We recently reported that photochemically-accessed tricyclic aziridines undergo efficient Pdcatalysed cascade processes to provide cage structures 5 (Scheme 1b) which, while initially lacking a quinoline chromophore, appeared to offer similar rigidity, functionality and N-aryl distances as those observed in quinine. Importantly, the modular nature of this synthesis enables facile interchange of the components employed within it. We therefore considered whether this system could be used as a quinine surrogate, enabling modification of the aryl chromophore via modification of allylic amine 4 together with variation of both N-aryl distance and the tetracyclic core via the substitution of tether 6 and aziridine 3 respectively (Scheme 1c). We thus undertook the synthesis of a range of quinolinecontaining allylic amines 6 in order to explore their Pd-catalysed reaction with aziridines 3 and develop a series of photophysical SARs focused around the switching on and off of charge transfer.