A borindolizine platform for the design of fluorophores with tunable emissions
Journal article, 2025
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 fluorophores with desirable spectroscopic properties through the borindolizine scaffold.
Design and application
Synthesised
Emissions trends
Particulate emissions
Blue-emitting
Tunable emissions
Tunables
Stokes shift
Spectral prediction model
Spectroscopic property
Scaffolds
Red emissive
Author
Chirag N. Apte
University of Toronto
Nicholas W. Heller
University of Toronto
Ben Zhen Huang
University of Toronto
Adam Marr
University of Toronto
Kjell Jorner
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
University of Toronto
Alán Aspuru-Guzik
University of Toronto
Andrei K. Yudin
University of Toronto
Chemical Science
2041-6520 (ISSN) 2041-6539 (eISSN)
Vol. In PressInverse design of molecules and reactions
Swedish Research Council (VR) (2020-00314), 2021-01-01 -- 2023-12-31.
Subject Categories (SSIF 2025)
Theoretical Chemistry
Organic Chemistry
Physical Chemistry
DOI
10.1039/d5sc04328j
PubMed
41019652