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Usage

Uses

Used in Pharmaceutical Research:
(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)propanedinitrile is used as a building block in pharmaceutical research for its potential use in anti-cancer drugs. Its unique structure and biological activity make it a promising candidate for the development of new cancer treatments.
Used in Organic Synthesis:
In the field of organic synthesis, (3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)propanedinitrile serves as a valuable building block due to its distinctive structure. This allows for the creation of various complex organic compounds and molecules.
Used in Material Development:
(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)propanedinitrile is also utilized in the development of new materials. Its unique properties contribute to the advancement of material science, potentially leading to the creation of innovative and improved materials.
Used in Dye Production:
(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)propanedinitrile has been studied for its potential use in the development of new dyes. Its yellow-orange color and unique structure make it a candidate for the creation of novel dyes for various applications.
Used in Medical Applications:
(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)propanedinitrile has been found to exhibit anti-inflammatory and antioxidant properties. These characteristics make it a promising candidate for various medical applications, potentially contributing to the development of new treatments and therapies.
Used in Industrial Applications:
(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)propanedinitrile's unique structure and properties also make it a promising candidate for various industrial applications. Its potential use in the development of new materials and dyes can have wide-ranging implications across different industries.

Upstream product

• 22734-61-8 1H-cyclopenta[b]naphthalene-1,3(2H)-dione 
• 109-77-3 malononitrile 
• 716-39-2 2,3-Naphthalenedicarboxylic anhydride 
• 127-09-3 sodium acetate 

Relevant academic research and scientific papers

Unprecedented Nucleophilic Attack of Piperidine on the Electron Acceptor during the Synthesis of Push-Pull Dyes by a Knoevenagel Reaction

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

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

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.

ORGANIC SOLAR CELL AND PHOTODETECTOR MATERIALS AND DEVICES

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.

New push-pull dyes based on 2-(3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)malononitrile: An amine-directed synthesis

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.