5 years ago

The Tetraarylpyrrolo[3,2-b]pyrrolesFrom Serendipitous Discovery to Promising Heterocyclic Optoelectronic Materials

The Tetraarylpyrrolo[3,2-b]pyrrolesFrom Serendipitous Discovery to Promising Heterocyclic Optoelectronic Materials
Dorota Gryko, Maciej Krzeszewski, Daniel T. Gryko
Progress in organic optoelectronics requires compounds possessing a suitable combination of photophysical and electronic properties. Another key constraint encompasses the availability of feasible, and hopefully scalable, synthetic procedures for preparing the molecular scaffolds of interest. A multicomponent reaction of aromatic aldehydes, aromatic amines, and butane-2,3-dione that was discovered in 2013 gives straightforward access to previously unavailable 1,2,4,5-tetraarylpyrrolo[3,2-b]pyrroles. These dyes are examples of heteropentalenes—a class of 10-π-electron aromatic compounds. The unsurpassed variety of aromatic aldehydes and primary aromatic amines, which are commercially available or easy to prepare, allows for potential routes to thousands of 1,2,4,5-tetraarylpyrrolo[3,2-b]pyrroles that are currently unknown. This synthetic procedure offers a means for preparing the pyrrolopyroles in gram quantities and isolating them by simple filtration.

Publisher URL: http://dx.doi.org/10.1021/acs.accounts.7b00275

DOI: 10.1021/acs.accounts.7b00275

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