Affiliation:
1. Chemical Faculty, Department of Inorganic Chemistry Gdansk University of Technology Narutowicza 11/12 Gdańsk 80–233 Poland
2. Academic Centre of Materials and Technology AGH University of Krakow al. Mickiewicza 30 Kraków 30–059 Poland
3. National Synchrotron Radiation Centre SOLARIS Jagiellonian University ul. Czerwone Maki 98 Kraków 30‑392 Poland
4. Unconventional Computing Lab University of the West of England Bristol BS16 1QY UK
Abstract
AbstractThiazolothiazoles (TzTzs) are planar, π‐conjugated heterocyclic compounds exhibiting unique structural and optoelectronic properties. In this study, a series of symmetrically substituted thiazolothiazole (TzTz) derivatives including imidazolyl, o‐vanillyl, p‐vanillyl, phenyl, thiazolyl, cinnamoyl, and trifluoromethylphenyl were synthesized and extensively characterized using X‐ray crystallography (XRD), Fourier‐transformed infrared (FTIR), nuclear magnetic resonance (NMR), and ultraviolet‐visible (UV‐Vis) spectroscopies, photoluminescence, X‐ray absorption near edge structure (XANES, S K‐edge), and density functional calculations. The compounds demonstrated diverse intermolecular interactions, including π⋅⋅⋅π stacking and chalcogen bonding, which directly influenced their optical properties and electronic band structures. Several derivatives displayed promising features such as large Stokes shifts over 0.4 eV in solution and up to 1 eV in solid state and reversible resistive switching behavior, positioning them as attractive candidates for use in optoelectronic devices and emerging memristive technologies.