Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 11, Pages 5658-5665Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00618
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- Bavarian State Ministry of Science, Research, and the Arts for the Collaborative Research Network Solar Technologies go Hybrid
- Alexander von Humboldt Foundation
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We report a general and selective method to synthesize 2,7-disubstituted pyrene derivatives containing two different substituents by sequential Ir-catalyzed borylation and substitution chemistry. To demonstrate the utility of our approach, we synthesized 2-cyano-7-(N,N-diethylamino)pyrene (3); a pyrene analogue of the widely studied chromophore 4-(N,N-dimethylamino)benzonitrile (DMABN). Compound 3 and the monosubstituted compounds 2-(N,N-diethylamino)pyrene (1) and 2-cyanopyrene (2) have been structurally characterized. Their electronic and optical properties have been studied by a combination of absorption and emission spectroscopies, lifetime and quantum yield measurements, and modeling by DFT and TD-DFT. The photophysical properties of 3 are compared to those of DMABN and 2-cyano-7-(N,N-dimethylamino)-4,5,9,10-tetrahydropyrene, and we show that 2,7-disubstituted pyrene is a moderately effective pi-bridge for the construction of donor acceptor compounds. It is also shown that donor or acceptor groups are only effective at the 2,7-positions of pyrene if they are suitably strong, leading to a switch in the energetic ordering of the HOMO-1 and HOMO or the LUMO and LUMO+1 of pyrene, respectively.
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