摘要： Three novel pairs of 1,3-bis(pyrrol-2-yl)squaraine dyes, N-alkylated SQ1a?1b, and N-phenylated SQ2a?2b in which triphenylethylene moieties functionalized at 5-position of pyrrole, as well as SQ3a?3b with tetraphenylethylene (TPE) moieties attached at N-position of pyrrole, were synthesized. All six dyes were found not to exhibit aggregation-induced emission (AIE) properties. Spectrophotometric studies showed that N-TPE-functionalized SQ3a?3b exhibited much larger molar extinction coefficients (ε: 1.36?2.14 × 105 M?1 cm?1) than 5,5′-triphenylethylene-functionalized SQ1a?2b (ε: 2.17?8.22 × 104 M?1 cm?1). Surprisingly, SQ2b showed a remarkable red-shifted maximum absorption (λmax: 723 vs 631?652 nm) compared to that of other squaraine dyes. All six squaraine dyes selectively responded to the addition of thiol-containing biomolecules, such as cysteine and gluthatione, with the disappearance of λmax in the near-infrared region in their respective absorption spectra. Interestingly, the thiolated species of SQ3a?3b were AIE active, with the characteristic AIE emission of TPE at λmax = 484?490 nm upon addition of water. Further thiol sensing on solid supports was examined, indicating the potential applications of TPE-functionalized squaraine dyes as bioprobes for the detection of important thiol-containing biomolecules, with a clear change from aggregation-caused quenching to AIE.