Here we describe the design and applications of borindolizine, a novel scaffold with broadly tunable fluorescence and a high Stokes shift. Two classes of emitters were synthesized through rational scaffold modification, resulting in blue-emitting carboxyborindolizines (λmax,em = 431 – 459 nm) and green-emitting aryl borindolizines (λmax,em = 489 – 519 nm). Experimental structure-emission trends were used to validate a computational spectral prediction model and to subsequently design a red-emissive borindolizine scaffold. The red-emissive isoquinolyl borinidolizine was prepared, and the experimental emission (λmax,abs = 370 nm, λmax,em = 635 nm) was in excellent agreement with the theoretical emission (λmax,em = 646 nm). These results show how the application of data science can produce fluorphores with desirable spectroscopic properties using the borindolizine scaffold.
