Near-infrared fluorescent aza-BODIPY dyes for sensing and imaging of pH from the neutral to highly alkaline range

The Analyst
Christoph StaudingerSergey M Borisov

Abstract

New aza-BODIPY pH indicators with spectral properties modulated solely by photoinduced electron transfer (PET) are presented. The pH sensitive hydroxyl group is located in the meta-position of a phenyl substituent with respect to the aza-BODIPY core, which eliminates the conjugation to the chromophore. The new dyes show reversible "on"-"off" fluorescence response upon deprotonation of the receptor but no changes in the absorption spectrum, which is in contrast to state-of-the-art indicators of the aza-BODIPY family. This eliminates potential changes in the efficiency of the inner filter effect and Förster resonance energy transfer (FRET) and makes the new dyes suitable acceptors in light harvesting systems used for ratiometric pH imaging. The introduction of electron-withdrawing or electron-donating groups into the receptor results in a set of indicators suitable for measurements from physiological (pH 7) to very alkaline (pH 13) conditions. The new sensors are particularly promising for monitoring of pH changes in concrete, as was recently shown elsewhere.

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Citations

Sep 14, 2019·Chemistry : a European Journal·Edurne Avellanal-ZaballaJ Cristobal Lopez
Jan 17, 2020·ChemPlusChem·Guochen BaoPeter A Tanner
Jul 14, 2021·Journal of Fluorescence·Keerthana SAnitha Varghese
Aug 25, 2020·The Journal of Organic Chemistry·Ishanka RajapakshaColleen N Scott
Sep 4, 2019·The Journal of Organic Chemistry·Chathuranga S L RathnamalalaColleen N Scott
Nov 5, 2020·Chemical Reviews·Andreas SteineggerSergey M Borisov
Dec 10, 2019·ACS Omega·Søren Dollerup NielsenKlaus Koren

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Methods Mentioned

BETA
NMR
column chromatography
FRET
a
light harvesting
chip

Software Mentioned

Euriso
top

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