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  • Straightforward synthesis of oligopyrroles through a regioselective S(N)Ar reaction of pyrroles and halogenated boron dipyrrins.

Straightforward synthesis of oligopyrroles through a regioselective S(N)Ar reaction of pyrroles and halogenated boron dipyrrins.

Organic letters (2014-03-29)
Ting Jiang, Ping Zhang, Changjiang Yu, Jian Yin, Lijuan Jiao, En Dai, Jun Wang, Yun Wei, Xiaolong Mu, Erhong Hao
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.

MATERIALS
Product Number
Brand
Product Description

Boron, monofilament, 5m, diameter 0.1mm
Boron, monofilament, 20m, diameter 0.2mm
Boron, monofilament, 50m, diameter 0.1mm
Boron, monofilament, 200m, diameter 0.1mm
Boron, microfoil, disks, 25mm, thinness 0.1μm, specific density 23.5μg/cm2, permanent mylar 3.5μm support, 99.6%
Boron, monofilament, 20m, diameter 0.1mm
Boron, monofilament, 5m, diameter 0.2mm
Boron, monofilament, 100m, diameter 0.1mm
Boron, monofilament, 10m, diameter 0.1mm
Boron, microfoil, disks, 10mm, thinness 0.1μm, specific density 23.5μg/cm2, permanent mylar 3.5μm support, 99.6%
Boron, monofilament, 10m, diameter 0.2mm
Boron, monofilament, 50m, diameter 0.2mm
Sigma-Aldrich
Boron, crystalline, 1 cm, 99.7% trace metals basis
Sigma-Aldrich
Boron, crystalline, −60 mesh, 99% trace metals basis
Sigma-Aldrich
Boron, ≥95% (boron), amorphous powder