Fluorescent molecular rotors are a class of fluorophores whose emission intensity is sensitive to the ability of the local environment to restrict bond rotations. Recently, these fluorophores have been conjugated to D-amino acids to study bacterial growth and development, however, the existing probes lack optimized physical and fluorescent properties for this type of application. To address this issue, new and existing fluorescent molecular rotors were synthesized and comparatively evaluated in an environment with increasing viscosity. Fluorescent D-amino acid molecular rotors were designed and synthesized from taking the previously reported structures with a tetrahydroquinoline core which was modified to include a methylpyridinium moiety. A pair of new molecular rotors was also synthesized by extending conjugation with 5-formylthiophene-2-boronic acid via Suzuki-Miyaura coupling. The characterization study showed all probes were water-soluble, possessed red-shifted emission and excitation. and much improved viscosity sensitivity. Most recent imaging studies indicate the new ability to label gram negative bacteria as well as gram positive bacteria. Unfortunately, the probes possessed somewhat low thermal stability, and new probes are being synthesized to address this issue.

Synthesis and characterization of pyridinium-based D-amino acid fluorescent molecular rotors

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