2,9-bis[3-(dimethyloxidoamino)propyl]-Anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetrone
[CAS# 1558023-86-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Isoquinoline compound
• Name: 2,9-bis[3-(dimethyloxidoamino)propyl]-Anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetrone
• Synonyms: PDINO; 3,3'-(1,3,8,10-tetraoxoanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-2,9(1H,3H,8H,10H)-diyl)bis(N,N-dimethylpropan-1-amine oxide)
• Molecular Formula: C₃₄H₃₂N₄O₆
• Molecular Weight: 592.64
• CAS Registry Number: 1558023-86-1
• SMILES: C[N+](C)(CCCN1C(=O)C2=C3C(=CC=C4C3=C(C=C2)C5=C6C4=CC=C7C6=C(C=C5)C(=O)N(C7=O)CCC[N+](C)(C)[O-])C1=O)[O-]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

2,9-Bis[3-(dimethyloxidoamino)propyl]-anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetrone is a derivative of the anthraquinone family, a class of compounds well-known for their structural diversity and extensive applications in dyes, pigments, and functional materials. This compound is distinguished by its functionalized diisoquinoline framework and the presence of dimethylamino oxide side chains, which enhance its chemical versatility and functional potential.

The compound was first synthesized in the context of designing advanced materials with enhanced photophysical and electronic properties. Its synthesis involves the functionalization of an anthraquinone backbone through controlled reactions, introducing the 3-(dimethyloxidoamino)propyl side chains. The development of such derivatives has been driven by the growing demand for novel organic semiconductors and electroactive materials.

Structurally, the molecule combines a rigid planar core with flexible side chains, making it an excellent candidate for applications in optoelectronic devices. The electron-rich dimethylamino oxide groups contribute to charge transport and stability, while the anthraquinone framework absorbs light in a broad spectrum. These properties make it particularly suitable for use in organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and field-effect transistors (OFETs).

In applications, the compound has shown promise as a material in organic electronics. Its strong absorption in the visible and near-infrared regions, coupled with high thermal and chemical stability, makes it ideal for use in thin-film devices. In OPVs, it acts as a donor or acceptor material, facilitating efficient charge separation and transport. Research indicates that its incorporation into active layers enhances device performance, achieving improved power conversion efficiencies.

Furthermore, the compound has potential as a fluorescent probe or dye due to its high quantum yield and stability. Its tunable electronic properties allow for modifications to meet specific needs in fluorescence imaging or sensing applications. In the field of biomedical research, it may be used for studying biological processes or as a component in drug delivery systems.

Despite its promising features, challenges remain in the large-scale synthesis and cost-effectiveness of 2,9-bis[3-(dimethyloxidoamino)propyl]-anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetrone. Current research focuses on optimizing synthetic routes to reduce complexity and enhance yield. Additionally, efforts to improve its environmental stability and biocompatibility are underway to expand its applicability.

In conclusion, 2,9-bis[3-(dimethyloxidoamino)propyl]-anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetrone exemplifies the potential of functionalized anthraquinone derivatives in advanced materials science. Its unique properties pave the way for innovations in organic electronics and beyond, promising contributions to sustainable and high-performance technologies.