title: Straightforward synthesis of oligopyrroles through a regioselective S(N)Ar reaction of pyrroles and halogenated boron dipyrrins.
abstract: A novel stepwise and regioselective nucleophilic aromatic substitution (SNAr) reaction of halogenated boron dipyrrins (BODIPYs) with pyrroles has been developed under mild conditions with no catalyst needed and shown to be diversity oriented. The resultant pyrrole-substituted BODIPYs are interesting red and near-infrared (NIR) fluorescent dyes with absorption maxima up to 733 nm. Removal of the BF2 protecting group of the 3-pyrrole or 3,5-dipyrrole-substituted BODIPYs provides a facial entry to oligopyrroles with direct 2,2'-bipyrrole linkages.
authors.affiliation: Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal University , Wuhu, Anhui 241000, China.
authors.forename: Ting
authors.initials: T
authors.lastname: Jiang
authors.forename: Ping
authors.initials: P
authors.lastname: Zhang
authors.forename: Changjiang
authors.initials: C
authors.lastname: Yu
authors.forename: Jian
authors.initials: J
authors.lastname: Yin
authors.forename: Lijuan
authors.initials: L
authors.lastname: Jiao
authors.forename: En
authors.initials: E
authors.lastname: Dai
authors.forename: Jun
authors.initials: J
authors.lastname: Wang
authors.forename: Yun
authors.initials: Y
authors.lastname: Wei
authors.forename: Xiaolong
authors.initials: X
authors.lastname: Mu
authors.forename: Erhong
authors.initials: E
authors.lastname: Hao
mesh_terms: D001895:Boron; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D019265:Spectroscopy, Near-Infrared
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D006843:Hydrocarbons, Chlorinated; D011758:Pyrroles; D001895:Boron