2-[(7-{4-[N,N-Bis(4-methylphenyl)amino]phenyl}-2,1,3-benzothiadiazol-4-yl)methylene]propanedinitrile
[CAS# 1393343-58-2]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: 2-[(7-{4-[N,N-Bis(4-methylphenyl)amino]phenyl}-2,1,3-benzothiadiazol-4-yl)methylene]propanedinitrile
• Synonyms: DTDCPB; 2-[[4-[4-(4-methyl-N-(4-methylphenyl)anilino)phenyl]-2,1,3-benzothiadiazol-7-yl]methylidene]propanedinitrile
• Molecular Formula: C₃₀H₂₁N₅S
• Molecular Weight: 483.59
• CAS Registry Number: 1393343-58-2
• EC Number: 802-697-4
• SMILES: CC1=CC=C(C=C1)N(C2=CC=C(C=C2)C)C3=CC=C(C=C3)C4=CC=C(C5=NSN=C45)C=C(C#N)C#N

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 285-290 ºC (Expl.)
• Index of Refraction: 1.719, Calc.^*
• Boiling Point: 704.4±60.0 ºC (760 mmHg), Calc.^*
• Flash Point: 379.8±32.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302+H312+H332-H302-H312-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332

Discovory and Applicatios

2-[(7-{4-[N,N-Bis(4-methylphenyl)amino]phenyl}-2,1,3-benzothiadiazol-4-yl)methylene]propanedinitrile is an advanced organic compound that has garnered significant attention for its potential applications in the field of optoelectronics and organic light-emitting devices. The unique combination of its electron-donating and electron-accepting units makes it particularly useful for constructing high-performance materials with desirable electronic properties. This molecule is known for its extended conjugated system, which provides excellent charge transport and photoluminescent characteristics.

The discovery of this compound is rooted in the development of donor-acceptor (D-A) systems for organic electronics. In this compound, the donor unit is represented by the N,N-bis(4-methylphenyl)amino group, which is attached to a phenyl ring. The acceptor unit is the benzothiadiazole core, known for its strong electron-withdrawing properties. The presence of the propanedinitrile group further enhances the electron-accepting capability of the molecule. This D-A architecture facilitates intramolecular charge transfer, which is a critical feature for achieving high-efficiency light emission and charge transport.

The synthesis of 2-[(7-{4-[N,N-Bis(4-methylphenyl)amino]phenyl}-2,1,3-benzothiadiazol-4-yl)methylene]propanedinitrile typically involves a multi-step process. The initial step includes the preparation of the benzothiadiazole core through cyclization reactions involving diamines and sulfur-based reagents. The donor unit, N,N-bis(4-methylphenyl)amino, is introduced via palladium-catalyzed cross-coupling reactions, such as the Buchwald-Hartwig amination. Finally, the methylene-propanedinitrile moiety is appended through a Knoevenagel condensation reaction using malononitrile and an appropriate aldehyde derivative. Each step requires careful control of reaction conditions to achieve high yields and purity.

The primary application of this compound is in organic light-emitting diodes (OLEDs). The donor-acceptor structure of the molecule allows for efficient electron-hole recombination, resulting in high luminance and color purity. The N,N-bis(4-methylphenyl)amino group provides good hole-transporting properties, while the benzothiadiazole and propanedinitrile units enhance electron affinity, making the molecule suitable for use as an emissive layer in OLED devices. These properties contribute to the overall performance of OLEDs, including high quantum efficiency and stability.

Another promising application of this compound is in the development of organic photovoltaics (OPVs). The strong intramolecular charge transfer facilitated by the donor-acceptor system allows for efficient absorption of light and separation of charge carriers, which are essential for converting sunlight into electricity. Researchers have explored incorporating this molecule into bulk-heterojunction solar cells, where it acts as an electron donor material that interacts with fullerene or non-fullerene acceptors to achieve high power conversion efficiency.

In addition to OLEDs and OPVs, 2-[(7-{4-[N,N-Bis(4-methylphenyl)amino]phenyl}-2,1,3-benzothiadiazol-4-yl)methylene]propanedinitrile has potential uses in organic field-effect transistors (OFETs) due to its balanced charge transport properties. The extended conjugated system and molecular planarity allow for efficient π-π stacking, which facilitates charge mobility in thin-film devices. This makes it a suitable candidate for flexible electronics and next-generation display technologies.

Research continues to explore the optimization of this molecule for various applications, including modifying its structure to fine-tune its optical and electronic properties. The versatility of the donor-acceptor architecture ensures that this compound remains a valuable component in the field of organic semiconductors, contributing to advancements in energy-efficient technologies and flexible electronic devices.