Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 37, Pages 16104-16113Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202005244
Keywords
diketopyrrolopyrroles; donor-acceptor systems; dyes; pigments; fluorescence; lactams
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Funding
- Foundation for Polish Science [TEAM POIR.04.04.00-00-3CF4/16-00, START 98.2016]
- National Research Foundation (NRF) - Ministry of Science, ICT & Future Planning, Korea [2014K1A1A2064569]
- DFG [SFB 953]
- Free State of Bavaria (SolTech)
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Red-emissive pi-expanded diketopyrrolopyrroles (DPPs) with fluorescence reaching lambda=750 nm can be easily synthesized by a three-step strategy involving the preparation of diketopyrrolopyrrole followed by N-arylation and subsequent intramolecular palladium-catalyzed direct arylation. Comprehensive spectroscopic assays combined with first-principles calculations corroborated that both N-arylated and fused DPPs reach a locally excited (S-1) state after excitation, followed by internal conversion to states with solvent and structural relaxation, before eventually undergoing intersystem crossing. Only the structurally relaxed state is fluorescent, with lifetimes in the range of several nanoseconds and tens of picoseconds in nonpolar and polar solvents, respectively. The lifetimes correlate with the fluorescence quantum yields, which range from 6 % to 88 % in nonpolar solvents and from 0.4 % and 3.2 % in polar solvents. A very inefficient (T-1) population is responsible for fluorescence quantum yields as high as 88 % for the fully fused DPP in polar solvents.
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