Analyte-Induced Restriction of Intramolecular Rotation: Turn-On aza-BODIPY Sensor for Biothiol Detection in Aqueous Media

Two alternate aza-BODIPY fluorophores bearing a formyl-functional group were synthesized and evaluated for biothiol sensing. Both provide high binding constants (up to 9800 M<sup>-1</sup>) and low limits of detection (as low as 1 μM). More importantly, this study introduces an unconventional "turn-on" sensing mechanism, in which fluorescence enhancement arises from analyte-induced restriction of intramolecular rotation rather than analyte-triggered cleavage of quencher. This alternative strategy provides a promising platform for the development of next-generation fluorescent probes.

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Publication Details

Journal
Organic Letters
Published
2025-08-27
DOI
https://doi.org/10.1021/acs.orglett.5c02543
Citations
2
Primary Topic
Sulfur Compounds in Biology
Type
article
Field-Weighted Citation Impact
2.22
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article

Analyte-Induced Restriction of Intramolecular Rotation: Turn-On aza-BODIPY Sensor for Biothiol Detection in Aqueous Media

Ayşe Daut Özdemir, Bleda Can Sadıkoğulları
2 citations
Organic Letters
Sulfur Compounds in Biology
2.22
article

Analyte-Induced Restriction of Intramolecular Rotation: Turn-On aza-BODIPY Sensor for Biothiol Detection in Aqueous Media

Ayşe Daut Özdemir, Bleda Can Sadıkoğulları
article en
2 citations

Abstract

Two alternate aza-BODIPY fluorophores bearing a formyl-functional group were synthesized and evaluated for biothiol sensing. Both provide high binding constants (up to 9800 M<sup>-1</sup>) and low limits of detection (as low as 1 μM). More importantly, this study introduces an unconventional "turn-on" sensing mechanism, in which fluorescence enhancement arises from analyte-induced restriction of intramolecular rotation rather than analyte-triggered cleavage of quencher. This alternative strategy provides a promising platform for the development of next-generation fluorescent probes.

Organic LettersVol. 27(36)
Division of Chemistry (US), Istanbul Technical University (TR)
Clean water and sanitation
Openalex Percentile: Top 11%
Sulfur Compounds in Biology
2.22
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