PNDIT-F3N-Br
[CAS# 2169941-79-9]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: PNDIT-F3N-Br
• Synonyms: Poly[[2,7-bis(2-ethylhexyl)-1,2,3,6,7,8-hexahydro-1,3,6,8-tetraoxobenzo[lmn] [3,8]phenanthroline-4,9-diyl]-2,5-thiophenediyl[9,9-bis[3�((N,N-dimethyl)-N- ethylammonium)]propyl]-9H-fluorene-2,7-diyl]-2,5-thiophenediyl]
• Molecular Formula: (C₆₅H₈₀N₄O₄S₂)_n ^.₂Br
• Molecular Weight: ~40000
• CAS Registry Number: 2169941-79-9
• SMILES: C15=C(C=C3C2=C1C(=CC(=C2C(N(C3=O)CC(CC)CCCC)=O)C4=CC=C(S4)C)C(N(C5=O)CC(CC)CCCC)=O)C6=CC=C(S6)C7=C9C(=CC=C7)C8=C(C=C(C=C8)C)C9(CCC[N+](C)(C)CC)CCC[N+](C)(C)CC.[Br-].[Br-]

Properties

• Solubility: soluble (DMSO, DMF), insoluble (CHCl3)

Discovory and Applicatios

PNDIT-F3N-Br is a brominated naphthalene diimide (NDI)-based polymeric material designed for advanced applications in organic electronic devices. Its structure combines a naphthalene diimide backbone, known for excellent electron-transport characteristics, with fluorine substituents and a bromine atom that enable improved chemical reactivity and device performance. PNDIT-F3N-Br has gained attention in the field of organic photovoltaics (OPVs), organic field-effect transistors (OFETs), and other optoelectronic devices due to its tunable electronic properties and high stability.

The discovery of PNDIT-F3N-Br emerged from efforts to improve the performance of n-type semiconducting polymers. Incorporating fluorine atoms into the NDI core enhances electron affinity, contributing to a lower LUMO (lowest unoccupied molecular orbital) energy level. This feature is particularly advantageous in improving the material's electron mobility and air stability, critical factors for n-type materials in organic electronics. The bromine substituent adds functionalization versatility, facilitating further chemical modifications or polymer integration through coupling reactions.

PNDIT-F3N-Br is synthesized through polymerization techniques that leverage the reactivity of the bromine group for controlled molecular architecture. This precision enables the production of well-defined polymer chains with optimized molecular weights and polydispersity, essential for reproducible electronic performance. Its molecular design also supports self-assembly into well-ordered nanostructures, contributing to efficient charge transport.

In organic photovoltaic devices, PNDIT-F3N-Br acts as an acceptor material, partnering with donor polymers to create efficient bulk-heterojunction (BHJ) systems. Its strong electron-accepting ability and excellent phase separation characteristics with donor materials enhance light absorption, charge separation, and transport. These features contribute to higher power conversion efficiencies (PCEs) in OPV devices. For OFETs, the material demonstrates high electron mobility and operational stability, key parameters for next-generation thin-film transistors.

The versatility of PNDIT-F3N-Br extends to its use in all-polymer solar cells (all-PSCs), where it pairs with donor polymers to form devices without the need for small-molecule acceptors. This compatibility simplifies device fabrication processes and enhances environmental sustainability by eliminating certain solvents typically required for fullerene-based systems.

Despite its advantages, challenges associated with PNDIT-F3N-Br include scaling up its synthesis and addressing the environmental impact of its halogenated components. Current research focuses on optimizing synthetic methods to reduce production costs and exploring greener fabrication techniques. Moreover, ongoing studies aim to improve the polymer's compatibility with emerging device architectures and develop strategies for recycling electronic waste.

In summary, PNDIT-F3N-Br represents a significant advancement in the development of high-performance n-type polymers. Its tailored molecular structure enables exceptional performance in a range of organic electronic applications, solidifying its role in the advancement of renewable energy technologies and sustainable electronics.