Journal of the American Chemical Society 2006-11-15

Synthesis of 7-azaserotonin: its photophysical properties associated with excited state proton transfer reaction.

Pei-Wen Wu, Wan-Ting Hsieh, Yi-Ming Cheng, Ching-Yen Wei, Pi-Tai Chou

Index: J. Am. Chem. Soc. 128 , 14426, (2006)

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Abstract

We report the synthesis of 3-(2-aminoethyl)-5-ol-1H-pyrrolo[2,3-b]pyridine (7-azaserotonin), which may potentially serve as an agonist or antagonist of serotonin receptors. In alcohols, the solvent (e.g., ethanol) catalyzed proton-transfer reaction takes place for 7-azaserotonin in the excited state, resulting in dual emission. Conversely, excited-state deprotonation takes place in neutral aqueous solution. The unique excitation behavior makes 7-azaserotonin versatile as a potential bioprobe.