N,N'-di(2-ethylhexyl)-1,7-di(thiophen-2-yl)perylene-3,4,9,10-tetracarboxylic acid bisimide

Base Information

• Chemical Name: N,N'-di(2-ethylhexyl)-1,7-di(thiophen-2-yl)perylene-3,4,9,10-tetracarboxylic acid bisimide
• CAS No.: 851786-19-1
• Molecular Formula: C₄₈H₄₆N₂O₄S₂
• Molecular Weight: 779.036
• Mol file: 851786-19-1.mol

Synonyms:

Chemical Property of N,N'-di(2-ethylhexyl)-1,7-di(thiophen-2-yl)perylene-3,4,9,10-tetracarboxylic acid bisimide

Chemical Property:

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N'-di(2-ethylhexyl)-1,7-di(thiophen-2-yl)perylene-3,4,9,10-tetracarboxylic acid bisimide

There total 4 articles about N,N'-di(2-ethylhexyl)-1,7-di(thiophen-2-yl)perylene-3,4,9,10-tetracarboxylic acid bisimide 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: 90.0%

N,N'-di(2-ethylhexyl)-1,7-dibromoperylene-3,4,9,10-bisdicarboximide (851786-15-7) + tributyl(thien-2-yl)stannane (54663-78-4) → N,N'-di(2-ethylhexyl)-1,7-dithien-2-yl-3,4,9,10-perylenediimide (851786-19-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 110 ℃; Inert atmosphere;

DOI:10.1039/b923452g

Reference yield: 83.0%

N,N'-di(2-ethylhexyl)-1,7-dibromoperylene-3,4,9,10-bisdicarboximide (851786-15-7) + thiophene boronic acid (6165-68-0) → N,N'-di(2-ethylhexyl)-1,7-dithien-2-yl-3,4,9,10-perylenediimide (851786-19-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; water; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol1023486

Reference yield:

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → N,N'-di(2-ethylhexyl)-1,7-dithien-2-yl-3,4,9,10-perylenediimide (851786-19-1)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid; bromine

2: 1-methyl-pyrrolidin-2-one

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; water / 24 h / 80 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; bromine; potassium carbonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water; 3: Suzuki coupling;

DOI:10.1021/ol1023486

upstream raw materials:

N,N'-di(2-ethylhexyl)-1,7-dibromoperylene-3,4,9,10-bisdicarboximide

tributyl(thien-2-yl)stannane

thiophene boronic acid

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

Refernces

• 1、 Zhou, Erjun,Tajima, Keisuke,Yang, Chunhe,Hashimoto, Kazuhito. "Band gap and molecular energy level control of perylene diimide-based donor-acceptor copolymers for all-polymer solar cells". experimental part. p. 2362 - 2368. Retrieved 2010/09/04.