2099010-83-8

Usage

Physical state

Yellow solid

Usage

Organic synthesis, building block for heterocyclic compounds

Malononitrile group

Versatile intermediate in organic synthesis

Cyclopentathiophene moiety

Five-membered aromatic ring containing sulfur

Potential applications

Pharmaceutical, agrochemical, and material development

Unique structure

Contributes to its usefulness in various industries

Interesting properties

Valuable for research and development in organic chemistry

Upstream product

• 109-77-3 malononitrile 
• 246232-39-3 5H-cyclopenta[c]thiophene-4,6-dione 

Relevant academic research and scientific papers

Achieving high short-circuit current and fill-factor via increasing quinoidal character on nonfullerene small molecule acceptor

Recently, the fused-ring based low band gap (LBG) small molecule acceptors (SMAs) have emerged as efficient nonfullerene acceptors. So far, these LBG SMAs are mainly designed with IC (2-methylene-(3-(1,1-dicyanomethylene)indanone)) or its analogs, the benzo-type electron-accepting (A) units. Compared to benzene, thiophene is less aromatic and thus the thiophene-involving semiconducting molecule has more quinoidal character, which effectively reduces the energy gap between the highest occupied molecular orbit (HOMO) and the lowest unoccupied molecular orbit (LUMO). Herein, we show that replacing the IC units in ITIC with the CT (cyclopenta[c]thiophen-4-one-5-methylene-6-(1,1-dicyanomethylene)), a thiophene-fused A unit, the quinoidal character is enhanced from 0.0353 on ITIC to 0.0349 on ITCT, the CT-ended SMA. The increase in the quinoidal character reduces the optical band gap and enhances the near IR absorptivity. When blended with the wide band gap (WBG) polymer donor, PBDB-T, an average power conversion efficiency of 10.99% is obtained with a short-circuit current-density (Jsc) of 17.88 mA/cm2 and a fill-factor (FF) of 0.723. For comparisons, the Jsc is of 16.92 mA/cm2, FF is of 0.655 and PCE is of 9.94% obtained from the ITIC:PBDB-T device. This case indicates that the replacement of the benzene ring on the IC unit with a more polarizable five-member ring such as thiophene is an effective way to enhance the absorption of the near IR solar photons towards designing high-performance nonfullerene polymer solar cells.

Regulating exciton bonding energy and bulk heterojunction morphology in organic solar cells: Via methyl-functionalized non-fullerene acceptors

Electron-deficient end groups (EGs) are very important for non-fullerene small molecule acceptors (NF-SMAs) to tune their absorption, energy levels, and crystallization properties. Herein, we designed and synthesized three SMAs, namely, BTTIC-0M, BTTIC-2M, and BTTIC-4M by adding the methyl unit into 2-(6-oxo-5,6-dihydro-4H-cyclopenta[c]thiophen-4-ylidene)malononitrile (CPTCN). Methyl group, with its slight electron-donating ability, significantly elevates the LUMO energy levels but does not seriously affect the bandgaps of the CPTCN-based SMAs, which helps to reduce the energy loss (Eloss). In-depth dynamic theoretical simulations of the donor-acceptor (D-A) complex reveal that the exciton bonding energy (BE) can be fine-tuned by continuously increasing the methyl groups on the end groups of the SMAs. Methyl-substituted EG reduces the driving force and also enhances the BE of the charge transport (CT) state exciton, leading to a decrease in the exciton dissociation efficiencies. However, we found that one methyl-functionalized CPTCN enables PBDB-T:BTTIC-2M-based organic solar cells (OSCs) to achieve a power conversion efficiency (PCE) as high as 13.15%. Though PBDB-T:BTTIC-2M-based OSCs exhibit a slightly lower exciton dissociation efficiency than those of PBDB-T:BTTIC-0M, a more favorable superficial and internal morphology is attained in the PBDB-T:BTTIC-2M bulk-heterojunction layer, which balances the electron and hole mobilities and diminishes the bimolecular recombination. Comparatively, BTTIC-4M failed to realize a high performance owing to its adverse interactions with the polymer chain and the multiscale phase separation in the blend films. Actually, adjusting the number of methyl groups on the end group is done to compensate the current-voltage losses within the OSC devices with complicated contributions from absorption spectra, LUMO energy levels, exciton bonding energies, and morphologies.

Polyquinane-based conjugated macromolecule and preparation method and application thereof

The invention relates to the field of solar cells and optical detectors, in particular to polyquinane-based conjugated macromolecules and a preparation methods and application thereof. The conjugatedmacromolecule is a compound as shown in the formula (1).

Two-dimensional condensed ring conjugate large molecule, and preparation method and application thereof

The invention relates to the field of solar cells and optical detectors, in particular to a two-dimensional condensed ring conjugate large molecule, and a preparation method and application thereof. The two-dimensional condensed ring conjugate large molec

Many and fused ring conjugated macromolecule and its preparation method and application (by machine translation)

The present invention relates to organic and perovskite solar cell and optical detectors, in particular, relates to a multi-and fused ring conjugated macromolecule and its preparation method and application. The plurality of and fused ring conjugated macr