Synthesis of 7-Azaserotonin: Its Photophysical Properties Associated with Excited State Proton Transfer Reaction | Zendy

Peiwen Wu | Zendy; WanTing Hsieh | Zendy; YiMing Cheng | Zendy; ChingYen Wei | Zendy; PiTai Chou | Zendy

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Synthesis of 7-Azaserotonin: Its Photophysical Properties Associated with Excited State Proton Transfer Reaction

Author(s) -

Peiwen Wu,

WanTing Hsieh,

YiMing Cheng,

ChingYen Wei,

PiTai Chou

Publication year - 2006

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja064310e

Subject(s) - chemistry , deprotonation , excited state , pyridine , proton , photochemistry , agonist , aqueous solution , solvent , receptor , organic chemistry , ion , biochemistry , physics , quantum mechanics , nuclear physics

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.

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