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Maya chemistry of organic inorganic hybrid materials: isomerization, cyclicization and redox tuning of organic dyes attached to porous silicates

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Maya chemistry of organic inorganic hybrid materials: isomerization, cyclicization and redox tuning of organic dyes attached to porous silicates

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Domenech Carbo, A.; Valle-Algarra, FM.; Domenech Carbo, MT.; Osete Cortina, L.; Domine, ME. (2013). Maya chemistry of organic inorganic hybrid materials: isomerization, cyclicization and redox tuning of organic dyes attached to porous silicates. RSC Advances. 3:20099-20105. https://doi.org/10.1039/c3ra42890g

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Title: Maya chemistry of organic inorganic hybrid materials: isomerization, cyclicization and redox tuning of organic dyes attached to porous silicates
Author: Domenech Carbo, Antonio Valle-Algarra, Francisco M. Domenech Carbo, Mª Teresa Osete Cortina, Laura Domine, Marcelo Eduardo
UPV Unit: Universitat Politècnica de València. Departamento de Conservación y Restauración de Bienes Culturales - Departament de Conservació i Restauració de Béns Culturals
Universitat Politècnica de València. Instituto Universitario de Restauración del Patrimonio - Institut Universitari de Restauració del Patrimoni
Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química
Issued date:
Abstract:
[EN] Association of indigo and lapachol dyes to aluminosilicate clays yields polyfunctional organic – inorganic hybrid materials forming Maya Blue-like systems. Upon partial removing of clay's zeolitic water ...[+]
Subjects: Maya chemistry , Maya Blue
Copyrigths: Reserva de todos los derechos
Source:
RSC Advances. (issn: 2046-2069 ) (eissn: 2046-2069 )
DOI: 10.1039/c3ra42890g
Publisher:
Royal Society of Chemistry
Publisher version: http://www.rsc.org/journals-books-databases/about-journals/rsc-advances/?id=8317
Project ID:
info:eu-repo/grantAgreement/MINECO//CTQ2011-28079-C03-01/ES/DESARROLLO DE METODOS NANOELECTROQUIMICOS DE ANALISIS DE OBRA PICTORICA BASADOS EN LA TECNICA DE MICROSCOPIA DE FUERZA ATOMICA-VOLTAMETRIA DE NANOPARTICULAS/
info:eu-repo/grantAgreement/MINECO//CTQ2011-28079-C03-02/ES/DESARROLLO DE METODOS NANOELECTROQUIMICOS DE ANALSISIS DE OBRAS PICTORICAS BASADOS EN "ONE-TOUCH", "LAYER-BY-LAYER" VOLTAMPEROMETRIA DE MICRO%2FNANOPARTICULAS Y MICROSCOPIA ELEC/
Thanks:
Financial support is gratefully acknowledged from the MEC Projects CTQ2011-28079-CO3-01 and 02 which are also supported with ERDF funds.
Type: Artículo

References

Gómez-Romero, P., & Sanchez, C. (2005). Hybrid materials. Functional properties. From Maya Blue to 21st century materials. New J. Chem., 29(1), 57-58. doi:10.1039/b416075b

Calzaferri, G., Huber, S., Maas, H., & Minkowski, C. (2003). Host–Guest Antenna Materials. Angewandte Chemie International Edition, 42(32), 3732-3758. doi:10.1002/anie.200300570

Doménech, A., Doménech-Carbó, M. T., Sánchez del Río, M., Vázquez de Agredos Pascual, M. L., & Lima, E. (2009). Maya Blue as a nanostructured polyfunctional hybrid organic–inorganic material: the need to change paradigms. New Journal of Chemistry, 33(12), 2371. doi:10.1039/b901942a [+]
Gómez-Romero, P., & Sanchez, C. (2005). Hybrid materials. Functional properties. From Maya Blue to 21st century materials. New J. Chem., 29(1), 57-58. doi:10.1039/b416075b

Calzaferri, G., Huber, S., Maas, H., & Minkowski, C. (2003). Host–Guest Antenna Materials. Angewandte Chemie International Edition, 42(32), 3732-3758. doi:10.1002/anie.200300570

Doménech, A., Doménech-Carbó, M. T., Sánchez del Río, M., Vázquez de Agredos Pascual, M. L., & Lima, E. (2009). Maya Blue as a nanostructured polyfunctional hybrid organic–inorganic material: the need to change paradigms. New Journal of Chemistry, 33(12), 2371. doi:10.1039/b901942a

Hubbard, B., Kuang, W., Moser, A., Facey, G. A., & Detellier, C. (2003). Structural study of Maya Blue: textural, thermal and solidstate multinuclear magnetic resonance characterization of the palygorskite-indigo and sepiolite-indigo adducts. Clays and Clay Minerals, 51(3), 318-326. doi:10.1346/ccmn.2003.0510308

Fois, E., Gamba, A., & Tilocca, A. (2003). On the unusual stability of Maya blue paint: molecular dynamics simulations. Microporous and Mesoporous Materials, 57(3), 263-272. doi:10.1016/s1387-1811(02)00596-6

Sánchez del Río, M., Martinetto, P., Somogyi, A., Reyes-Valerio, C., Dooryhée, E., Peltier, N., … Dran, J.-C. (2004). Microanalysis study of archaeological mural samples containing Maya blue pigment. Spectrochimica Acta Part B: Atomic Spectroscopy, 59(10-11), 1619-1625. doi:10.1016/j.sab.2004.07.027

Giustetto, R., Llabrés i Xamena, F. X., Ricchiardi, G., Bordiga, S., Damin, A., Gobetto, R., & Chierotti, M. R. (2005). Maya Blue:  A Computational and Spectroscopic Study. The Journal of Physical Chemistry B, 109(41), 19360-19368. doi:10.1021/jp048587h

Doménech, A., Doménech-Carbó, M. T., & Vázquez de Agredos Pascual, M. L. (2006). Dehydroindigo:  A New Piece into the Maya Blue Puzzle from the Voltammetry of Microparticles Approach. The Journal of Physical Chemistry B, 110(12), 6027-6039. doi:10.1021/jp057301l

Doménech, A., Doménech-Carbó, M. T., & Vázquez de Agredos Pascual, M. L. (2007). Indigo/Dehydroindigo/Palygorskite Complex in Maya Blue:  An Electrochemical Approach. The Journal of Physical Chemistry C, 111(12), 4585-4595. doi:10.1021/jp067369g

Doménech, A., Doménech-Carbó, M. T., & de Agredos Pascual, M. L. V. (2007). Chemometric Study of Maya Blue from the Voltammetry of Microparticles Approach. Analytical Chemistry, 79(7), 2812-2821. doi:10.1021/ac0623686

DOMÉNECH, A., DOMÉNECH-CARBÓ, M. T., & VÁZQUEZ DE AGREDOS PASCUAL, M. L. (2009). CORRELATION BETWEEN SPECTRAL, SEM/EDX AND ELECTROCHEMICAL PROPERTIES OF MAYA BLUE: A CHEMOMETRIC STUDY*. Archaeometry, 51(6), 1015-1034. doi:10.1111/j.1475-4754.2009.00453.x

Doménech, A., Doménech-Carbó, M. T., & Vázquez de Agredos-Pascual, M. L. (2011). From Maya Blue to «Maya Yellow»: A Connection between Ancient Nanostructured Materials from the Voltammetry of Microparticles. Angewandte Chemie International Edition, 50(25), 5741-5744. doi:10.1002/anie.201100921

Doménech, A., Doménech-Carbó, M. T., Vidal-Lorenzo, C., & de Agredos-Pascual, M. L. V. (2011). Insights into the Maya Blue Technology: Greenish Pellets from the Ancient City of La Blanca. Angewandte Chemie International Edition, 51(3), 700-703. doi:10.1002/anie.201106562

Doménech, A., Doménech-Carbó, M. T., Sánchez del Río, M., Goberna, S., & Lima, E. (2009). Evidence of Topological Indigo/Dehydroindigo Isomers in Maya Blue-Like Complexes Prepared from Palygorskite and Sepiolite. The Journal of Physical Chemistry C, 113(28), 12118-12131. doi:10.1021/jp900711k

Doménech, A., Doménech-Carbó, M. T., del Río, M. S., & de Agredos Pascual, M. L. V. (2008). Comparative study of different indigo-clay Maya Blue-like systems using the voltammetry of microparticles approach. Journal of Solid State Electrochemistry, 13(6), 869-878. doi:10.1007/s10008-008-0616-1

Doménech-Carbó, A., Doménech-Carbó, M. T., Valle-Algarra, F. M., Domine, M. E., & Osete-Cortina, L. (2013). On the dehydroindigo contribution to Maya Blue. Journal of Materials Science, 48(20), 7171-7183. doi:10.1007/s10853-013-7534-z

Doménech-Carbó, A., Valle-Algarra, F. M., Doménech-Carbó, M. T., Domine, M. E., Osete-Cortina, L., & Gimeno-Adelantado, J. V. (2013). Redox Tuning and Species Distribution in Maya Blue-Type Materials: A Reassessment. ACS Applied Materials & Interfaces, 5(16), 8134-8145. doi:10.1021/am402193u

Rondão, R., Seixas de Melo, J. S., Bonifácio, V. D. B., & Melo, M. J. (2010). Dehydroindigo, the Forgotten Indigo and Its Contribution to the Color of Maya Blue. The Journal of Physical Chemistry A, 114(4), 1699-1708. doi:10.1021/jp907718k

Tilocca, A., & Fois, E. (2009). The Color and Stability of Maya Blue: TDDFT Calculations. The Journal of Physical Chemistry C, 113(20), 8683-8687. doi:10.1021/jp810945a

Giustetto, R., Seenivasan, K., Bonino, F., Ricchiardi, G., Bordiga, S., Chierotti, M. R., & Gobetto, R. (2011). Host/Guest Interactions in a Sepiolite-Based Maya Blue Pigment: A Spectroscopic Study. The Journal of Physical Chemistry C, 115(34), 16764-16776. doi:10.1021/jp203270c

Giustetto, R., & Wahyudi, O. (2011). Sorption of red dyes on palygorskite: Synthesis and stability of red/purple Mayan nanocomposites. Microporous and Mesoporous Materials, 142(1), 221-235. doi:10.1016/j.micromeso.2010.12.004

Giustetto, R., Seenivasan, K., Pellerej, D., Ricchiardi, G., & Bordiga, S. (2012). Spectroscopic characterization and photo/thermal resistance of a hybrid palygorskite/methyl red Mayan pigment. Microporous and Mesoporous Materials, 155, 167-176. doi:10.1016/j.micromeso.2012.01.024

Sánchez del Río, M., Boccaleri, E., Milanesio, M., Croce, G., van Beek, W., Tsiantos, C., … García-Romero, E. (2009). A combined synchrotron powder diffraction and vibrational study of the thermal treatment of palygorskite–indigo to produce Maya blue. Journal of Materials Science, 44(20), 5524-5536. doi:10.1007/s10853-009-3772-5

Mondelli, C., Río, M. S. del, González, M. A., Magazzú, A., Cavallari, C., Suárez, M., … Romano, P. (2012). Role of water on formation and structural features of Maya blue. Journal of Physics: Conference Series, 340, 012109. doi:10.1088/1742-6596/340/1/012109

Dejoie, C., Martinetto, P., Dooryhée, E., Strobel, P., Blanc, S., Bordat, P., … Anne, M. (2010). Indigo@Silicalite: a New Organic−Inorganic Hybrid Pigment. ACS Applied Materials & Interfaces, 2(8), 2308-2316. doi:10.1021/am100349b

Dejoie, C., Martinetto, P., Dooryhée, E., Brown, R., Blanc, S., Bordat, P., … Anne, M. (2011). Diffusion Of Indigo Molecules Inside The Palygorskite Clay Channels. MRS Proceedings, 1319. doi:10.1557/opl.2011.924

Ovarlez, S., Giulieri, F., Chaze, A.-M., Delamare, F., Raya, J., & Hirschinger, J. (2009). The Incorporation of Indigo Molecules in Sepiolite Tunnels. Chemistry - A European Journal, 15(42), 11326-11332. doi:10.1002/chem.200901482

Ovarlez, S., Giulieri, F., Delamare, F., Sbirrazzuoli, N., & Chaze, A.-M. (2011). Indigo–sepiolite nanohybrids: Temperature-dependent synthesis of two complexes and comparison with indigo–palygorskite systems. Microporous and Mesoporous Materials, 142(1), 371-380. doi:10.1016/j.micromeso.2010.12.025

Franç, N. A., Giulieri, oise, Ovarlez, S., & Chaze, A. M. (2012). Indigo/sepiolite nanohybrids: stability of natural pigments inspired by Maya blue. International Journal of Nanotechnology, 9(3/4/5/6/7), 605. doi:10.1504/ijnt.2012.045334

Tsiantos, C., Tsampodimou, M., Kacandes, G. H., Sánchez del Río, M., Gionis, V., & Chryssikos, G. D. (2011). Vibrational investigation of indigo–palygorskite association(s) in synthetic Maya blue. Journal of Materials Science, 47(7), 3415-3428. doi:10.1007/s10853-011-6189-x

Lima, E., Guzmán, A., Vera, M., Rivera, J. L., & Fraissard, J. (2012). Aged Natural and Synthetic Maya Blue-Like Pigments: What Difference Does It Make? The Journal of Physical Chemistry C, 116(7), 4556-4563. doi:10.1021/jp207602m

Kumagai, Y., Tsurutani, Y., Shinyashiki, M., Homma-Takeda, S., Nakai, Y., Yoshikawa, T., & Shimojo, N. (1997). Bioactivation of lapachol responsible for DNA scission by NADPH-cytochrome P450 reductase. Environmental Toxicology and Pharmacology, 3(4), 245-250. doi:10.1016/s1382-6689(97)00019-7

Nasiri, H. R., Bolte, M., & Schwalbe, H. (2008). Electrochemical and crystal structural analysis ofα- and dehydro-α-lapachones. Natural Product Research, 22(14), 1225-1230. doi:10.1080/14786410701654925

Garkavtsev, I., Chauhan, V. P., Wong, H. K., Mukhopadhyay, A., Glicksman, M. A., Peterson, R. T., & Jain, R. K. (2011). Dehydro- -lapachone, a plant product with antivascular activity. Proceedings of the National Academy of Sciences, 108(28), 11596-11601. doi:10.1073/pnas.1104225108

Doménech-Carbó, A., Labuda, J., & Scholz, F. (2012). Electroanalytical chemistry for the analysis of solids: Characterization and classification (IUPAC Technical Report). Pure and Applied Chemistry, 85(3), 609-631. doi:10.1351/pac-rep-11-11-13

Hoffman, R. C., Zilber, R. C., & Hoffman, R. E. (2010). NMR spectroscopic study of the Murex trunculus dyeing process. Magnetic Resonance in Chemistry, 48(11), 892-895. doi:10.1002/mrc.2685

Laatsch, H., Thomson, R. H., & Cox, P. J. (1984). Spectroscopic properties of violacein and related compounds: crystal structure of tetramethylviolacein. Journal of the Chemical Society, Perkin Transactions 2, (8), 1331. doi:10.1039/p29840001331

Silva, J. F. M. da, Garden, S. J., & Pinto, A. C. (2001). The chemistry of isatins: a review from 1975 to 1999. Journal of the Brazilian Chemical Society, 12(3), 273-324. doi:10.1590/s0103-50532001000300002

Doménech-Carbó, A., Martini, M., de Carvalho, L. M., & Doménech-Carbó, M. T. (2012). Square wave voltammetric determination of the redox state of a reversibly oxidized/reduced depolarizer in solution and in solid state. Journal of Electroanalytical Chemistry, 684, 13-19. doi:10.1016/j.jelechem.2012.08.016

Doménech, A., Doménech-Carbó, M. T., Osete-Cortina, L., & Montoya, N. (2013). Application of solid-state electrochemistry techniques to polyfunctional organic–inorganic hybrid materials: The Maya Blue problem. Microporous and Mesoporous Materials, 166, 123-130. doi:10.1016/j.micromeso.2012.04.031

Bond, A. M., Marken, F., Hill, E., Compton, R. G., & Hügel, H. (1997). The electrochemical reduction of indigo dissolved in organic solvents and as a solid mechanically attached to a basal plane pyrolytic graphite electrode immersed in aqueous electrolyte solution. Journal of the Chemical Society, Perkin Transactions 2, (9), 1735-1742. doi:10.1039/a701003f

He, H., Ding, Z., & Shoesmith, D. W. (2009). The determination of electrochemical reactivity and sustainability on individual hyper-stoichiometric UO2+x grains by Raman microspectroscopy and scanning electrochemical microscopy. Electrochemistry Communications, 11(8), 1724-1727. doi:10.1016/j.elecom.2009.07.013

Guadagnini, L., Maljusch, A., Chen, X., Neugebauer, S., Tonelli, D., & Schuhmann, W. (2009). Visualization of electrocatalytic activity of microstructured metal hexacyanoferrates by means of redox competition mode of scanning electrochemical microscopy (RC-SECM). Electrochimica Acta, 54(14), 3753-3758. doi:10.1016/j.electacta.2009.01.076

Yasarawan, N., & van Duijneveldt, J. S. (2008). Dichroism in Dye-Doped Colloidal Liquid Crystals. Langmuir, 24(14), 7184-7192. doi:10.1021/la800849y

Pires, S. M. G., Paula, R. D., Simões, M. M. Q., Silva, A. M. S., Domingues, M. R. M., Santos, I. C. M. S., … Cavaleiro, J. A. S. (2011). Novel biomimetic oxidation of lapachol with H2O2 catalysed by a manganese(iii) porphyrin complex. RSC Advances, 1(7), 1195. doi:10.1039/c1ra00578b

Niehues, M., Barros, V. P., Emery, F. da S., Dias-Baruffi, M., Assis, M. das D., & Lopes, N. P. (2012). Biomimetic in vitro oxidation of lapachol: A model to predict and analyse the in vivo phase I metabolism of bioactive compounds. European Journal of Medicinal Chemistry, 54, 804-812. doi:10.1016/j.ejmech.2012.06.042

Ferraz, P. A. ., de Abreu, F. C., Pinto, A. V., Glezer, V., Tonholo, J., & Goulart, M. O. . (2001). Electrochemical aspects of the reduction of biologically active 2-hydroxy-3-alkyl-1,4-naphthoquinones. Journal of Electroanalytical Chemistry, 507(1-2), 275-286. doi:10.1016/s0022-0728(01)00439-9

Abreu, F. C., Goulart, M. O. F., & Brett, A. M. O. (2002). Reduction of Lapachones in Aqueous Media at a Glassy Carbon Electrode. Electroanalysis, 14(1), 29-34. doi:10.1002/1521-4109(200201)14:1<29::aid-elan29>3.0.co;2-a

Ngameni, E., Tonle, I. K., Nanseu, C. P., & Wandji, R. (2000). Voltammetry Study of 2-Hydroxy-3-isopropenyl-1,4-naphthoquinone Using a Carbon Paste Electrode. Electroanalysis, 12(11), 847-852. doi:10.1002/1521-4109(200007)12:11<847::aid-elan847>3.0.co;2-9

Goulart, M. O. F., Lima, N. M. F., Sant’Ana, A. E. G., Ferraz, P. A. L., Cavalcanti, J. C. M., Falkowski, P., … Liwo, A. (2004). Electrochemical studies of isolapachol with emphasis on oxygen interaction with its radical anions. Journal of Electroanalytical Chemistry, 566(1), 25-29. doi:10.1016/j.jelechem.2003.10.043

Jungbluth, G., Rühling, I., & Ternes, W. (2000). Oxidation of flavonols with Cu(II), Fe(II) and Fe(III) in aqueous media. Journal of the Chemical Society, Perkin Transactions 2, (9), 1946-1952. doi:10.1039/b002323j

Caamal-Fuentes, E., Torres-Tapia, L. W., Simá-Polanco, P., Peraza-Sánchez, S. R., & Moo-Puc, R. (2011). Screening of plants used in Mayan traditional medicine to treat cancer-like symptoms. Journal of Ethnopharmacology, 135(3), 719-724. doi:10.1016/j.jep.2011.04.004

Arnold, D. E., Bohor, B. F., Neff, H., Feinman, G. M., Williams, P. R., Dussubieux, L., & Bishop, R. (2012). The first direct evidence of pre-columbian sources of palygorskite for Maya Blue. Journal of Archaeological Science, 39(7), 2252-2260. doi:10.1016/j.jas.2012.02.036

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