Synthesis of new substituted organosulfur donors for the preparation of conductive and multifunctional materials

Doctoral thesis English OPEN
Zecchini, M (2015)

The work presented in this thesis focused on the preparation of three main type of compounds: i) bridged dimeric BEDT-TTF donors (chapter 2), ii) enantiopure substituted EDT-TTF donors with hydrogen bonding functionalities (chapter 3) and iii) BEDT-TTF substituted ligands and their ability to form multifunctional materials (chapter 4). In chapter 2 the preparation of novel BEDT-TTF donors containing an alkene in the side such as (I) and (II) is reported. Single crystals of oxidised material have been prepared and conductivities have been measured. A radical cation salt of (I) with I2/I3 was found to be a semiconductor at r.t. [Figure 1. Donors containing an alkene functionality on the side chain.]. The preparation of dimeric BEDT-TTFs such as (III) has been investigated using different substrates and strategies but the reactivity towards the second cyclisation was found to be the issue. [Figure 2. Desired dimer system (III).]. The chapter 3 contains the preparation of novel enantiopure EDT-TTF derivatives, whose side chains were designed to guide the packing in the solid state by involving non-covalent interactions such as hydrogen bonding and/or additional π-π stacking interactions as in donors (IV) and (V). [Figure 3. Examples of enantiopure donors prepared in chapter 3.]. In chapter 4 the investigation of the coordination chemistry of novel BEDT-TTF substituted ligand (VI) with first row transition metals has started. The magnetism of some of the new complexes formed has been measured. [Figure 4. Type of BEDT-TTF ligands designed for metal complexes preparation.].
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