Design and synthesis of phenothiazine and phenothiazine sulfone derivatives

Abstract

The design and synthesis of π-conjugated organic material consists multi-modular donor-acceptor system has played a prominent role in the area of photovoltaic and organic electronics. The particular assignment of donor and acceptor units in the molecular framework provides the tuned intramolecular charge transfer (ICT) transitions from the donor to the acceptor unit and also tunes the HOMO-LUMO energy levels and optical band gap. The -conjugated heteroarenes are of interest for the construction of multi-modular donor-acceptor systems, owing to their variety of optoelectronic applications due to the presence of sulfur (S) and nitrogen (N) hetero atoms. The donor-acceptor motifs based on S and N heterocyclic units such as benzothiadiazole, thiazoles, phenothiazines, benzothiazoles and many more has wide range of applications in the field of organic photovoltaic (OPVs), and organic field-effect transistors (OFETs). [2] Phenothiazine (PTZ) is a well-known building block in the heterocyclic donor family with the following characteristics: (i) strong electron-donating character; (ii) non-planar "butterfly" type conformation; (iii) tunable redox properties; (iv) availability of multiple sites and ease of functionalization; and (v) affordable and commercial availability. The hetero-tricyclic scaffold phenothiazine (PTZ), also known as 10H-phenothiazine (M.F.: C12H9NS, M.W. =199.27 g/mol), was first found by Bernthsen in 1883 (Figure 1). [2]