The thesis can be divided into two chapters: synthesis and application. The first chapter presents the basis of synthesis. Generally, electronic-deficient aromatic molecules require activation before reacting with metal reagents and then can go coupling reaction. Our lab has developed a new bipyridine coupling method without pre-functionalization of pyridines to the corresponding activated halide or metal forms or using of transition metal catalysts. This new method is quite efficient and advantageous for environmental protection. In second chapter, we synthesized 3,3¡¦-dihydroxy-2,2¡¦-bipyridine -based molecules and the functional groups were modified to investigate its liquid crystal properties. According to analyzing data of differential scanning calorimetry (DSC), polarized optical microscope (POM) and powder x-ray diffraction (XRD), we found that a-3 may possess cubic mesophaes with Im3m symmetry, and a series of d-1~d-3 compounds exhibit mesophase and may be further identified as smectic phase.

Azobenzene upon photochemical E/Z isomerization changes both its shape and size. The E-azobenzene moiety falls in the class of calamitic liquid crystalline mesogens, producing a wide variety of mesophases. Two series of linear bis(azobenzene) compounds, one with phenyl benzoate linkage and the other with benzyl benzoate linkage were synthesized. The termini of these molecules ranged from a dodecyloxy chain to hydrophobic amphiphilic dendrons up to first generation. We determined the effects of both the linkages and generation number on the mesogenic properties of these compounds. Our results show that the mesogenic behavior of these bis(azobenzene) compounds are highly dependent on the linkages between individual azobenzenes and that for the bis(azobenzene) compounds of the phenyl benzoate series, generation number had an effect on the liquid crystalline mesophase of the compounds

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Grace à leurs propriétés d’auto-réparation et d’auto-organisation, les matériaux pi-conjugués liquide-cristallins (LCs) présentent un grand intérêt pour l’élaboration de matériaux semi-conducteurs à hautes performances. Ils peuvent être utilisés pour différents types d’applications en électronique organique telles que les cellules solaires (OPV), les diodes électroluminescentes (OLED) et les transistors à effet de champs (OFET). Dans ce travail, nous avons conçu et préparé une nouvelle famille de LCs combinant des entités pi-conjuguées de type calamitique et discotique au sein d’une architecture moléculaire unique. Plus particulièrement, nous avons imaginé trois différentes architectures telles que des dyades et triades linéaires et des triades ramifiées, incluant des dérivés discotiques de pérylène ou de triphénylène et des dérivés calamitiques de terthiophène, de benzothienobenzothiophène ou encore de pyromellitique. L’objectif était d’étudier leurs comportements liquide-cristallins et leurs propriétés d’auto-organisation et de transport de charges.Les résultats obtenus ont montré que ces matériaux donnent des auto-assemblages complexes formant des arrangements multi-lamellaires de bicouches, dans lesquelles les entités calamitiques et discotiques présentent une organisation dans le plan. De plus, en choisissant judicieusement les entités pi-conjuguées calamitiques et discotiques (type-p ou type-n), nous avons démontré que ce type de matériaux auto-organisés peut présenter des propriétés de transport de charge ambipolaire en formant des chemins distincts pour chaque type de charge (trou et électron) par nano-ségrégation de ces entités de type p et de type n. / Due to their self-healing ability and their self-organization property, pi-conjugated liquid crystals (LCs) are materials of great interest to prepare high performance semiconducting materials. They can be used in different types of organic electronic applications such as solar cells (OPV), Organic Light-Emitting Diodes (OLED) and Organic Field-Effect Transistors (OFET). In this work, we were interested in designing and preparing a novel family of LCs combining π-conjugated discotic and calamitic moieties in a unique molecular architecture. More particularly, we designed three different molecular architectures based on a linear dyad, triad and a branched triad, which include discotic triphenylene or perylene and calamitic terthiophene, benzothienobenzothiophene or pyromellitic moieties. The objective was to study their liquid crystalline behaviors and their self-organization and charge transport properties.Based on our results, we demonstrated that these materials can form complex self-assemblies in the bulk such as multi-lamellar arrangements presenting bilayered lamellar phases with in-layer organization of both calamitic and discotic species. In addition, based on the appropriate choice of the disk- and rod-like π-conjugated cores (p-type or n-type), we showed that this kind of self-organized materials could exhibit ambipolar charge transport properties, presenting a spontaneous nanosegregation of p-type and n-type entities in bulk, and leading to well-defined distinct conductive channels for each type of charge carriers (hole and electron).