Strategic Construction of -Aryl-Substituted -Carbonyl-Bridged Dipyrrinones as Small, Bright, and Tunable Fluorophores.

Org Lett

Anhui Laboratory of Molecule-Based Materials; The Key Laboratory of Functional Molecular Solids, Ministry of Education; School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002, China.

Published: March 2024

AI Article Synopsis

  • Researchers developed new carbonyl-bridged dipyrrinone fluorophores using α-halogenated dipyrrinones sourced from a simple acid-catalyzed process.* -
  • This method allows for effective modifications of functional groups at key positions on the fluorophores, enhancing their properties.* -
  • The resulting dyes display adjustable absorption and emission wavelengths, strong light absorption, high efficiency in fluorescence, and have been successfully used in imaging living cells with advanced microscopy techniques.*

Article Abstract

A series of novel ,-carbonyl-bridged dipyrrinone fluorophores have been directly constructed from α-halogenated dipyrrinones, which are conveniently obtained from the acid-catalyzed hydrolysis of readily available α,α'-dihalodipyrrins. This novel methodology affords efficient modulation of the functional groups at both the - and α-positions of this fluorophore. These resultant dyes show tunable absorption and emission wavelengths, good molar absorption coefficients, relatively large Stokes shifts, and excellent fluorescence quantum yields up to 0.99, and have been successfully applied in both one- and two-photon fluorescence microscopy imaging in living cells.

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http://dx.doi.org/10.1021/acs.orglett.3c04324DOI Listing

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