title: 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.
authors.affiliation: Department of Chemistry, The University of Texas at El Paso, El Paso, TX 79968, USA. kpannell@utep.edu.
authors.forename: Robinson I
authors.initials: RI
authors.lastname: Roacho
authors.forename: Alejandro
authors.initials: A
authors.lastname: Metta-Magaña
authors.forename: Eduardo
authors.initials: E
authors.lastname: Peña-Cabrera
authors.forename: Keith
authors.initials: K
authors.lastname: Pannell
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D003116:Color; D005456:Fluorescent Dyes / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D012997:Solvents / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D012997:Solvents; D013438:Sulfhydryl Compounds