1,10-Phenanthroline, 3,8-dibromo-5,6-bis(octyloxy)-

Base Information

• Chemical Name: 1,10-Phenanthroline, 3,8-dibromo-5,6-bis(octyloxy)-
• CAS No.: 473255-19-5
• Molecular Formula: C₂₈H₃₈Br₂N₂O₂
• Molecular Weight: 594.43
• Mol file: 473255-19-5.mol

Synonyms:

Chemical Property of 1,10-Phenanthroline, 3,8-dibromo-5,6-bis(octyloxy)-

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: 1,10-Phenanthroline, 3,8-dibromo-5,6-bis(octyloxy)- is a derivative of π-conjugated poly(1,10-phenanthroline-3,8-diyl) (PPhen) featuring dibromo substitution at the 3,8-positions and octyloxy side chains at the 5,6-positions. 1,10-Phenanthroline, 3,8-dibromo-5,6-bis(octyloxy)- is synthesized via organometallic polycondensation using a Ni(0) complex, yielding soluble polymers with controlled molecular weights. The octyloxy groups enhance solubility and facilitate end-to-end packing in the solid state due to side-chain crystallization. The polymer exhibits strong dichroism in UV-vis absorption and photoluminescence, along with notable electron-accepting properties, enabling electrochemical reduction and stability in the reduced state. Additionally, it readily forms metal complexes, such as with [Ru(bpy)2]2?, and demonstrates n-doping behavior at low reduction potentials, highlighting its utility in optoelectronic and coordination chemistry applications.

Technology Process of 1,10-Phenanthroline, 3,8-dibromo-5,6-bis(octyloxy)-

There total 3 articles about 1,10-Phenanthroline, 3,8-dibromo-5,6-bis(octyloxy)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 28.0%

1-Iodooctane (629-27-6) + 3,8-dibromo-5,6-dihydroxy-1,10-phenanthroline (602331-26-0) → 3,8-dibromo-5,6-bis-octyloxy-[1,10]phenanthroline (473255-19-5)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; at 60 ℃; for 16h;

DOI:10.1021/ma0302659

Reference yield:

3,8-dibromo-1,10-phenathroline (100125-12-0) → 3,8-dibromo-5,6-bis-octyloxy-[1,10]phenanthroline (473255-19-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / HNO₃; H₂SO₄; KBr / 3 h / 130 °C

2.1: 100 percent / dithioxamide / ethanol / 12 h / 110 °C

3.1: NaH / dimethylsulfoxide / 12 h / 60 °C

3.2: 28 percent / dimethylsulfoxide / 16 h / 60 °C

With sulfuric acid; nitric acid; sodium hydride; dithiooxamide; potassium bromide; In ethanol; dimethyl sulfoxide;

DOI:10.1246/cl.2002.774

Reference yield:

3,8-dibromo-5,6-dihydro-1,10-phenanthroline-5,6-dione (602331-25-9) → 3,8-dibromo-5,6-bis-octyloxy-[1,10]phenanthroline (473255-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / dithioxamide / ethanol / 12 h / 110 °C

2.1: NaH / dimethylsulfoxide / 12 h / 60 °C

2.2: 28 percent / dimethylsulfoxide / 16 h / 60 °C

With sodium hydride; dithiooxamide; In ethanol; dimethyl sulfoxide;

DOI:10.1246/cl.2002.774

upstream raw materials:

1-Iodooctane

3,8-dibromo-5,6-dihydroxy-1,10-phenanthroline

3,8-dibromo-1,10-phenathroline

3,8-dibromo-5,6-dihydro-1,10-phenanthroline-5,6-dione