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>.

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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

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article

BOPYRENPY: A Modular Strategy toward Structurally Tunable Seven-Membered BF2-Chelated Chromophores

Daniel A. Heredia, Ana L. Moore, Sofía C. Santamarina, Anton Khmelnitskiy et al.
3 citations
Organic Letters
Luminescence and Fluorescent Materials
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article

BOPYRENPY: A Modular Strategy toward Structurally Tunable Seven-Membered BF2-Chelated Chromophores

Daniel A. Heredia, Ana L. Moore, Sofía C. Santamarina, Anton Khmelnitskiy, Edwin J. González López
article en
3 citations

Abstract

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>.

Organic LettersVol. 27(27)
Consejo Nacional de Investigaciones Científicas y Técnicas (AR), Universidad Nacional de Río Cuarto (AR), Arizona State University (US)
Consejo Nacional de Investigaciones Científicas y Técnicas, Secretaría de Ciencia y Técnica, Universidad Nacional de Río Cuarto
Openalex Percentile: Top 17%
Luminescence and Fluorescent Materials
1.55
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