Synthesis and Properties of Ladder-Type BN-Heteroacenes and Diazabenzoindoles Built on a Pyrrolopyrrole Scaffold

A simple, three-step synthesis of BN-heteroacenes and diazabenzoindoles based on the pyrrole­[3,2-b]­pyrrole scaffold has been developed. The incorporation of BN units has proven to be effective in modulating the electronic properties and molecular geometries of the π-conjugated backbone, creating a...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-08, Vol.81 (15), p.6580-6586
Main Authors: Tasior, Mariusz, Gryko, Daniel T.
Format: Article
Language:English
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Summary:A simple, three-step synthesis of BN-heteroacenes and diazabenzoindoles based on the pyrrole­[3,2-b]­pyrrole scaffold has been developed. The incorporation of BN units has proven to be effective in modulating the electronic properties and molecular geometries of the π-conjugated backbone, creating a new type of heteroarenes. The unique planar structure and high rigidity of BN-compounds result in very high absorption coefficients and high fluorescence quantum yields, and, at the same time, very small Stokes shifts. A striking difference has been observed for a second type of derivatives: diazabenzoindoles, which remain virtually nonfluorescent, despite having a similar, rigid structure. The former class of heterocycles is characterized by a strong absorption around 400 nm and intense fluorescence observed in the 395–426 nm region, which results in very small Stokes shifts of less than 900 cm–1.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01209