Solvent-Free Synthesis and Fluorescence of a Thiol-Reactive Sensor for Undergraduate Organic Laboratories

Document Type



Harvey Mudd College, Chemistry (HMC)

Publication Date

Fall 11-8-2013


A green organic laboratory experiment was developed in which students synthesize a sensor for thiols using a microscale, solventless Diels–Alder reaction at room temperature or 37 °C. The molecular probe is easily purified by column chromatography in a Pasteur pipet and characterized by thin-layer chromatography and NMR spectroscopy. The thiol-reactive sensor becomes intensely fluorescent upon exposure to thiols from N-acetylcysteine, bovine serum albumin, or human hair (pretreated with a reducing agent to reveal cysteine thiols in α-keratin). This fluorescence is observable even with micrograms of probe.

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© 2013, ACS Publications