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En el presente Trabajo de Fin de Grado se ha llevado a cabo la preparación de compuestos derivados de tetrafenilmetano mediante métodos eficientes y que os permitan obtener nuestros productos sin hacer uso de purificaciones cromatográficas. Además de realizarse la síntesis de nuevos compuestos, se incluye la síntesis de todos los compuestos intermedios entre los que encontramos el tetraquis(4-nitrofenil)metano, tetraquis(4-aminofenil)metano y tetraquis(4-bromofenil)metano . El compuesto precursor de los nuevos compuestos sintetizados es el tetraquis(4-azidofenil)metano. Este compuesto es precursor para la construcción de complejos moleculares con geometrías tetraédricas. Gracias a la presencia del grupo azido en nuestro producto, se puedo llevar a cabo la síntesis de dos compuestos nuevos mediante el uso de la química click. De esta forma, dos nuevos compuestos con cargas positivas permanentes fueron sintetizados, uno con cuatro y otro con ocho cargas positivas. Ambos presentan además contraiones diferentes que influyen en la solubilidad del producto final.Parte de este trabajo también consta la parte dedicada a la caracterización de los compuestos, tanto intermedios como nuevos.

Synthesis of cyclodextrin derivatives suitable for binding to solid supports This presented doctoral thesis studies the preparation of new cyclodextrin (CD) derivatives suitable for binding to solid supports. This work aims to develop synthetic protocols for monosubstituted and selectively persubstituted CD derivatives possessing permanent positive charges. These compounds have the potential to be electrostatically bound to negatively charged supports, including silica gel, alumina, Nafion® , cation exchange resins, etc. Compared to the covalent bond, the advantages of this electrostatic binding are mainly the easiness of modification and maintenance. Dipping solid support for a defined time into a solution of charged CD derivatives should ensure the bond between positively and negatively charged partners. Thus, this thesis is divided into several parts. The first part covers the preparation of neopentyl skeleton compounds (anchors) bearing positive charges suitable for ionic bonding with negatively charged solid supports, and a reactive functional group suitable for a reaction with CD derivatives. The first partially successful synthetic tries are described, together with various leaving groups kinetic studies performed by NMR spectroscopy. The final synthesis of anchors developed with potential...

Cyclodextrins are well known supramolecular hosts used in a wide range of applications. Monosubstitution of native cyclodextrins in the position C-6 of a glucose unit represents the simplest method how to achieve covalent binding of a well-defined host unit into the more complicated systems. These derivatives are relatively easy to prepare; that is why the number of publications describing their preparations exceeds 1400, and the reported synthetic methods are often very similar. Nevertheless, it might be very demanding to decide which of the published methods is the best one for the intended purpose. In the review, we aim to present only the most useful and well-described methods for preparing different types of mono-6-substituted derivatives. We also discuss the common problems encountered during their syntheses and suggest their optimal solutions.

This work deals with the use of methoxymethyl protecting group in chemistry of cyclodextrins, where this group has not been used very often so far. The work deals with development of optimal methods for introduction and for subsequent removal of the group and shows its usefulness in the preparation of new 6I -O-monosubstituted cyclodextrin derivatives, which are hard to get by standard methods. Key words: cyclodextrin derivatives, methoxymethyl group, protecting group

This bachelor work concerns the use of methoxymethyl protecting group in chemistry of cyclodextrins, where this group has not been used very often so far. The work deals with development of optimal methods for introduction and for subsequent removal of the group and shows its usefulness in the preparation of new cyclodextrin derivatives. Precursors for the synthesis of cyclodextrin dimers. Key words: cyclodextrin derivatives, methoxymethyl group, protecting group

This contribution reports the design, synthesis, photochemical properties and drug inclusion capability of two novel β-cyclodextrin (βCD) conjugates, βCD-NBFNO1 and βCD-NBFNO2, covalently integrating an N-nitroso amino-nitro-benzofurazan in the primary and secondary hydroxyl rims of the βCD scaffold, respectively through flexible spacers of different length. Both βCD conjugates are water-soluble and release nitric oxide (NO) under the input of either blue or green light, with quantum yields ΦNO (blue) = 0.13, 0.31 and ΦNO (green) = 0.007, 0.013 respectively, the former representing the largest values ever reported for nonmetal-containing NO donors activatable by visible light. The good contrast between the fluorescence green emission of the chromogenic moiety after and before the NO release permits the easy and in real-time quantification of the amount of NO generated, without the addition of external fluorescent agents. Despite the presence of the appendages, these βCD derivatives are also able to complex betaxolol, a β-blocker drug widely used for the reduction of the intraocular pressure, with binding constants Kb = 500 ± 50 and 1100 ± 100 M−1, respectively, without affecting the photochemical performances. In view of the well-known vasodilator properties of NO, the present βCD derivatives represent intriguing candidates for biopharmaceutical research studies addressed to combined therapeutic ocular applications.