zhang X, Ma L, Zhang Q et al (2023) Solvent-controlled selective photocatalytic oxidation of benzyl alcohol over Ni/C/TiO2. Catal Commun 176:106628. https://doi.org/10.1016/j.catcom.2023.10662810.1016/j.catcom.2023.106628 ↗
53. Aguillón AR, Leão RA, de Oliveira KT, Brocksom TJ, Miranda LS, de Souza RO (2020) Process intensification for obtaining a cannabidiol intermediate by photo-oxygenation of limonene under continuous-flow conditions. Org Process Res Dev 24:2017–2024. https://doi.org/10.1021/acs.oprd.0c0013110.1021/acs.oprd.0c00131 ↗
54. Takizawa SY, Aboshi R, Murata S (2011) Photooxidation of 1,5-dihydroxynaphthalene with iridium complexes as singlet oxygen sensitizers. Photochem Photobiol Sci 10:895–903. https://doi.org/10.1039/C0PP00265H10.1039/C0PP00265H ↗
55. Yang B, Chen Y, Shi J (2019) Mesoporous silica/organosilica nanoparticles: synthesis, biological effect and biomedical application. Mater Sci Eng R Rep 137:66–105. https://doi.org/10.1016/j.mser.2019.01.00110.1016/j.mser.2019.01.001 ↗
56. Sun T, Zhang YS, Pang B, Hyun DC, Yang M, Xia Y (2014) Engineered nanoparticles for drug delivery in cancer therapy. Angew Chem Int Ed 53:12320–12364. https://doi.org/10.1002/anie.20140303610.1002/anie.201403036 ↗