Organic electronics, pipe-dream few decades ago, is now a reality with commercially available Organic light emitting diode based displays (TVs, smartphones), sensors, batteries or photovoltaics (OPVs). Hence, the advent of such research field has generated a craze in the scientific community leading to the synthesis and characterization of various classes of pi-conjugated molecular and macromolecular semiconductors. Among them, imide-containing rylenes have attracted considerable research attention due to their redox, electron-withdrawing and charge-carrier transport properties, as well as their excellent chemical, thermal, and photochemical stabilities. Naphthalene diimide (NDI) and perylene diimide (PDI) can be unequivocally recognized as the most studied imide based building blocks for the preparation of high-performance electron transporting optoelectronic materials. Within these wide-ranging studies, considerable effort has been undertaken to functionalize both the bay positions and the nitrogen atom constituting the imide group (N-positions) to bring solubility, tune the molecular (opto)electronic characteristics, and build extended ?-conjugated architectures. A contrario, the N-(alkyl)benzothioxanthene-3,4-dicarboximide (BTXI), a sulfur containing rylene-imide dye, has not triggered such research interest. Among the very scarce publications, the later was exclusively dedicated to its remarkable fluorescent properties in biological and polymer staining applications. Moreover, from a chemical point of view, the BTXI was solely functionalized on the N-position for post-grafting purpose and/or to increase solubility resulting, once again due to a lack of interest, in limited range of characterizations and applications. In this context, and base on self-initiated fundamental work on the selective mono-bromination of the BTXI core, the aim of the BTXI-APOGEE project is to explore different synthetic methodologies to further functionalize the BTXI core, thus leading to the characterization of new and original molecular and macromolecular derivatives which will be finally embedded in specific devices namely OLEDs and organic solar cells.