Mesoporous silica–supported metalloSalen and metalloSalphen: synthesis and application in heterogeneous catalysis

1. Schiff H (1869) Untersuchungen über Salicinderivate. Justus Liebigs Ann Chem 150:193–200. https://doi.org/10.1002/jlac.1869150020610.1002/jlac.18691500206 ↗

2. Pfeiffer P, Breith E, Lübbe E, Tsumaki T (1933) Tricyclische orthokondensierte Nebenvalenzringe. Justus Liebigs Ann Chem 503:84–130. https://doi.org/10.1002/jlac.1933503010610.1002/jlac.19335030106 ↗

3. Pfeiffer P, Breith E, Lubbe E, Tsumaki T (1932) Thcylische Orthokondesierte Nebenvalenzringe. Annalen Der. Chemie 492:81–127

4. Sani U, Na’ibi HU, Dailami SA (2018) In vitro antimicrobial and antioxidant studies on N-(2- hydroxylbenzylidene) pyridine -2-amine and its M(II) complexes. Nig J Bas App Sci 25:81. https://doi.org/10.4314/njbas.v25i1.1110.4314/njbas.v25i1.11 ↗

5. More MS, Joshi PG, Mishra YK, Khanna PK (2019) Metal complexes driven from Schiff bases and semicarbazones for biomedical and allied applications: a review. Mater Today Chem 14:100195. https://doi.org/10.1016/j.mtchem.2019.10019510.1016/j.mtchem.2019.100195 ↗

6. Yaseen AA, Al-Tikrity ETB, Al-Mashhadan MH et al (2021) An overview: using different approaches to synthesis new Schiff bases materials. JUAPS 15:3–59. https://doi.org/10.37652/juaps.2022.17245310.37652/juaps.2022.172453 ↗

7. Novoa-Ramírez CS, Silva-Becerril A, Olivera-Venturo FL et al (2020) N/N bridge type and substituent effects on chemical and crystallographic properties of Schiff-base (salen/salphen) Niii complexes. Crystals 10:616. https://doi.org/10.3390/cryst1007061610.3390/cryst10070616 ↗

8. Räisänen MT, Nieger M, Slawin AMZ et al (2011) Two- and three-dimensional packing diagrams of M(salophen) complexes. CrystEngComm 13:4701. https://doi.org/10.1039/c0ce00926a10.1039/c0ce00926a ↗

9. Ambroziak K, Szypa M (2007) A synthesis of unsymmetrical chiral salen ligands derived from 2-hydroxynaphthaldehyde and substituted salicylaldehydes. Tetrahedron Lett 48:3331–3335. https://doi.org/10.1016/j.tetlet.2007.03.08210.1016/j.tetlet.2007.03.082 ↗

10. Atwood DA, Harvey MJ (2001) Group 13 compounds incorporating salen ligands. Chem Rev 101:37–52. https://doi.org/10.1021/cr990008v10.1021/cr990008v ↗

11. Ding B, Solomon MB, Leong CF, D’Alessandro DM (2021) Redox-active ligands: recent advances towards their incorporation into coordination polymers and metal-organic frameworks. Coord Chem Rev 439:213891. https://doi.org/10.1016/j.ccr.2021.21389110.1016/j.ccr.2021.213891 ↗

12. Chiari B, Cinti A, Crispu O, et al (2001) Binuclear Co(ii)Co(ii), Co(ii)Co(iii) and Co(iii)Co(iii) complexes of “short” salen homologues derived from the condensation of salicylaldehyde and methanediamine or phenylmethanediamines. Synthesis, structures and magnetism. J Chem Soc, Dalton Trans 3611–3616. https://doi.org/10.1039/b105594c.Electronic supplementary information (ESI) available: Appendix, derivation of the expression for the average magnetic susceptibility of a Co(ii)Co(ii) dimer. See http://www.rsc.org/suppdata/dt/b1/b105594c/10.1039/b105594c. ↗

13. Chiari B, Cinti A, Crispu O, et al (2002) New pentanuclear mixed valence Co( II )–Co( III ) complexes of “short” salen homologues. J Chem Soc, Dalton Trans 4672–4677. https://doi.org/10.1039/B206221F10.1039/B206221F ↗

14. Pasini A, Demartin F, Piovesana O, et al (2000) Novel copper(II) complexes of “short” salen homologues. Structure and magnetic properties of the tetranuclear complex [Cu2(L2)2]2 [H2L2 = phenyl-N,N ′-bis(salicylidene)methanediamine] †. J Chem Soc, Dalton Trans 3467–3472. https://doi.org/10.1039/b003825n10.1039/b003825n ↗

15. Rigamonti L, Zardi P, Carlino S et al (2020) Selective formation, reactivity, redox and magnetic properties of MnIII and FeIII dinuclear complexes with shortened salen-type Schiff base ligands. IJMS 21:7882. https://doi.org/10.3390/ijms2121788210.3390/ijms21217882 ↗

16. Clarke RM, Herasymchuk K, Storr T (2017) Electronic structure elucidation in oxidized metal–salen complexes. Coord Chem Rev 352:67–82. https://doi.org/10.1016/j.ccr.2017.08.01910.1016/j.ccr.2017.08.019 ↗

17. Erxleben A (2018) Transition metal salen complexes in bioinorganic and medicinal chemistry. Inorg Chim Acta 472:40–57. https://doi.org/10.1016/j.ica.2017.06.06010.1016/j.ica.2017.06.060 ↗

18. Hobday MD, Smith TD (1973) N, N’-Ethylenebis(salicylideneiminato) transition metal ion chelates. Coord Chem Rev 9:311–337. https://doi.org/10.1016/S0010-8545(00)82081-010.1016/S0010-8545(00)82081-010.1016/S0010-8545(00)82081-010.1016/S0010-8545(00)82081-0 ↗

19. Nabeshima T, Yamamura M (2013) Cooperative formation and functions of multimetal supramolecular systems. Pure Appl Chem 85:763–776. https://doi.org/10.1351/PAC-CON-12-08-0210.1351/PAC-CON-12-08-02 ↗

20. Weber B, Jäger E (2009) Structure and magnetic properties of iron(II/III) complexes with N 2 O 2 2– coordinating Schiff base like ligands. Eur J Inorg Chem 2009:465–477. https://doi.org/10.1002/ejic.20080089110.1002/ejic.200800891 ↗

21. Bennani YL, Hanessian S (1997) trans -1,2-Diaminocyclohexane derivatives as chiral reagents, scaffolds, and ligands for catalysis: applications in asymmetric synthesis and molecular recognition. Chem Rev 97:3161–3196. https://doi.org/10.1021/cr940757710.1021/cr9407577 ↗

22. Kleij AW (2009) Nonsymmetrical salen ligands and their complexes: synthesis and applications. Eur J Inorg Chem 2009:193–205. https://doi.org/10.1002/ejic.20080093610.1002/ejic.200800936 ↗

23. Huber A, Müller L, Elias H et al (2005) Cobalt( II ) complexes with substituted salen-type ligands and their dioxygen affinity in N, N -dimethylformamide at various temperatures. Eur J Inorg Chem 2005:1459–1467. https://doi.org/10.1002/ejic.20040088810.1002/ejic.200400888 ↗

24. Mazzoni R, Roncaglia F, Rigamonti L (2021) When the metal makes the difference: template syntheses of tridentate and tetradentate salen-type Schiff base ligands and related complexes. Crystals 11:483. https://doi.org/10.3390/cryst1105048310.3390/cryst11050483 ↗

25. Akine S, Sunaga S, Taniguchi T et al (2007) Core/shell oligometallic template synthesis of macrocyclic hexaoxime. Inorg Chem 46:2959–2961. https://doi.org/10.1021/ic062327s10.1021/ic062327s ↗

26. Pessoa JC, Correia I (2019) Salan vs. salen metal complexes in catalysis and medicinal applications: virtues and pitfalls. Coord Chem Rev 388:227–247. https://doi.org/10.1016/j.ccr.2019.02.03510.1016/j.ccr.2019.02.035 ↗

27. Specklin D, Fliedel C, Hild F et al (2017) Mononuclear salen-gallium complexes for iso-selective ring-opening polymerization (ROP) of rac-lactide. Dalton Trans 46:12824–12834. https://doi.org/10.1039/C7DT02730C10.1039/C7DT02730C ↗

28. Baleizão C, Garcia H (2006) Chiral salen complexes: an overview to recoverable and reusable homogeneous and heterogeneous catalysts. Chem Rev 106:3987–4043. https://doi.org/10.1021/cr050973n10.1021/cr050973n ↗

29. Matsumoto K, Saito B, Katsuki T (2007) Asymmetric catalysis of metal complexes with non-planar ONNO ligands: salen, salalen and salan. Chem Commun 3619. https://doi.org/10.1039/b701431g10.1039/b701431g ↗

30. Libíková H, Pogády J, Wiedermann V, Breier S (1975) Search for herpetic antibodies in the cerebrospinal fluid in senile dementia and mental retardation. Acta Virol 19:493–495

31. Nelson SG, Peelen TJ, Wan Z (1999) Mechanistic alternatives in Lewis acid-catalyzed acyl halide aldehyde cyclocondensations. Tetrahedron Lett 40:6541–6543. https://doi.org/10.1016/S0040-4039(99)01309-X10.1016/S0040-4039(99)01309-X ↗

32. Osamura Y, Terada K, Kobayashi Y et al (1999) A molecular orbital study of the mechanism of chlorination reaction of benzene catalyzed by Lewis acid. J Mol Struct (Thoechem) 461–462:399–416. https://doi.org/10.1016/S0166-1280(98)00452-710.1016/S0166-1280(98)00452-7 ↗

33. Santelli M, Pons J-M (1996) Lewis acids and selectivity in organic synthesis. CRC Press, Boca Raton https://doi.org/10.5860/choice.34-093610.5860/choice.34-0936 ↗

34. Yoon TP, Dong VM, MacMillan DWC (1999) Development of a new Lewis acid-catalyzed Claisen rearrangement. J Am Chem Soc 121:9726–9727. https://doi.org/10.1021/ja991988410.1021/ja9919884 ↗

35. Dalton CT, Ryan KM, Wall VM et al (1998) Recent progress towards the understanding of metal–salen catalysed asymmetric alkene epoxidation. Top Catal 5:75–91. https://doi.org/10.1023/A:101910200349410.1023/A:1019102003494 ↗

36. Venkataramanan NS, Kuppuraj G, Rajagopal S (2005) Metal–salen complexes as efficient catalysts for the oxygenation of heteroatom containing organic compounds—synthetic and mechanistic aspects. Coord Chem Rev 249:1249–1268. https://doi.org/10.1016/j.ccr.2005.01.02310.1016/j.ccr.2005.01.023 ↗

37. Lidskog A, Li Y, Wärnmark K (2020) Asymmetric ring-opening of epoxides catalyzed by metal–salen complexes. Catalysts 10:705. https://doi.org/10.3390/catal1006070510.3390/catal10060705 ↗

38. Kokubo C, Katsuki T (1996) Highly enantioselective catalytic oxidation of alkyl aryl sulfides using Mn-salen catalyst. Tetrahedron 52:13895–13900. https://doi.org/10.1016/0040-4020(96)00851-410.1016/0040-4020(96)00851-4 ↗

39. Ready JM, Jacobsen EN (2001) Highly active oligomeric (salen)Co catalysts for asymmetric epoxide ring-opening reactions. J Am Chem Soc 123:2687–2688. https://doi.org/10.1021/ja005867b10.1021/ja005867b ↗

40. Shimazaki Y (2013) Oxidation Chemistry of Metal(II) Salen-type complexes. In: Khalid M (ed) Electrochemistry. InTech https://doi.org/10.5772/4837210.5772/48372 ↗

41. Cozzi PG (2004) Metal-Salen Schiff base complexes in catalysis: practical aspects. Chem Soc Rev 33:410–421. https://doi.org/10.1039/B307853C10.1039/B307853C ↗

42. Wezenberg SJ, Kleij AW (2008) Material applications for salen frameworks. Angew Chem Int Ed 47:2354–2364. https://doi.org/10.1002/anie.20070246810.1002/anie.200702468 ↗

43. Jacobsen EN, Zhang W, Muci AR et al (1991) Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane. J Am Chem Soc 113:7063–7064. https://doi.org/10.1021/ja00018a06810.1021/ja00018a068 ↗

44. Räisänen MT, Korpi H, Sundberg MR et al (2013) Synthesis and characterization of binuclear Co(II) complexes with bis(salen-type) ligands. Inorg Chim Acta 394:203–209. https://doi.org/10.1016/j.ica.2012.08.00710.1016/j.ica.2012.08.007 ↗

45. Matsunaga S, Shibasaki M (2014) Recent advances in cooperative bimetallic asymmetric catalysis: dinuclear Schiff base complexes. Chem Commun 50:1044–1057. https://doi.org/10.1039/C3CC47587E10.1039/C3CC47587E ↗

46. Kobayashi S, Sugiura M, Kitagawa H, Lam WW-L (2002) Rare-earth metal triflates in organic synthesis. Chem Rev 102:2227–2302. https://doi.org/10.1021/cr010289i10.1021/cr010289i ↗

47. Finelli A, Abram S-L, Hérault N et al (2020) Bimetallic salen-based compounds and their potential applications. Cryst Growth Des 20:4945–4958. https://doi.org/10.1021/acs.cgd.9b0161010.1021/acs.cgd.9b01610 ↗

48. Leoni L, Dalla Cort A (2018) The supramolecular attitude of metal–salophen and metal–salen complexes. Inorganics 6:42. https://doi.org/10.3390/inorganics602004210.3390/inorganics6020042 ↗

49. Whiteoak CJ, Salassa G, Kleij AW (2012) Recent advances with π-conjugated salen systems. Chem Soc Rev 41:622–631. https://doi.org/10.1039/C1CS15170C10.1039/C1CS15170C ↗

50. Oliveri IP, Di Bella S (2023) Lewis Acidic Zinc(II) Complexes of tetradentate ligands as building blocks for responsive assembled supramolecular structures. Chemistry 5:119–137. https://doi.org/10.3390/chemistry501001010.3390/chemistry5010010 ↗

51. Asatkar AK, Senanayak SP, Bedi A et al (2014) Zn( ii ) and Cu( ii ) complexes of a new thiophene-based salphen-type ligand: solution-processable high-performance field-effect transistor materials. Chem Commun 50:7036–7039. https://doi.org/10.1039/C4CC01360C10.1039/C4CC01360C ↗

52. Escudero-Adán EC, Belmonte MM, Martin E et al (2011) A short desymmetrization protocol for the coordination environment in bis-salphen scaffolds. J Org Chem 76:5404–5412. https://doi.org/10.1021/jo200806510.1021/jo2008065 ↗

53. Pietrangelo A, Sih BC, Boden BN et al (2008) Nonlinear optical properties of Schiff-base-containing conductive polymer films electro-deposited in microgravity. Adv Mater 20:2280–2284. https://doi.org/10.1002/adma.20070258210.1002/adma.200702582 ↗

54. Akine S, Taniguchi T, Nabeshima T (2001) Synthesis and crystal structure of a novel triangular macrocyclic molecule, tris(H 2 saloph), † †H2saloph=N, N′-disalicylidene-o-phenylenediamine. and its water complex. Tetrahedron Lett 42:8861–8864. https://doi.org/10.1016/S0040-4039(01)01943-810.1016/S0040-4039(01)01943-8 ↗

55. Frischmann PD, Jiang J, Hui JK-H et al (2008) Reversible−irreversible approach to Schiff base macrocycles: access to isomeric macrocycles with multiple salphen pockets. Org Lett 10:1255–1258. https://doi.org/10.1021/ol800131710.1021/ol8001317 ↗

56. Jiang J, MacLachlan MJ (2010) Unsymmetrical triangular Schiff base macrocycles with cone conformations. Org Lett 12:1020–1023. https://doi.org/10.1021/ol100028s10.1021/ol100028s ↗

57. Hui JK-H, MacLachlan MJ (2006) [6 + 6] Schiff-base macrocycles with 12 imines: giant analogues of cyclohexane. Chem Commun 2480. https://doi.org/10.1039/b603985e10.1039/b603985e ↗

58. Gerloch M, Lewis J, Mabbs FE, Richards A (1968) The preparation and magnetic properties of some Schiff base–iron( III ) halide complexes. J Chem Soc A, 112–116. https://doi.org/10.1039/J1968000011210.1039/J19680000112 ↗

59. Castilla AM, Curreli S, Escudero-Adán EC et al (2009) Modular synthesis of heterobimetallic salen structures using metal templation. Org Lett 11:5218–5221. https://doi.org/10.1021/ol902149p10.1021/ol902149p ↗

60. Wezenberg SJ, Anselmo D, Escudero-Adán EC et al (2010) Dimetallic activation of dihydrogen phosphate by Zn(salphen) chromophores. Eur J Inorg Chem 2010:4611–4616. https://doi.org/10.1002/ejic.20100045510.1002/ejic.201000455 ↗

61. Decortes A, Kleij AW (2011) Ambient fixation of carbon dioxide using a Zn II salphen catalyst. ChemCatChem 3:831–834. https://doi.org/10.1002/cctc.20110003110.1002/cctc.201100031 ↗

62. Kresge CT, Leonowicz ME, Roth WJ et al (1992) Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism. Nature 359:710–712. https://doi.org/10.1038/359710a010.1038/359710a0 ↗

63. Slowing II, Vivero-Escoto JL, Trewyn BG, Lin VS-Y (2010) Mesoporous silica nanoparticles: structural design and applications. J Mater Chem 20:7924. https://doi.org/10.1039/c0jm00554a10.1039/c0jm00554a ↗

64. ALOthman ZA (2012) A Review: Fundamental Aspects of Silicate Mesoporous Materials. Materials (Basel) 5:2874–2902. https://doi.org/10.3390/ma512287410.3390/ma5122874 ↗

65. Beck JS, Vartuli JC, Roth WJ et al (1992) A new family of mesoporous molecular sieves prepared with liquid crystal templates. J Am Chem Soc 114:10834–10843. https://doi.org/10.1021/ja00053a02010.1021/ja00053a020 ↗

66. Yu C, Yu Y, Zhao D (2000) Highly ordered large caged cubic mesoporous silica structures templated by triblock PEO–PBO–PEO copolymer. Chem Commun 575–576. https://doi.org/10.1039/b000603n10.1039/b000603n ↗

67. Bagshaw SA, Prouzet E, Pinnavaia TJ (1995) Templating of mesoporous molecular sieves by nonionic polyethylene oxide surfactants. Science 269:1242–1244. https://doi.org/10.1126/science.269.5228.124210.1126/science.269.5228.1242 ↗

68. Che S, Garcia-Bennett AE, Yokoi T et al (2003) A novel anionic surfactant templating route for synthesizing mesoporous silica with unique structure. Nature Mater 2:801–805. https://doi.org/10.1038/nmat102210.1038/nmat1022 ↗

69. Chew T-L, Ahmad AL, Bhatia S (2010) Ordered mesoporous silica (OMS) as an adsorbent and membrane for separation of carbon dioxide (CO2). Adv Coll Interface Sci 153:43–57. https://doi.org/10.1016/j.cis.2009.12.00110.1016/j.cis.2009.12.001 ↗

70. Nnamdi Chibuike Iheaturu (2014) Synthesis, preparation and characterization of nanoporous core-shell-clay epoxy composites.https://doi.org/10.13140/RG.2.2.23461.9136110.13140/RG.2.2.23461.91361 ↗

71. Yamaguchi T, Yoshida K, Ito K et al (2011) Thermal behavior, structure, and dynamics of low temperature water confined in mesoporous materials MCM-41. Bunseki Kagaku 60:115–130. https://doi.org/10.2116/bunsekikagaku.60.11510.2116/bunsekikagaku.60.115 ↗

72. Janus R, Wądrzyk M, Lewandowski M et al (2020) Understanding porous structure of SBA-15 upon pseudomorphic transformation into MCM-41: Non-direct investigation by carbon replication. J Ind Eng Chem 92:131–144. https://doi.org/10.1016/j.jiec.2020.08.03210.1016/j.jiec.2020.08.032 ↗

73. Andas J, Ekhbal SH, Ali TH (2021) MCM-41 modified heterogeneous catalysts from rice husk for selective oxidation of styrene into benzaldehyde. Environ Technol Innov 21:101308. https://doi.org/10.1016/j.eti.2020.10130810.1016/j.eti.2020.101308 ↗

74. Bhattacharyya S, Lelong G, Saboungi M-L (2006) Recent progress in the synthesis and selected applications of MCM-41: a short review. J Exp Nanosci 1:375–395. https://doi.org/10.1080/1745808060081275710.1080/17458080600812757 ↗

75. García-Martínez J (2015) Mesostructured zeolites: bridging the gap between zeolites and MCM-41. ChemViews. https://doi.org/10.1002/chemv.20150005610.1002/chemv.201500056 ↗

76. Yamada SA, Hung ST, Thompson WH, Fayer MD (2020) Effects of pore size on water dynamics in mesoporous silica. J Chem Phys 152:154704. https://doi.org/10.1063/1.514532610.1063/1.5145326 ↗

77. Laskowski Ł, Laskowska M, Vila N et al (2019) Mesoporous silica-based materials for electronics-oriented applications. Molecules 24:2395. https://doi.org/10.3390/molecules2413239510.3390/molecules24132395 ↗

78. Dhaneswara D, Sofyan N (2016) Effect of different pluronic P123 triblock copolymer surfactant concentrations on SBA-15 pore formation. IJTech 7:1009. https://doi.org/10.14716/ijtech.v7i6.341210.14716/ijtech.v7i6.3412 ↗

79. Da Silveira T, Awano CM, Donatti DA et al (2014) About the thermal stability and pore elimination in the ordered hexagonal mesoporous silica SBA-15. Microporous Mesoporous Mater 190:227–233. https://doi.org/10.1016/j.micromeso.2014.02.02310.1016/j.micromeso.2014.02.023 ↗

80. Fedyna M, Śliwa M, Jaroszewska K et al (2020) Procedure for the synthesis of AlSBA-15 with high aluminium content: characterization and catalytic activity. Microporous Mesoporous Mater 292:109701. https://doi.org/10.1016/j.micromeso.2019.10970110.1016/j.micromeso.2019.109701 ↗

81. Mahato BN, Krithiga T (2022) Recent developments in metal-doped SBA-15 catalysts for heterogeneous catalysis and sustainable chemistry. Can J Chem 100:9–17. https://doi.org/10.1139/cjc-2021-020110.1139/cjc-2021-0201 ↗

82. An K, Somorjai GA (2015) Nanocatalysis I: synthesis of metal and bimetallic nanoparticles and porous oxides and their catalytic reaction studies. Catal Lett 145:233–248. https://doi.org/10.1007/s10562-014-1399-x10.1007/s10562-014-1399-x ↗

83. Gkiliopoulos D, Tsamesidis I, Theocharidou A et al (2022) SBA-15 mesoporous silica as delivery vehicle for rhBMP-2 bone morphogenic protein for dental applications. Nanomaterials 12:822. https://doi.org/10.3390/nano1205082210.3390/nano12050822 ↗

84. Larki A, Saghanezhad SJ, Ghomi M (2021) Recent advances of functionalized SBA-15 in the separation/preconcentration of various analytes: a review. Microchem J 169:106601. https://doi.org/10.1016/j.microc.2021.10660110.1016/j.microc.2021.106601 ↗

85. Shakeri M, Khatami Shal Z, Van Der Voort P (2021) An overview of the challenges and progress of synthesis, characterization and applications of plugged SBA-15 materials for heterogeneous catalysis. Materials 14:5082. https://doi.org/10.3390/ma1417508210.3390/ma14175082 ↗

86. Wang J, Wang G, Zhang Z et al (2021) Effects of mesoporous silica particle size and pore structure on the performance of polymer-mesoporous silica mixed matrix membranes. RSC Adv 11:36577–36586. https://doi.org/10.1039/D1RA05125C10.1039/D1RA05125C ↗

87. Yates TJV, Thomas JM, Fernandez J-J et al (2006) Three-dimensional real-space crystallography of MCM-48 mesoporous silica revealed by scanning transmission electron tomography. Chem Phys Lett 418:540–543. https://doi.org/10.1016/j.cplett.2005.11.03110.1016/j.cplett.2005.11.031 ↗

88. Kumar D, Schumacher K, Von Hohenesche CD et al (2001) MCM-41, MCM-48 and related mesoporous adsorbents: their synthesis and characterisation. Colloids Surf A: Physicochem Eng Asp 187–188:109–116. https://doi.org/10.1016/S0927-7757(01)00638-010.1016/S0927-7757(01)00638-0 ↗

89. Taralkar US, Kasture MW, Joshi PN (2008) Influence of synthesis conditions on structural properties of MCM-48. J Phys Chem Solids 69:2075–2081. https://doi.org/10.1016/j.jpcs.2008.03.00410.1016/j.jpcs.2008.03.004 ↗

90. Jana S, Dutta B, Honda H, Koner S (2011) Mesoporous silica MCM-41 with rod-shaped morphology: synthesis and characterization. Appl Clay Sci 54:138–143. https://doi.org/10.1016/j.clay.2011.07.01810.1016/j.clay.2011.07.018 ↗

91. Brankovic M, Zarubica A, Andjelkovic T, Andjelkovic D (2017) Mesoporous silica (MCM-41): Synthesis/modification, characterization and removal of selected organic micro-pollutants from water. Adv techn 6:50–57. https://doi.org/10.5937/savteh1701050B10.5937/savteh1701050B ↗

92. Pratiwi FW, Kuo CW, Wu S-H, et al (2018) The bioimaging applications of mesoporous silica nanoparticles. In: The Enzymes. Elsevier, pp 123–153 https://doi.org/10.1016/bs.enz.2018.07.00610.1016/bs.enz.2018.07.006 ↗

93. Chaudhary V, Sharma S (2017) An overview of ordered mesoporous material SBA-15: synthesis, functionalization and application in oxidation reactions. J Porous Mater 24:741–749. https://doi.org/10.1007/s10934-016-0311-z10.1007/s10934-016-0311-z ↗

94. Kim T-W, Chung P-W, Lin VS-Y (2010) Facile synthesis of monodisperse spherical MCM-48 mesoporous silica nanoparticles with controlled particle size. Chem Mater 22:5093–5104. https://doi.org/10.1021/cm101734410.1021/cm1017344 ↗

95. Pantazis CC, Trikalitis PN, Pomonis PJ, Hudson MJ (2003) A method of synthesis of silicious inorganic ordered materials (MCM-41–SBA-1) employing polyacrylic acid–CnTAB–TEOS nanoassemblies. Microporous Mesoporous Mater 66:37–51. https://doi.org/10.1016/j.micromeso.2003.08.01710.1016/j.micromeso.2003.08.017 ↗

96. Florensa M, Llenas M, Medina-Gutiérrez E et al (2022) Key parameters for the rational design, synthesis, and functionalization of biocompatible mesoporous silica nanoparticles. Pharmaceutics 14:2703. https://doi.org/10.3390/pharmaceutics1412270310.3390/pharmaceutics14122703 ↗

97. Miceli M, Frontera P, Macario A, Malara A (2021) Recovery/reuse of heterogeneous supported spent catalysts. Catalysts 11:591. https://doi.org/10.3390/catal1105059110.3390/catal11050591 ↗

98. Ganesan V, Yoon S (2020) Direct heterogenization of salphen coordination complexes to porous organic polymers: catalysts for ring-expansion carbonylation of epoxides. Inorg Chem 59:2881–2889. https://doi.org/10.1021/acs.inorgchem.9b0324710.1021/acs.inorgchem.9b03247 ↗

99. Yilmaz F, Karaağaç Y, Kani̇ İ (2017) Heterogenization of homogeneous perfluorothiophene Rh(I) complex and examination of hydrogenation activity in scCO2 media. Anadolu University Journal of Science and Technology A-Applied Sciences and Engineering 1–1. https://doi.org/10.18038/aubtda.33115910.18038/aubtda.331159 ↗

100. Lantos J, Kumar N, Saha B (2024) A comprehensive review of fine chemical production using metal-modified and acidic microporous and mesoporous catalytic materials. Catalysts 14:317. https://doi.org/10.3390/catal1405031710.3390/catal14050317 ↗