Organic photovoltaics (OPVs) have been investigated over the last decade due to the appeal of low-cost solution-processable renewable devices that utilize renewable energy. The efficiency of OPVs can be enhanced with materials that are capable of producing multiple excitons from a single absorbed photon (singlet fission). Recently, intramolecular singlet fission (iSF) has been reported in oligomers with an acceptor-donor-acceptor motif. Our group has previously shown that bridging conjugated compounds with sulfur bridges result in intramolecular change-transfer (CT), similar to the behaviour observed in compounds showing iSF. Herein, we propose the use of sulfoxide bridges to increase CT behaviour in trimers, promoting iSF. We report several new thiophene-containing conjugated trimers containing sulfur bridges and investigations of the photophysical behaviour of these compounds. Possible applications in singlet fission will be discussed.