Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 21, Pages 13529-13543Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01665
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Funding
- Foundation for Polish Science [POIR. 04.04.00-00-3CF4/16-00]
- COST [CHAOS CA 15106]
- Global Research Laboratory Program through the National Research Foundation (NRF) - Ministry of Science, ICT & Future Planning (Korea) [2014K1A1A2064569]
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A thorough investigation has enabled the optimization of the synthesis of 1,4-dihydro-pyrrolo[3,2-b]pyrroles. Although salts of such metals as vanadium, niobium, cerium, and manganese were found to facilitate the formation of 1,4-dihydro-pyrrolo[3,2-b]pyrroles from amines, aldehydes, and diacetyl, we confirmed that iron salts are the most efficient catalysts. The conditions identified (first step: toluene/AcOH = 1:1, 1 h, 50 degrees C; second step: toluene/AcOH = 1:1, Fe(ClO4)(3)center dot H2O, 16 h, 50 degrees C) resulted in the formation of tetraarylpyrrolo[3,2-b]pyrroles in a 6-69% yield. For the first time, very electron-rich substituents (4-Me2NC6H4, 3-(OH)C6H4, pyrrol-2-yl) originating from aldehydes and sterically hindered substituents (2-ClC6H4, 2-BrC6H4, 2-CNC6H4, 2-(CO2Me)C6H4, 2-(TMS-C C)C6H4) present on anilines can be appended to the pyrrolo[3,2-b]pyrrole core. It is now also possible to prepare 1,4-dihydropyrrolo[3,2-b]pyrroles bearing an ordered arrangement of N-substituents and C-substituents ranging from coumarin, quinoline, phthalimide to truxene. These advances in scope enable independent regulations of many desired photophysical properties, including the Stokes shift value and emission color ranging from violet-blue through deep blue, green, yellow to red. Simultaneously, the optimized conditions have finally allowed the synthesis of these extremely promising heterocycles in amounts of more than 10 g per run without a concomitant decrease in yield or product contamination. Empowered with better functional group compatibility, novel derivatization strategies were developed.
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