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1420-304929122024Jun18Molecules (Basel, Switzerland)MoleculesThe Grafting of Hydroxyaromatic Organics within Layered Perovskites via a Microwave-Assisted Method.288810.3390/molecules29122888A new series of inorganic-organic hybrid perovskite materials were prepared by microwave-assisted grafting reactions. Simple carboxylic acids, acetic acid, and propionic acid, as well as hydroxyaromatic carboxylic acids, 3,5-dihydroxy benzoic acid (DBA), 5-hydroxyisophthalic acid (HPA), 4-hydroxybenzoic acid (HBA), and 4-hydroxy-4-biphenyl carboxylic acid (HBCA), were reacted with the Dion-Jacobson double-layered perovskite, HLaNb2O7, and its alcoxy derivatives. Grafting was found to not occur with simple carboxylic acids, while those molecules with hydroxyls were all attached to the perovskite interlayers. Reactivity of the hydroxyaromatic carboxylic acids varied with the different layered perovskite hosts where reactions with HLaNb2O7 did not occur, and those with n-propoxy-LaNb2O7 were limited; the greatest extent of reactivity was seen with n-decoxy-LaNb2O7. This is attributed to the larger interlayer spacing available for the insertion of the various hydroxyaromatic carboxylic acid compounds. The loading exhibited by the grafting species was less than that seen with well-known long-chain alkoxy grafting groups. It is expected that the width of the molecules contributes to this where, due to the benzyl groups, the interlayer volume of the grafted moieties occupies a larger horizontal fraction, therefore minimizing the loading to the below half. X-ray powder diffraction and transmission electron microscopy studies found that grafting of the n-decoxy-LaNb2O7 intermediates with the series of hydroxyaromatics resulted in a reduction in crystallinity along with a disruption of the layer structure. Raman data on the series show little variation in local structure except for HBCA, where there appears to be a lengthening of the Nb-O apical linkage and a possible reduction in the distortion of inner-layer NbO6 octahedra. The optical properties of the hydroxyaromatic carboxylic acid grafted perovskites were also investigated using diffuse-reflectance UV-Vis spectroscopy. The band gaps of DBA, HPA, and HBA were found to be similar to the parent (Eg ≈ 3.4 eV), while the HBCA was significantly less by ca. 0.6 eV. This difference is attributed to electron withdrawal from the perovskite block to the HBCA ligand, leading to a lower band gap for the HBCA compound. The methods described herein allow for the formation of a new series of inorganic-organic hybrid materials where the products are of interest as precursors to more complex architectures as well as models for band gap modification of metal oxide photocatalysts.PoduvalAnamikaA0000-0002-1318-7164Department of Chemistry and Advanced Materials Research Institute, University of New Orleans, New Orleans, LA 70148, USA.JonesKirsten DKDDepartment of Chemistry and Advanced Materials Research Institute, University of New Orleans, New Orleans, LA 70148, USA.LeBanLevon ALA2ndDepartment of Chemistry and Advanced Materials Research Institute, University of New Orleans, New Orleans, LA 70148, USA.WileyJohn BJB0000-0002-6954-6752Department of Chemistry and Advanced Materials Research Institute, University of New Orleans, New Orleans, LA 70148, USA.engJournal Article20240618
SwitzerlandMolecules1009640091420-3049IMgraftinglayered perovskiteorganic–inorganic hybridtopochemistryThe authors declare no conflict of interest.20244320246720246122024627643202462764220246271202024618epublish38930953PMC1120636810.3390/molecules29122888molecules29122888Uppuluri R., Sen Gupta A., Rosas A.S., Mallouk T.E. Soft chemistry of ion-exchangeable layered metal oxides. Chem. Soc. Rev. 2018;47:2401–2430. doi: 10.1039/C7CS00290D.10.1039/C7CS00290D29479626Dion M., Ganne M., Tournoux M. The new phase families mim2(ii)nb3010 with perovskite sheets. Mater. Res. Bull. 1981;16:1429–1435. doi: 10.1016/0025-5408(81)90063-5.10.1016/0025-5408(81)90063-5Jacobson A.J., Johnson J.W., Lewandowski J.T. Interlayer chemistry between thick transition-metal oxide layers—Synthesis and intercalation reactions of K[Ca2Nan-3NbnO3n+1] (3 .ltoreq. n .ltoreq. 7) Inorg. Chem. 1985;24:3727–3729. doi: 10.1021/ic00217a006.10.1021/ic00217a006Chen D.L., Sugahara Y. Tungstate-based inorganic-organic hybrid nanobelts/nanotubes with lamellar mesostructures: Synthesis, characterization, and formation mechanism. Chem. Mater. 2007;19:1808–1815. doi: 10.1021/cm062039u.10.1021/cm062039uKobayashi Y., Tian M., Eguchi M., Mallouk T.E. Ion-Exchangeable, Electronically Conducting Layered Perovskite Oxyfluorides. J. Am. Chem. Soc. 2009;131:9849–9855. doi: 10.1021/ja9040829.10.1021/ja904082919548670Gomez-Romero P., Palacin M.R., Casan N., Fuertes A. Synthesis of a reduced niobium blue with a layered perovskite structure. Solid State Ion. 1993;63–65:424–428. doi: 10.1016/0167-2738(93)90139-T.10.1016/0167-2738(93)90139-TLichtenberg F., Herrnberger A., Wiedenmann K. Synthesis, structural, magnetic and transport properties of layered perovskite-related titanates, niobates and tantalates of the type AnBnO3n+2, A′Ak−1BkO3k+1 and AmBm−1O3m. Prog. Solid State Chem. 2008;36:253–387. doi: 10.1016/j.progsolidstchem.2008.10.001.10.1016/j.progsolidstchem.2008.10.001Kato M., Imai Y., Kajita T., Takarabe Y., Minakawa T., Nemoto K., Tezuka H., Noji T., Koike Y. Synthesis of oxide superconductors by soft-chemical techniques. Mater. Sci. Eng. B Adv. Funct. Solid-State Mater. 2008;148:53–57. doi: 10.1016/j.mseb.2007.09.031.10.1016/j.mseb.2007.09.031Kong J., Nayak S.K., Liu J., Alpay S.P., Pramanick A. Local atomic structure distortions in the Dion-Jacobson ferroelectric CsBiNb2O7. Phys. Rev. B. 2022;106:6. doi: 10.1103/PhysRevB.106.024103.10.1103/PhysRevB.106.024103Rodionov I.A., Zvereva I.A. Photocatalytic activity of layered perovskite-like oxides in practically valuable chemical reactions. Russ. Chem. Rev. 2016;85:248–279. doi: 10.1070/RCR4547.10.1070/RCR4547Ranmohotti K.G.S., Josepha E., Choi J., Zhang J.X., Wiley J.B. Topochemical Manipulation of Perovskites: Low-Temperature Reaction Strategies for Directing Structure and Properties. Adv. Mater. 2011;23:442–460. doi: 10.1002/adma.201002274.10.1002/adma.20100227421254250Kikkawa S. Kanamaru, Fumikazu, Koizumi, Mitsue, Synthesis and some properties of iron oxide methoxide. A new layered compound. Inorg. Chem. Commun. 1976;15:2195–2197. doi: 10.1021/ic50163a039.10.1021/ic50163a039Sugahara Y. Chemical processes employing inorganic layered compounds for inorganic and inorganic-organic hybrid materials. J. Ceram. Soc. Jpn. 2014;122:523–529. doi: 10.2109/jcersj2.122.523.10.2109/jcersj2.122.523Shelyapina M.G., Silyukov O.I., Lushpinskaia I.P., Kurnosenko S.A., Mazur A.S., Shenderovich I.G., Zvereva I.A. NMR Study of Intercalates and Grafted Organic Derivatives of H2La2Ti3O10. Molecules. 2020;25:5229. doi: 10.3390/molecules25225229.10.3390/molecules25225229PMC769660333182612Akbarian-Tefaghi S., Veiga E.T., Amand G., Wiley J.B. Rapid Topochemical Modification of Layered Perovskites via Microwave Reactions. Inorg. Chem. 2016;55:1604–1612. doi: 10.1021/acs.inorgchem.5b02514.10.1021/acs.inorgchem.5b0251426835716Sugimoto W., Shirata M., Sugahara Y., Kuroda K. New conversion reaction of an Aurivillius phase into the protonated form of the layered perovskite by the selective leaching of the bismuth oxide sheet. J. Am. Chem. Soc. 1999;121:11601–11602. doi: 10.1021/ja9927265.10.1021/ja9927265Yoshioka S., Takeda Y., Uchimaru Y., Sugahara Y. Hydrosilylation in the 2D interlayer space between inorganic layers: Reaction between immobilized C=C groups on the interlayer surface of layered perovskite HLaNb2O7 center dot xH2O and chlorohydrosilanes. J. Organomet. Chem. 2003;686:145–150. doi: 10.1016/S0022-328X(03)00618-1.10.1016/S0022-328X(03)00618-1Takeda Y., Momma T., Osaka T., Kuroda K., Sugahara Y. Organic derivatives of the layered perovskite HLaNb2O7 center dot xH(2)O with polyether chains on the interlayer surface: Characterization, intercalation of LiClO4, and ionic conductivity. J. Mater. Chem. 2008;18:3581–3587. doi: 10.1039/b802003e.10.1039/b802003eShimada A., Yoneyama Y., Tahara S., Mutin R.H., Sugahara Y. Interlayer surface modification of the protonated ion-exchangeable layered perovskite HLaNb2O7 center dot xH2O with organophosphonic acids. Chem. Mater. 2009;21:4155–4162. doi: 10.1021/cm900228c.10.1021/cm900228cTahara S., Sugahara Y. Interlayer surface modification of the protonated triple-layered perovskite HCa2Nb3O10 center dot xH2O with n-alcohols. Langmuir. 2003;19:9473–9478. doi: 10.1021/la0343876.10.1021/la0343876Giguere R.J., Bray T.L., Duncan S.M., Majetich G. Application of Commercial Microwave Ovens to Organic Synthesis. Tetrahedron Lett. 1986;27:4945. doi: 10.1016/S0040-4039(00)85103-5.10.1016/S0040-4039(00)85103-5Hsin Y.L., Lin C.F., Liang Y.C., Hwang K.C., Horng J.C., Ho J.A.A., Lin C.C., Hwu J.R. Microwave arcing induced formation and growth mechanisms of core/shell metal/carbon nanoparticles in organic solutions. Adv. Funct. Mater. 2008;18:2048–2056. doi: 10.1002/adfm.200701407.10.1002/adfm.200701407Wang Y., Nikolopoulou M., Delahaye E., Leuvrey C., Leroux F., Rabu P., Rogez G. Microwave-assisted functionalization of the Aurivillius phase Bi2SrTa2O9: Diol grafting and amine insertion vs. alcohol grafting. Chem. Sci. 2018;9:7104–7114. doi: 10.1039/C8SC01754A.10.1039/C8SC01754APMC613744630310631Boykin J.R., Smith L.J. Rapid Microwave-Assisted Grafting of Layered Perovskites with n-Alcohols. Inorg. Chem. 2015;54:4177–4179. doi: 10.1021/ic503001w.10.1021/ic503001w25906189Wang Y.H., Delahaye E., Leuvrey C., Leroux F., Rabu P., Rogez G. Post-Synthesis Modification of the Aurivillius Phase Bi2SrTa2O9 via In Situ Microwave-Assisted “Click Reaction”. Inorg. Chem. 2016;55:9790–9797. doi: 10.1021/acs.inorgchem.6b01600.10.1021/acs.inorgchem.6b0160027618400Wang Y.H., Delahaye E., Leuvrey C., Leroux F., Rabu P., Rogez G. Efficient Microwave-Assisted Functionalization of the Aurivillius-Phase Bi2SrTa2O9. Inorg. Chem. 2016;55:4039–4046. doi: 10.1021/acs.inorgchem.6b00338.10.1021/acs.inorgchem.6b0033827042754Wang Y., Leuvrey C., Delahaye E., Leroux F., Rabu P., Taviot-Guého C., Rogez G. Tuning the organization of the interlayer organic moiety in a hybrid layered perovskite. J. Solid State Chem. 2019;269:532–539. doi: 10.1016/j.jssc.2018.10.034.10.1016/j.jssc.2018.10.034Akbarian-Tefaghi S., Rostamzadeh T., Brown T.T., Davis-Wheeler C., Wiley J.B. Rapid Exfoliation and Surface Tailoring of Perovskite Nanosheets via Microwave-Assisted Reactions. ChemNanoMat. 2017;3:538–550. doi: 10.1002/cnma.201700124.10.1002/cnma.201700124Takeda Y., Suzuki H., Notsu K., Sugimoto W., Sugahara Y. Preparation of a novel organic derivative of the layered perovskite bearing HLaNb2O7 center dot nH2O interlayer surface trifluoroacetate groups. Mater. Res. Bull. 2006;41:834–841. doi: 10.1016/j.materresbull.2005.10.004.10.1016/j.materresbull.2005.10.004Tahara S., Ichikawa T., Kajiwara G., Sugahara Y. Reactivity of the Ruddlesden-Popper phase H2La2Ti3O10 with organic compounds: Intercalation and grafting reactions. Chem. Mater. 2007;19:2352–2358. doi: 10.1021/cm0623662.10.1021/cm0623662Shimojima A., Sugahara Y., Kuroda K. Inorganic-organic layered materials derived via the hydrolysis and polycondensation of trialkoxy(alkyl)silanes. Bull. Chem. Soc. Jpn. 1997;70:2847–2853. doi: 10.1246/bcsj.70.2847.10.1246/bcsj.70.2847Takahashi S., Nakato T., Hayashi S., Sugahara Y., Kuroda K. Formation of a methoxy-modified interlayer surface via the reaction between methanol and layered perovskite hlanb2o7-center-dot-xh2o. Inorg. Chem. 1995;34:5065–5069. doi: 10.1021/ic00124a023.10.1021/ic00124a023Suzuki H., Notsu K., Takeda Y., Sugimoto W., Sugahara Y. Reactions of alkoxyl derivatives of a layered perovskite with alcohols: Substitution reactions on the interlayer surface of a layered perovskite. Chem. Mater. 2003;15:636–641. doi: 10.1021/cm0200902.10.1021/cm0200902Jehng J.M., Wachs I.E. Structural chemistry and raman-spectra of niobium oxides. Chem. Mater. 1991;3:100–107. doi: 10.1021/cm00013a025.10.1021/cm00013a025Byeon S.H., Nam H.J. Neutron diffraction and FT-Raman study of ion-exchangeable layered titanates and niobates. Chem. Mater. 2000;12:1771–1778. doi: 10.1021/cm9906506.10.1021/cm9906506Kim H.J., Byeon S.H., Yun H. Raman spectra of the solid-solution between Rb2La2Ti3O10 and RbCa2Nb3O10. Bull. Korean Chem. Soc. 2001;22:298–302.Hase I., Nishihara Y. Electronic structure of the superconducting layered perovskite niobate. Phys. Rev. B. 1998;58:R1707–R1709. doi: 10.1103/PhysRevB.58.R1707.10.1103/PhysRevB.58.R1707Xu N., Takei T., Miura A., Kumada N. Photocatalytic Activities of Layered Niobate Perovskite (A’An−1NbnO3n+1, A: Ca, La) with Substitution of Ti and W for Nb. J. Ion Exch. 2014;25:242–247. doi: 10.5182/jaie.25.242.10.5182/jaie.25.242Maeda K., Mallouk T.E. Comparison of two- and three-layer restacked Dion-Jacobson phase niobate nanosheets as catalysts for photochemical hydrogen evolution. J. Mater. Chem. 2009;19:4813–4818. doi: 10.1039/b903692j.10.1039/b903692jPalacin M.R., Lira M., Garcia J.L., Caldes M.T., Casan-Pastor N., Fuertes A., Gomez-Romero P. Synthesis deintercalation and transport properties of a mixed-valence derivative of the layered oxide HLaNb2O7. Mater. Res. Bull. 1996;31:217–225. doi: 10.1016/0025-5408(95)00179-4.10.1016/0025-5408(95)00179-4Akbarian-Tefaghi S. Ph.D. Dissertation. University of New Orleans; New Orleans, LA, USA: 2017. Microwave-Assisted Topochemical Manipulation of Layered Oxide Perovskites: From Inorganic Layered Oxides to Inorganic-Organic Hybrid Perovskites and Functionalized Metal-Oxide Nanosheets.Nozaki R., Kondo J.N., Hirose C., Domen K., Wada A., Morioka Y. Vibrational study of layered perovskites M2La2Ti3O10 (M = Li, Na, K, Rb): Raman spectra and normal mode analysis. J. Phys. Chem. B. 2001;105:7950–7953. doi: 10.1021/jp010839g.10.1021/jp010839gLaugier J., Bochu B. ChekCell; Domaine Universitaire: Saint Martin d’Hères, France. [(accessed on 11 June 2024)]. Available online: https://www.ccp14.ac.uk/ccp/web-mirrors/lmgp-laugier-bochu/Bhadra B.N., Ahmed I., Lee H.J., Jhung S.H. Metal-organic frameworks bearing free carboxylic acids: Preparation, modification, and applications. Coord. Chem. Rev. 2022;450:214237. doi: 10.1016/j.ccr.2021.214237.10.1016/j.ccr.2021.214237Bondi A. van der Waals Volumes and Radii. J. Phys. Chem. 1964;68:441–451. doi: 10.1021/j100785a001.10.1021/j100785a001Bond A.D., Davies J.E. n-Decane. Acta Crystallogr. Sect. E. 2002;58:196–197. doi: 10.1107/S1600536802001332.10.1107/S1600536802001332trying2...
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The Grafting of Hydroxyaromatic Organics within Layered Perovskites via a Microwave-Assisted Method. | LitMetric
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The Grafting of Hydroxyaromatic Organics within Layered Perovskites via a Microwave-Assisted Method.

Anamika Poduval Kirsten D Jones Levon A LeBan John B Wiley

Molecules

Department of Chemistry and Advanced Materials Research Institute, University of New Orleans, New Orleans, LA 70148, USA.

Published: June 2024

A new series of inorganic-organic hybrid perovskite materials were prepared by microwave-assisted grafting reactions. Simple carboxylic acids, acetic acid, and propionic acid, as well as hydroxyaromatic carboxylic acids, 3,5-dihydroxy benzoic acid (DBA), 5-hydroxyisophthalic acid (HPA), 4-hydroxybenzoic acid (HBA), and 4-hydroxy-4-biphenyl carboxylic acid (HBCA), were reacted with the Dion-Jacobson double-layered perovskite, HLaNbO and its alcoxy derivatives. Grafting was found to not occur with simple carboxylic acids, while those molecules with hydroxyls were all attached to the perovskite interlayers. Reactivity of the hydroxyaromatic carboxylic acids varied with the different layered perovskite hosts where reactions with HLaNbO did not occur, and those with n-propoxy-LaNbO were limited; the greatest extent of reactivity was seen with n-decoxy-LaNbO. This is attributed to the larger interlayer spacing available for the insertion of the various hydroxyaromatic carboxylic acid compounds. The loading exhibited by the grafting species was less than that seen with well-known long-chain alkoxy grafting groups. It is expected that the width of the molecules contributes to this where, due to the benzyl groups, the interlayer volume of the grafted moieties occupies a larger horizontal fraction, therefore minimizing the loading to the below half. X-ray powder diffraction and transmission electron microscopy studies found that grafting of the n-decoxy-LaNbO intermediates with the series of hydroxyaromatics resulted in a reduction in crystallinity along with a disruption of the layer structure. Raman data on the series show little variation in local structure except for HBCA, where there appears to be a lengthening of the Nb-O apical linkage and a possible reduction in the distortion of inner-layer NbO octahedra. The optical properties of the hydroxyaromatic carboxylic acid grafted perovskites were also investigated using diffuse-reflectance UV-Vis spectroscopy. The band gaps of DBA, HPA, and HBA were found to be similar to the parent (E ≈ 3.4 eV), while the HBCA was significantly less by ca. 0.6 eV. This difference is attributed to electron withdrawal from the perovskite block to the HBCA ligand, leading to a lower band gap for the HBCA compound. The methods described herein allow for the formation of a new series of inorganic-organic hybrid materials where the products are of interest as precursors to more complex architectures as well as models for band gap modification of metal oxide photocatalysts.

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