An electron-deficient aromatic thiol bearing a strongly electron-withdrawing trifluoromethoxy group para to the –SH moiety. The OCF₃ substituent lowers the pKa of the thiol to ≈5.2, enhances oxidative stability and lipophilicity (clogP 3.6), while the oxygen spacer maintains π-conjugation for orthogonal reactivity. Key applications include:
High-index thiol–ene optical resins: photopolymerisation with triallyl isocyanurate yields colourless films (n = 1.65, Tg 128 °C, YI <1 after 500 h Q-UVB) for 5G lens substrates and OLED encapsulation layers.
Silver-antimicrobial self-assembled monolayers: the densely packed fluorinated surface (water contact angle 100°) sustains >99 % bacterial kill after 24 h and suppresses Ag tarnishing in saline atmospheres.
Palladium-selective scavenger: the soft sulfur and electron-poor ring form a stable Pd(II) complex (log K = 18.9), enabling recovery of Pd from spent cross-coupling liquors to <0.1 ppm residual.
Electrophilic thiolation reagent: the pre-activated ArS⁻ species transfers cleanly to electron-rich arenes under oxidative conditions, furnishing unsymmetrical diaryl sulfides for OLED host materials.
Redox-cleavable bioconjugate linker: the quinone–thiol redox potential (E°′ –0.16 V vs NHE) triggers glutathione-mediated release of cytotoxic payloads in tumour cytosol.
Store under nitrogen at 2–8 °C, away from light and oxidants to prevent disulfide formation.
