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Benzothioxanthene imide (<b>BTI</b>) has recently emerged as an interesting and promising block for organic electronics. In this contribution, we report on the impact of the <i>N</i>-annulation of the latter dye on the optoelectronic of π-extended molecular structures. To do so, the thiophene-diketopyrrolopyrrole was selected, as central π-conjugated core, and either end-capped with two <b>BTIs</b> or its <i>N</i>-annulated version, namely the <b>TCI</b>. While almost similar band gaps were measured for individual rylene imide dyes, significant differences were highlighted, and rationalized, on their π-extended counterparts.