ORCID
- Mikhail A. Filatov: 0000-0002-1640-841X
Abstract
A series of unsymmetrically substituted BODIPY dyes featuring fused benzo- or naphtho-fragments on one pyrrolic unit were synthesized from the corresponding pyrrolic precursors. The synthetic route was optimized using a modular approach based on the condensation of formylpyrroles with alkylpyrroles, enabling the identification of precursor combinations that minimize byproduct formation and improve preparative yields. The resulting benzo- and naphtho-fused BODIPYs display intense fluorescence in the red region, with emission maxima spanning 590–680 nm and fluorescence quantum yields ranging from 0.27 to 0.84. Their two-photon absorption (2PA) properties were studied both experimentally and computationally. An increase in the two-photon absorption cross-section with an increase in the size of the π-conjugated system was observed, reaching 80 GM for the naphthoBODIPY derivative. These findings demonstrate the potential of π-extended BODIPY scaffolds as NIR-active fluorophores with enhanced nonlinear optical properties.
DOI Link
Publication Date
2025-09-19
Publication Title
Journal of Organic Chemistry
Volume
90
Issue
37
ISSN
0022-3263
First Page
12984
Last Page
12997
Deposit Date
2026-02-24
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
Additional Links
Recommended Citation
Dvoracek, Metodej; Newman, Craig; Drobizhev, Mikhail; Twamley, Brendan; Senge, Mathias O.; Vinogradov, Sergei A.; and Filatov, Mikhail A., "Synthesis and Optical Properties of Unsymmetric Aromatically π-Extended BODIPY" (2025). Research Outputs: 2025-Present. 36.
https://arrow.tudublin.ie/scschcpsro/36