MilliporeSigma
  • Home
  • Search Results
  • Sensitive naked eye detection of hydrogen sulfide and nitric oxide by aza-BODIPY dyes in aqueous medium.

Sensitive naked eye detection of hydrogen sulfide and nitric oxide by aza-BODIPY dyes in aqueous medium.

Analytical chemistry (2014-08-26)
Nagappanpillai Adarsh, Megha S Krishnan, Danaboyina Ramaiah
ABSTRACT

With an objective to develop optical probes for biologically important anions and neutral molecules, we synthesized three novel NIR absorbing aza-BODIPY derivatives, 3a-3c, and have systematically tuned their photophysical properties by changing the peripheral substitution. A profound red-shift was observed in the absorption and fluorescence spectra of the aza-BODIPY dyes with the change in substitution from azido (3a) to amino (3b) to dimethylamino (3c) groups. Theoretical calculations of 3a-3c showed a consistent decrease in bandgap, which supports the observed spectral changes. The study of their interactions with various analytes revealed that the azido-aza-BODIPY 3a selectively interacts with hydrogen sulfide (H2S) when compared to other molecules. Uniquely, the detection of H2S can be visualized through a change in color from bright blue to purple with a detection limit of 0.5 ppm. The sensitivity of the probe was observed to be ~20-fold higher than the allowed exposure limits of H2S as defined by EPA (10 ppm). The aza-BODIPY derivative 3b, on the other hand, exhibited selective interactions with nitrite ions (NO2(-)) and nitric oxide (NO) in aqueous medium through a visible color change from blue to green with a sensitivity of 20 and 0.15 ppb, respectively. In contrast, the dimethylamino-aza-BODIPY derivative, 3c, showed negligible affinity for the anions and neutral molecules tested. By tuning the photophysical properties through the judicious functionalization, the aza-BODIPY dyes thus synthesized can be utilized for the sensitive on-site detection and analysis of H2S, NO2(-), and NO in the aqueous medium.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Potassium carbonate, 99.995% trace metals basis
Sigma-Aldrich
N,N-Diisopropylethylamine, purified by redistillation, 99.5%
Sigma-Aldrich
Sodium bicarbonate-12C, 99.9 atom % 12C
Supelco
Nitrite ion standard solution, 0.1 M NO2-, for ion-selective electrodes
Supelco
Nitrite ion standard solution, 0.01 M NO2-, for ion-selective electrodes
Sigma-Aldrich
Sodium nitrite, 99.999% trace metals basis
Sigma-Aldrich
Potassium carbonate, BioUltra, anhydrous, ≥99.0% (T)
Sigma-Aldrich
Potassium carbonate, meets USP testing specifications
Sigma-Aldrich
Veratraldehyde, ≥98%, FG
Supelco
Sodium carbonate concentrate, 0.1 M Na2CO3 in water, eluent concentrate for IC
Sigma-Aldrich
Sodium thiosulfate, ≥99.99% trace metals basis
Sigma-Aldrich
Sodium carbonate-12C, 99.9 atom % 12C
Sigma-Aldrich
Potassium carbonate, anhydrous, powder, 99.99% trace metals basis
Sigma-Aldrich
3,4-Dimethoxybenzaldehyde, 99%
Sigma-Aldrich
N,N-Diisopropylethylamine, ReagentPlus®, ≥99%
Supelco
Sodium carbonate concentrate, Na2CO3 72 mM in water, IC eluent concentrate (20x) for Metrosep A Supp 7
Supelco
Sodium nitrite, analytical standard
Supelco
Verapamil Related Compound E, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Potassium carbonate, anhydrous, free-flowing, Redi-Dri, ACS reagent, ≥99%
Sigma-Aldrich
Potassium carbonate, BioXtra, ≥99.0%
Sigma-Aldrich
Potassium carbonate, puriss. p.a., ACS reagent, anhydrous, ≥99.0% (T)
Sigma-Aldrich
Potassium carbonate, ACS reagent, ≥99.0%
Sigma-Aldrich
Potassium carbonate, anhydrous, free-flowing, Redi-Dri, ReagentPlus®, 99%
Sigma-Aldrich
Potassium carbonate, ReagentPlus®, 99%
Sigma-Aldrich
Sodium nitrite, ACS reagent, ≥97.0%
Sigma-Aldrich
Sodium nitrite, ReagentPlus®, ≥99.0%
Sigma-Aldrich
Potassium carbonate, meets analytical specification of Ph. Helv., puriss., anhydrous, granulated, 99-101% (calc. to the dried substance)
Sigma-Aldrich
Potassium carbonate, reagent grade, ≥98%, powder, −325 mesh
Sigma-Aldrich
N,N-Diisopropylethylamine, 99.5%, biotech. grade
Sigma-Aldrich
Sodium thiosulfate, ReagentPlus®, 99%