22734-61-8Relevant articles and documents
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.
ORGANIC SOLAR CELL AND PHOTODETECTOR MATERIALS AND DEVICES
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Paragraph 0080; 0257, (2020/11/30)
Narrow bandgap n-type small molecules are attracting attention in the near-infrared organic optoelectronics field, due to their easy tunable energy band with a molecular design flexibility. However, only a few reports demonstrate narrow bandgap non-fullerene acceptors (NFAs) that perform well in organic solar cells (OSCs), and the corresponding benefits of NFA photodiodes have not been well investigated in organic photodetectors (OPDs). Here, the ultra-narrow bandgap NFAs CO1-4F, CO1-4Cl and o-IO1 were designed and synthesized for the achieved efficient near-infrared organic photodiodes such as solar cells and photodetectors. Designing an asymmetrical CO1-4F by introducing two different π-bridges including alkylthienyl and alkoxythienyl units ultimately provides an asymmetric A-D′-D-D″-A molecular configuration. This enables a delicate modulation in energy band structure as well as maintains an intense intramolecular charge transfer characteristic of the excited state.
Spiroconjugated Donor-σ-Acceptor Charge-Transfer Dyes: Effect of the ?-Subsystems on the Optoelectronic Properties
Esser, Birgit,W?ssner, Jan S.
, p. 5048 - 5057 (2020/05/01)
Charge-transfer-based materials with intramolecular donor-acceptor structures are attractive for technological applications. Herein, a series of donor-σ-acceptor dyes has been prepared in a modular approach. The design of these intramolecular charge-transfer dyes is based on the concept of spiroconjugation, which leads to unique materials with special optical properties. The optical transitions are based on intramolecular charge transfer, as shown by solvatochromic measurements and density functional theory (DFT) calculations. Crystallographic, computational, electrochemical, and optical studies were performed to clarify the effect of different perpendicular ?-moieties on the optoelectronic properties. Our molecular tuning allowed for the synthesis of molecules exhibiting strong visible-range absorption. The compounds are not fluorescent due to structural changes in the excited state, as revealed by DFT calculations. Finally, our study describes enantiomerically pure spiroconjugated absorber molecules using 1,1′-binaphthyl-2,2′-diol (BINOL) units on the donor part.
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
, (2019/11/29)
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.
An A-D-A Type Small-Molecule Electron Acceptor with End-Extended Conjugation for High Performance Organic Solar Cells
Feng, Huanran,Qiu, Nailiang,Wang, Xian,Wang, Yunchuang,Kan, Bin,Wan, Xiangjian,Zhang, Mingtao,Xia, Andong,Li, Chenxi,Liu, Feng,Zhang, Hongtao,Chen, Yongsheng
, p. 7908 - 7917 (2017/10/03)
A new non-fullerene small molecule with an acceptor-donor-acceptor (A-D-A) structure, FDNCTF, incorporating fluorenedicyclopentathiophene as core and naphthyl-fused indanone as end groups, was designed and synthesized. Compared with the previous molecule FDICTF with the phenyl-fused indanone as the end groups, the extended π-conjugation at the end group has only little impact on its molecular orbital energy levels, and thus, the open-circuit voltage (Voc) of its solar cell devices has been kept high. However, its light absorption and mobility, together with the short-current density (Jsc) and the fill factor (FF), of its devices have been all improved simultaneously. Through morphology, transient absorption, and theoretical studies, it is believed that these favorable changes are caused by (1) the appropriately enhanced molecular interaction between donor/acceptor which makes the charge separation at the interface more efficient, and (2) enhanced light absorption and more ordered packing at solid state, all due to the extended end-group conjugation of this molecule. With these, the solar cells with FDNCTF as the acceptor and a wide band gap polymer PBDB-T as the donor demonstrated a high power conversion efficiency (PCE) of 11.2% with an enhanced Jsc and a maintained high Voc, and significantly improved FF of 72.7% compared with that of the devices of FDICTF with the phenyl-fused indanone as the end groups. These results indicate that the unexplored conjugation size of the end group plays a critical role for the performance of their solar cell devices.
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 (2017/11/30)
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.
Anti-allergic pharmaceutical compositions
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, (2008/06/13)
2-Nitroindane-1,3-dione derivatives are useful in the prophylaxis and treatment of asthma, hay fever and also in the treatment of rhinitis.
