Triarylboron Anchored Luminescent Probes: Selective Detection and Imaging of Thiophenols in the Intracellular Environment.
Sudhakar PagidiNeena K KalluvettukuzhyPakkirisamy ThilagarPublished in: Langmuir : the ACS journal of surfaces and colloids (2018)
The advances in boron incorporated organics have captured overwhelming interest on account of their outstanding properties and promising applications in various fields. Mostly, triarylborane compounds (TAB) are exploited as sensors of F- and CN- anions at the expense of the intrinsic Lewis acidic nature of boron. New molecular probes 1 and 2 for detection of toxic thiophenol were designed by conjugating highly fluorescent borylanilines with the luminescent quencher 2,4-dinitrobenzene based sulfonamides (DNBS), wherein the electrophilicity of the DNBS moiety has been modulated by fine-tuning the intrinsic Lewis acidity of boron. The interplay between PET (photoinduced electron transfer) and ICT have been employed for developing the TAB tethered turn-on fluorescent sensor for thiophenol with high selectivity for the first time. The newly developed probes showed very fast response toward thiophenol (within ∼5 min) with limits of detection (LOD) lying in the micromolar range, clearly pointing to their potential. Further, compounds 1 and 2 were explored for detecting thiophenol in the intracellular environment by discriminating biothiols. DFT and TD-DFT calculations were performed to support the sensing mechanism.
Keyphrases
- living cells
- fluorescent probe
- label free
- quantum dots
- electron transfer
- loop mediated isothermal amplification
- single molecule
- small molecule
- density functional theory
- sensitive detection
- fluorescence imaging
- real time pcr
- ionic liquid
- molecular docking
- computed tomography
- high resolution
- squamous cell carcinoma
- molecular dynamics
- photodynamic therapy
- lymph node metastasis
- molecular dynamics simulations
- air pollution
- positron emission tomography
- energy transfer
- metal organic framework
- human health
- climate change