A new strategy is
presented to preclude aggregation and enhance
water solubility of cyanine dyes. Namely, a heteroatom-containing
substituent, for distorting molecular plane and increasing interaction
with water molecules, is introduced to the methine chain of 2-thiazole
orange (1, a monocyanine) via one-step, and 2-thiazole
orange derivatives 2a–g are prepared
accordingly. The X-ray crystal structures show that the molecular
plane of 2a–g is drastically twisted,
which reduces intermolecular π–π stacking. The
derivatives 2a–g exhibit good to
excellent water solubility and can be dissolved in aqueous phosphate-buffered
saline (PBS) at concentrations suitable for biomedical applications.
No aggregation in aqueous PBS, relatively high molar extinction coefficients,
and low solvatochromism of 2a–g are
reflected by the UV–vis spectra. Compound 2b shows
fast response and high selectivity for biothiols (Cys, Hcy, and GSH)
in aqueous PBS and is further employed to detect endogenous biothiols
with decent biocompatibility as demonstrated by live cell fluorescence
imaging.