A bacteriochlorin-diketopyrrolopyrrole triad as a donor for solution-processed bulk heterojunction organic solar cells
We have designed an A–π–D–π–A small-molecule triad consisting of a bacteriochlorin (BC) donor central core linked with two diketopyrrolopyrrole (DPP) acceptors via ethynyl bridges (BC-DPP-1). BC-DPP-1 has a narrow optical bandgap of 1.38 eV with highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of −4.93 eV and −3.40 eV, respectively, and it was used as an electron donor along with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as an acceptor for solution-processed small-molecule organic solar cells. After optimizing the weight ratio between BC-DPP-1 and PC71BM and pyridine as a solvent additive and subsequent solvent vapor annealing using THF, an …
Design, Synthesis and Evaluation of Enzyme-Responsive Fluorogenic Probes Based on Pyridine-Flanked Diketopyrrolopyrrole Dyes
The ever-growing demand for fluorogenic dyes usable in the rapid construction of analyte-responsive fluorescent probes, has recently contributed to a revival of interest in the chemistry of diketopyrrolopyrrole (DPP) pigments. In this context, we have explored the potential of symmetrical and unsymmetrical DPP derivatives bearing two or one 4-pyridyl substituents acting as optically tunable group(s). The unique fluorogenic behavior of these molecules, closely linked to N-substitution/charge state of their pyridine unit (i.e., neutral pyridine or cationic pyridinium), has been used to design DPP-based fluorescent probes for detection of hypoxia-related redox enzymes and penicillin G acylase …
Near-infrared emissive bacteriochlorin-diketopyrrolopyrrole triads: Synthesis and photophysical properties
International audience; The synthesis of unprecedented energy transfer triads containing a near-infrared (NIR) emissive bacteriochlorin subunit and two diketopyrrolopyrrole (DPP) moieties linked to each other via ethynyl or zero-carbon spacers is presented. Their optical and fluorescence properties were determined in CHCl3 and toluene. These photophysical measurements highlight the ability of DPP scaffold to act as an effective energy donor, which once excited in the range 450-550 nm resulting nearly exclusively NIR emission of hydroporphyrin (ETE > 96%). Since DPP dyes are valuable structurally tunable fluorophores that may be used in the construction of high-performance multicomponent pho…
Bacteriochlorin-diketopyrrolopyrrole (DPP) hybrids : New near-infrared fluorophores for biosensing/bioimaging applications
Near-infrared (700-900 nm) absorbing and emitting organic-based fluorophores are valuable tools for bioimaging applications. Indeed, biological component absorption, diffusion and autofluorescence are quite low in this region (known as the first therapeutic window NIR-I), making tissues relatively transparent to these long wavelengths. Bacteriochlorins are porphyrins derivatives in which two double bonds are reduced. These molecules display a strong absorption and emission within NIR-I spectral range. DPPs are structurally simpler fluorophores displaying very interesting properties. They have high fluorescence quantum yields, are highly (photo)chemically and thermally stable. The aim of thi…
CCDC 1910052: Experimental Crystal Structure Determination
Related Article: Flavien Ponsot, Léo Bucher, Nicolas Desbois, Yoann Rousselin, Pritam Mondal, Charles H. Devillers, Anthony Romieu, Claude P. Gros, Rahul Singhal, Ganesh D. Sharma|2019|J.Mater.Chem.C|7|9655|doi:10.1039/C9TC02724F