2109805-70-9Relevant articles and documents
Unprecedented Nucleophilic Attack of Piperidine on the Electron Acceptor during the Synthesis of Push-Pull Dyes by a Knoevenagel Reaction
Pigot, Corentin,Noirbent, Guillaume,Peralta, Sébastien,Duval, Sylvain,Nechab, Malek,Gigmes, Didier,Dumur, Frédéric
, (2019)
An unprecedented nucleophilic addition of piperidine on an electron acceptor, namely, 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile is reported. This unexpected behavior was observed during the synthesis of push-pull dyes using the classical Knoevenagel reaction. To overcome this drawback, use of diisopropylethylamine (DIPEA) enabled to produce the expected dyes PP1 and PP2. The optical and electrochemical properties of the different dyes were examined. Theoretical calculations were also carried out to support the experimental results. To evidence the higher electron-withdrawing ability of this electron acceptor, a comparison was established with two dyes (PP3 and PP4) comprising its shorter analogue.
Non-fullerene acceptors based on fused-ring oligomers for efficient polymer solar cells: Via complementary light-absorption
Li, Renlong,Liu, Gongchu,Xiao, Manjun,Yang, Xiye,Liu, Xiang,Wang, Zhenfeng,Ying, Lei,Huang, Fei,Cao, Yong
, p. 23926 - 23936 (2017)
We designed and synthesized two novel non-fullerene small molecule acceptors (IDT-N and IDT-T-N) that consist of indacenodithiophene (IDT) as the electron-donating core and 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile (N) as a novel electron-withdrawing end group. IDT-N and IDT-T-N consisting of the naphthyl-based N group exhibited an expanded plane compared to phenyl-based indanone (INCN), which strengthened the intramolecular push-pull effect between the core donor unit and the terminal acceptor units. This strengthened effect resulted in a reduced bandgap that was beneficial for solar photon collection and increased short-circuit current density of the resulting devices. IDT-N and IDT-T-N exhibited red-shifted absorptions and smaller optical bandgaps than the corresponding phenyl-fused indanone end-capped chromophores. Both acceptors exhibited broad absorptions and energy levels that were well-matched with the donor materials. Polymer solar cells based on IDT-N and IDT-T-N and two representative polymer donors (PTB7-Th and PBDB-T) exhibited impressive photovoltaic performances. The devices based on the PBDB-T:IDT-N system exhibited a power conversion efficiency of up to 9.0%, with a short-circuit current density of 15.88 mA cm-2 and a fill factor of 71.91%. These results demonstrate that IDT-N and IDT-T-N are promising electron acceptors for use in polymer solar cells.
New push-pull dyes based on 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile: An amine-directed synthesis
Pigot, Corentin,Noirbent, Guillaume,Peralta, Sébastien,Duval, Sylvain,Bui, Thanh-Tuan,Aubert, Pierre-Henri,Nechab, Malek,Gigmes, Didier,Dumur, Frédéric
, (2020/01/21)
A series of twelve dyes have been designed using 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile as the electron acceptor. While using piperidine as a classical base for the Knoevenagel reaction, a nucleophilic attack of the amine on the formed push-pull chromophore occurred, producing an azafluorenone derivative. By varying the amine, a series of azafluorenones could be obtained. By using an aldehyde of extended conjugation, a spontaneous aromatization following the cyclization reaction could also be demonstrated. The optical and electrochemical properties of the different dyes were examined. Theoretical calculations were also carried out to support the experimental results.
