We report the synthesis and optical characterisation of different triphenylamine-based hole capture materials able to anchor to CdSe quantum dots (QDs). Cyclic voltammetry studies indicate that these materials exhibit reversible electrochemical behaviour. Photoluminescence and transient absorption spectroscopy techniques are used to study interfacial charge transfer properties of the triphenylamine functionalized CdSe QDs. Specifically, we show that the functionalized QDs based on the most easily oxidised triphenylamine display efficient hole-extraction and long-lived charge separation. The present findings should help identify new strategies to control charge transfer QD-based optoelectronic devices.