One prominent set of quinoline containing compounds are the cinchona alkaloids, in particular the historically important anti-malarial quinine. However, both the chromophore and overall architecture of quinine is relatively inflexible due to its isolation from a natural source, limiting the application of such species in the development of SARs. Further, while methods for the synthesis of cinchona alkaloids exist, they are often insufficiently modular to permit significant structural variation. We therefore considered whether structural analogues of quinine might demonstrate similar PL properties while being accessible via a more modular synthetic strategy. This would provide easy access to families of compounds possessing both variable chromophores and intramolecular distances, thus enabling the unpacking of the fundamental processes of through-space charge transfer (TSCT) between the cage nitrogen lone pair and quinoline unit. Together this would enable the development of a basic SAR around these parameters. Further, getting a greater handle on the propensity of forming this TSCT would have important impact on the study of dimeric, excimeric and exciplex systems for use in OLEDs and other applications where intramolecular and intermolecular interactions are crucial. These include use in fluorescence microscopy and biological imaging, where tuneable properties would permit control of wavelengths of excitation and emission, as well as the nature of charge transfer.