22734-61-8

Basic information

• Product Name: 1H-Benz[f]indene-1,3(2H)-dione
• Synonyms: Benz--indan-1,3-dion;indan-1,3-dione;indane-1,3-dione;
• CAS NO: 22734-61-8
• Molecular Formula: C13H8O2
• Molecular Weight: 196.205
• Mol File: 22734-61-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1H-Benz[f]indene-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benz[f]indene-1,3(2H)-dione(22734-61-8)
• EPA Substance Registry System: 1H-Benz[f]indene-1,3(2H)-dione(22734-61-8)

Safety Data

• Hazardous Substances Data: 22734-61-8(Hazardous Substances Data)

Usage

Classification

Heterocyclic compound.

Structure

Distinctive bicyclic structure.

Occurrence

Commonly found in various plants.

Synthesis

Can be synthesized from the oxidation of indigo or from the fusion of aniline and chloral.

Color

Yellowish.

Primary use

Used in the synthesis of indoles.

Indoles' applications

Widely utilized in pharmaceuticals and agrochemicals.

Biological activities

Potential anticancer, antimicrobial, and anti-inflammatory properties.

Research value

Valuable chemical in medical research.

Other uses

Precursor for the production of dyes, pigments, and other organic compounds.

Upstream product

• 716-39-2 2,3-Naphthalenedicarboxylic anhydride 
• 1694-31-1 tert-butyl acetoacetate 
• 50919-54-5 naphthalene-2,3-dicarboxylic acid diethyl ester 
• 141-78-6 ethyl acetate 
• 141-97-9 ethyl acetoacetate 
• 2169-87-1 naphthalene-2,3-dicarboxylic acid 
• 13728-34-2 dimethyl 2,3-naphthalenedicarboxylate 

Downstream Products

• 20927-01-9 benzo[f]ninhydrin 
• 109410-75-5 2,2-dibromobenzoindan-1,3-dione 
• 75155-47-4 benzindane-1,2,3-trione 2-oxime 
• 76788-93-7 C₁₅H₁₆N₈ 
• 49561-93-5 2-nitrobenz[f]indane-1,3-dione 
• 75155-48-5 1,3-dihydroxy-1,3-diphenylbenzindan-2-one 2-oxime 
• 75155-48-5 (1S,3S)-1,3-Dihydroxy-1,3-diphenyl-1,3-dihydro-cyclopenta[b]naphthalen-2-one oxime 
• 75155-48-5 (1R,3S)-1,3-Dihydroxy-1,3-diphenyl-1,3-dihydro-cyclopenta[b]naphthalen-2-one oxime 
• 1470131-80-6 C₁₈H₁₁NO₂ 
• 2109805-70-9 (3-oxo-2,3-dihydro-1H-cyclopenta[b]naphthalen-1-ylidene)propanedinitrile 

Relevant articles and documents

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.

Spiroconjugated Donor-σ-Acceptor Charge-Transfer Dyes: Effect of the ?-Subsystems on the Optoelectronic Properties

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.

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.