BOPYRENPY: A Modular Strategy toward Structurally Tunable Seven-Membered BF<sub>2</sub>-Chelated Chromophores
A modular Knoevenagel condensation between 2-formylpyrroles and cyanomethylpyridine derivatives, followed by a chelation reaction, enables the synthesis of seven-membered BF<sub>2</sub>-chelated dyes, termed BOPYRENPY. This versatile strategy enhances structural diversity and functional applicability. In addition, our approach supports the late-stage incorporation of donor units via Suzuki coupling, allowing fine-tuning of fluorescence, Stokes shifts, and HOMO-LUMO energy levels. These findings establish BOPYRENPY as a versatile platform for next-generation chromophores based on 7-membered-ring dyes coordinated by BF<sub>2</sub>.
Authors
- Daniel A. Heredia (ORCID: https://orcid.org/0000-0002-0667-3906)
- Ana L. Moore (ORCID: https://orcid.org/0000-0002-6653-9506)
- Sofía C. Santamarina
- Anton Khmelnitskiy (ORCID: https://orcid.org/0000-0003-2018-9261)
- Edwin J. González López (ORCID: https://orcid.org/0000-0002-4680-1087)
Institutions
- Consejo Nacional de Investigaciones Científicas y Técnicas (AR)
- Universidad Nacional de Río Cuarto (AR)
- Arizona State University (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-30
- DOI
- https://doi.org/10.1021/acs.orglett.5c02127
- Citations
- 3
- Primary Topic
- Luminescence and Fluorescent Materials
- Type
- article
- Field-Weighted Citation Impact
- 1.55
Funders
- Consejo Nacional de Investigaciones Científicas y Técnicas
- Secretaría de Ciencia y Técnica, Universidad Nacional de Río Cuarto