2,7-Bis[2-(dimethylamino)ethyl]benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone

Name: 2,7-Bis[2-(dimethylamino)ethyl]benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone
Brand: ChemScene
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CAS No. 22291-04-9
Cat. No. CS-0098905
Purity≥95%
MDL No.MFCD27923061

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2,7-Bis[2-(dimethylamino)ethyl]benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone|CS-0098905

Structure of 22291-04-9

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General Information

CAS No. 22291-04-9
Cat. No. CS-0098905
Purity ≥95%
MDL No. MFCD27923061
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₂H₂₄N₄O₄
Molecular Weight 408.45
Synonym(s) Naphthalenediimide
SMILES O=C(N(CCN(C)C)C(C1=C2C3=C(C(N4CCN(C)C)=O)C=C1)=O)C2=CC=C3C4=O

Description

This tetrone-based ligand features two dimethylaminoethyl side chains at the 2,7-positions, enabling enhanced solubility and metal coordination versatility. The extended aromatic core supports strong π-stacking interactions, while the electron-rich substituents facilitate redox activity in transition metal complexes. Designed for applications in catalysis and molecular sensing, this scaffold offers robust stability under standard bench conditions.

Application

2,7-Bis[2-(dimethylamino)ethyl]benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone serves as a versatile polycyclic ligand scaffold with enhanced solubility and electron-donating capacity due to its dimethylaminoalkyl side chains. It facilitates metal coordination in catalytic systems and functions effectively in the synthesis of luminescent complexes and functional materials, offering stability under standard reaction conditions and ease of purification.

Synthesis

Route1
- In-stock
  
  81-30-1
- 108-00-9
- ~89%
- In-stock
  
  22291-04-9
References
- Bioorganic and Medicinal Chemistry, , vol. 9, # 8 p. 2015 - 2024

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

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Computational Chemistry Data

TPSA 84.62
LogP 0.1888
H_Acceptors 8
H_Donors 0
Rotatable_Bonds 6

Other Classifications

Material Science Electronic Materials Org. Field- Effect Transistor

Material Science Electronic Materials Organic Transistor (OFET) Materials n-Type Organic Semiconductors

Key Words

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2,7-Bis[2-(dimethylamino)ethyl]benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone

CAS No. 22291-04-9

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