Preparation and processing of molecular materials with optoelectronic properties

Resumen

Organic small molecules materials with optoelectronic properties are particularly attractive in the fields of organic solar cells and molecular electronics. Porphyrins and curcuminoids (CCMoids) are prospective candidates in these fields due to their modifiable chemical structures and outstanding properties. In this thesis, the design and preparation of these two families of molecules, together with their self-assembly abilities and potential applications have been studied. In chapter II, two metalloporphyrins (Zn(4R-PPP) and Zn(PPP)) containing long chiral or achiral moieties with carbonyl substituents in the four meso-positions of their porphyrin cores have been synthesized. Then, a complete study related to non-covalent multiporphyrin assemblies has been performed, and initial solution-processed bulk heterojunction organic solar cell experiments were presented. To extend the above study, in chapter III, new porphyrins (TEP and Zn(TEP)) with shorter carbonyl substituents have been investigated and the effect of the length of the ligands in intermolecular interactions was studied, searching how this factor affects as well the OSCs performance. With the same chiral centres in the meso-positions, a porphyrin Zn(4R-CPP) involving carboxylic groups was obtained in chapter IV. And the binary self-assembling systems based on its derivations were achieved through non-covalent interaction or ionic self-assembly towards their potential application as active components in nanomaterials. In Chapter V, CCMoids containing chiral groups, in a similar manner as chapter II, were synthesized. In addition, research towards the achievement of terminal acid groups from the hydrolyzation of the ester groups (as chapter IV shows) allowed the investigation of the possible creation of systems with different dimensionalities. Then in Chapter VI, the synthesis of CPs/networks was explored by the use of a CCMoid containing pyridine moieties at its endings (3Py-CCM). The last chapter is devoted to the design of new porphyrin derivatives containing sulphur-based anchoring groups for their application in single molecular electronics together with the study of their electronic properties in solution and solid state. In addition, a family of CCMoids has also been analysed in a similar manner as the porphyrin derivatives, with the aim of gathering information to improve their molecular design for electronic applications.