Journal Article Epublish 5 citations
PubMed: 40201165 DOI: 10.1039/d5sc01131k
Search for improved triplet-state quenchers for fluorescence imaging: a computational framework incorporating excited-state Baird-aromaticity.
Chem Sci 16(18):7989-8001
Authors: Ouissam El Bakouri, Matthew A Johnson, Joshua R Smith, Avik K Pati, Maxwell I Martin, Scott C Blanchard, Henrik Ottosson
Affiliations
- Department of Chemistry -Ångström, Uppsala University Uppsala Sweden. Institut de Química Computacional i Catàlisi (IQCC), Departament de Química, Universitat de Girona C/Maria Aurèlia Capmany 6 17003 Girona Catalonia Spain.
- Department of Chemistry -Ångström, Uppsala University Uppsala Sweden.
- Department of Chemistry & Biochemistry, Cal Poly Humboldt Arcata CA 95501 USA.
- Department of Structural Biology, St. Jude Children's Research Hospital Memphis USA.
- Department of Chemistry, Birla Institute of Technology and Science Pilani Rajasthan 333031 India.
Abstract
Fluorescence imaging is crucial for studying biology. Triplet state quenchers (TSQs), especially cyclooctatetraene (COT), can dramatically improve fluorophore performance, particularly when linked intramolecularly so as to enable "self-healing". Leveraging knowledge revealed through investigations of the self-healing mechanism enabled by COT, we computationally screened for cyclic 8π-electron species, and their annulated derivatives, with efficient triplet-triplet energy transfer potential, high photostability, and strong spin-orbit coupling (SOC) between the lowest triplet state to the singlet ground state. Here, we report theory-based analyses of a broad array of candidates that demonstrate various extents of triplet state Baird-aromaticity, indicating self-healing potential. We identify specific candidates with 7-membered ring structures predicted to exhibit favorable enhancements in fluorophore performance spanning the visible spectrum, with several possessing estimated intersystem crossing (ISC) rates up to 4 × 10 times faster than that of COT, the current benchmark for the self-healing strategy.