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

Edwin J. Gonzalez; Sofia C. Santamarina; Anton Y. Khmelnitskiy; Ana L. Moore; Daniel A. Heredia

doi:10.1021/acs.orglett.5c02127

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

Edwin J. Gonzalez
, Sofia C. Santamarina
, Anton Y. Khmelnitskiy
, Ana L. Moore
, Daniel A. Heredia

Molecular Sciences, School of (SMS)

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

A modular Knoevenagel condensation between 2-formylpyrroles and cyanomethylpyridine derivatives, followed by a chelation reaction, enables the synthesis of seven-membered BF₂-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.

Original language	English (US)
Pages (from-to)	7384-7388
Number of pages	5
Journal	Organic Letters
Volume	27
Issue number	27
DOIs	https://doi.org/10.1021/acs.orglett.5c02127
State	Published - Jul 11 2025

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "BOPYRENPY: A Modular Strategy toward Structurally Tunable Seven-Membered BF2-Chelated Chromophores",

abstract = "A modular Knoevenagel condensation between 2-formylpyrroles and cyanomethylpyridine derivatives, followed by a chelation reaction, enables the synthesis of seven-membered BF2-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.",

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AU - Santamarina, Sofia C.

AU - Khmelnitskiy, Anton Y.

AU - Moore, Ana L.

AU - Heredia, Daniel A.

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AB - A modular Knoevenagel condensation between 2-formylpyrroles and cyanomethylpyridine derivatives, followed by a chelation reaction, enables the synthesis of seven-membered BF2-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.

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

Abstract

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