Small molecule fluorescent probes are extensively use in imaging applications in biomedical research, material sciences and drug discovery. The diverse range of applications of small molecule fluorophores necessitates the design of molecules with specific photophysical profiles that are defined by their absorption wavelength (λmax,abs), emission wavelength (λmax,em) and quantum yield (Φ). The required absorption and emission wavelengths are based on the nature of the application, while higher quantum yields are generally preferred. Imaging applications such as multiplexed fluorescence microscopy benefit from incorporating multiple fluorophores with different emission wavelengths across the ultraviolet to infrared spectrum. Organic chromophores with infrared or near-infrared emissions are particularly attractive for biological imaging due to excellent tissue penetration and consequently better image quality. However, the design of low molecular weight red-emitters poses a significant challenge due to the difficulty of establishing small HOMO-LUMO energy gaps within compact conjugated systems. Control of λmax,abs and λmax,em values of molecular fluorophores can be effected primarily by structural modification of the chromophore scaffold which is a function of the synthetic tunability of the organic scaffold. Therefore, the development of novel heterocyclic motifs with a focus on facile and significant structural modularity is instrumental to designing platforms for custom fluorophore synthesis Historically, privileged fluorescent motifs such as coumarins, fluoresceins, BODIPY and rhodamines have been extensively studied for wavelength tunability but suffer from challenging scaffold modularity and limited rational design. Synthetically, such tunability is typically achieved through peripheral electronic modifications of the core structure, often resulting in minimal tunability of fluorescence emission wavelengths (Figure ). , More recently, novel heterocyclic cores showcasing high synthetic modularity through combinatorial screens have been developed to showcase tunable emission. A notable example of tunable fluorescence by Chenoweth and coworkers was showcased on a quinoline scaffold through a Suzuki-based library synthesis. While numerous electronic changes were effected through a peripheral disconnection approach (Figure ), only a small degree of emission tunability (90 nm, 482 nm -576 nm, 2.15 eV -2.57 eV) was observed. This underscores the need for versatile synthetic techniques capable of deep-seated scaffold modifications as well as functional modularity that allows for peripheral disconnections.