SYNTHESIS AND CHARACTERIZATION OF 2,6-DIISOPROPYLPHENOXY TETRAPYRAZINOPORPHYRAZINES AS POTENTIAL MOLECULAR QUBITS

This thesis reports the synthesis of metal-free and metal-containing phthalocyanine derivatives using methods typical for that class of functional dyes. A mixture of the target compounds prepared here, one paramagnetic and one diamagnetic tetrapyrazinoporphyrazine, will be tested for their potential use in spintronics – the application of spin-active species in molecular electronics. Phthalocyanines and their derivatives are well-known for their ease of preparation and tunability; they have been utilized as sensitizers for photodynamic therapy of cancer and solar cells, as well as in catalysis and chemical sensing. Tetrapyrazinoporphyrazine complexes are compared with the parent phthalocyanine as their chemistry is similar but electronically are distinct. All compounds synthesized were investigated spectroscopically (UV-Vis, magnetic circular dichroism), electrochemically, and computationally; all methods showed the expected results typical of tetrapyrazinoporphyrazines. The paramagnetic vanadyl complex was confirmed by EPR spectroscopy and elucidated by single crystal X-ray diffraction. The green-colored macrocycles are substituted on their periphery by 2,6-diisopropylphenoxy groups; this creates a large nanoporous crystal stabilized by hydrophobic interactions that is useful for spintronic investigations. Under certain solvent conditions, a red linear trimeric product was isolated, and its optical properties and partial characterization is reported as well.