Issue 4, 2015

Unprecedented one-pot sequential thiolate substitutions under mild conditions leading to a red emissive BODIPY dye 3,5,8-tris(PhS)-BODIPY

Abstract

The simple reaction of phenylthiol with 8-MeS-BODIPY (1) in dichloromethane was readily accomplished to form 8-PhS-BODIPY (2). If the reaction is performed in THF 3,8-bis(phenylthio)-BODIPY (3) and 3,5,8-tris(phenylthio)-BODIPY (4) are sequentially formed in an unprecedented reaction. This provides a simple new methodology for the introduction of the phenylthio-moiety in the 3- and 5-positions. Alkyl thiols do not form multi-thiolated products under identical conditions, as exemplified using EtSH, where only 8-EtS-BODIPY (5) is formed.

Graphical abstract: Unprecedented one-pot sequential thiolate substitutions under mild conditions leading to a red emissive BODIPY dye 3,5,8-tris(PhS)-BODIPY

Supplementary files

Article information

Article type
Communication
Submitted
04 Sep 2014
Accepted
13 Nov 2014
First published
13 Nov 2014

Org. Biomol. Chem., 2015,13, 995-999

Author version available

Unprecedented one-pot sequential thiolate substitutions under mild conditions leading to a red emissive BODIPY dye 3,5,8-tris(PhS)-BODIPY

R. I. Roacho, A. Metta-Magaña, E. Peña-Cabrera and K. Pannell, Org. Biomol. Chem., 2015, 13, 995 DOI: 10.1039/C4OB01892C

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