Diacenaphtho[1,2-b:1',2'-d]thiophene

Base Information

• Chemical Name: Diacenaphtho[1,2-b:1',2'-d]thiophene
• CAS No.: 203-42-9
• Molecular Formula: C24H12S
• Molecular Weight: 332.425
• Hs Code.: 2934999090
• European Community (EC) Number: 205-904-0
• NSC Number: 4725
• UNII: XC8TR84BWK
• DSSTox Substance ID: DTXSID10174185
• Nikkaji Number: J193.676J,J3.206.029C
• Wikidata: Q83044248
• Mol file: 203-42-9.mol

Synonyms:203-42-9;Diacenaphtho[1,2-b:1',2'-d]thiophene;Diacenaphtho(1,2-b:1',2'-d)thiophene;1,8-DINAPHTHYLENETHIOPHENE;EINECS 205-904-0;NSC 4725;NSC-4725;14-thiaheptacyclo[14.7.1.14,8.02,15.03,13.020,24.012,25]pentacosa-1(23),2(15),3(13),4,6,8(25),9,11,16,18,20(24),21-dodecaene;2,3:4,5-Di(1,8-naphthylene)thiophene;NSC4725;Diacenaphtho[1 2-b:1 2-d]thiophene;diacenaphthyleno-thiophene;XC8TR84BWK;Diacenaphtho[1,2'-d]thiophene;SCHEMBL4761255;C24H12S;DTXSID10174185;2,2'-Thio-1,1'-biacenaphthylene;2,5-Di(1,8-naphthylene)thiophene;C24-H12-S;AKOS024322995;Diacenaphtho[1,2-b:1,2-d]thiophene;Diacenaphtho[1,2-b:1,2-d]thiophene #;Diacenaphtheno[7,8-b:7^1^,8^1^-d]thiophene

Chemical Property of Diacenaphtho[1,2-b:1',2'-d]thiophene

Chemical Property:

• Melting Point: 278-280 °C
• Boiling Point: 577.9 °C at 760 mmHg
• Flash Point: 231 °C
• PSA: 28.24000
• Density: 1.484 g/cm³
• LogP: 7.34930
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 332.06597156
• Heavy Atom Count: 25
• Complexity: 508

Purity/Quality:

99%, ^*data from raw suppliers

DIACENAPHTHO(1,2-B 1',2'-D)THIOPHENE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C4=C(C3=CC=C2)SC5=C4C6=CC=CC7=C6C5=CC=C7
• Use Description: 1,8-Dinaphthylenethiophene is a chemical compound with versatile applications across different fields. In the field of organic electronics and semiconductors, it is used as a crucial building block for organic semiconductors and materials used in the fabrication of organic light-emitting diodes (OLEDs), organic photovoltaic (OPV) devices, and organic field-effect transistors (OFETs). Its π-conjugated structure facilitates charge transport, making it valuable for creating high-performance electronic devices. Additionally, in the realm of materials science, this compound can be incorporated into polymers to enhance their electrical conductivity, making it useful in the development of conductive coatings and materials. Furthermore, in research and development, it can be employed as a tool for studying the electronic properties of organic materials and advancing the field of organic electronics. Its adaptability as a semiconductor building block and material modifier underscores its significance in advancing electronic technology, materials science, and scientific research in various fields.

Technology Process of Diacenaphtho[1,2-b:1',2'-d]thiophene

There total 11 articles about Diacenaphtho[1,2-b:1',2'-d]thiophene 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: 91.0%

diacenaphtho[1,2-c:1',2'-e]-1,2-dithiin (668988-07-6) → 1,2-acenaphthenothiophene (203-42-9)

Guidance literature:

In benzene; for 0.5h; Irradiation;

DOI:10.1016/j.jorganchem.2003.09.031

Reference yield: 50.0%

Pt(1,5-cyclooctadiene)(C24H12S2) (668988-08-7) → Pt(1,5-cyclooctadiene)S + 1,2-acenaphthenothiophene (203-42-9)

Guidance literature:

In benzene; under N2, in absence of light; Pt complex dissolved in benzene; heated to reflux for 3 h; filtered through column of florisil; solvent removed by rotary evapn.; sepd. by TLC (hexane-CH2Cl2);

DOI:10.1016/j.jorganchem.2003.09.031

Reference yield: 48.0%

2-diazoacenaphthen-1-one (2008-77-7) → 1,1'-Bi(acenaphthen-1-ylidene)-2,2'-dione (24141-18-2) + 1,2-acenaphthenothiophene (203-42-9) + acenaphtho<1,2-c><1,2,3>thiadiazole + 1(2H)-acenaphthylenone (2235-15-6)

Guidance literature:

With Lawessons reagent; N,N,N,N,N,N-hexamethylphosphoric triamide; In benzene; Heating;

upstream raw materials:

2-diazoacenaphthen-1-one

acenaphthylene

acenaphthene quinone

C₂₄H₁₄S₂

Downstream raw materials:

acenaphtho[1,2-j]fluoranthene

1,8-Naphthalic anhydride

decacyclene

4,5-diphenyl-acenaphtho[1,2-j]fluoranthene

Refernces

• 1、 Morrison, Brian J.,Musgrave, Oliver C.. "Thiones as reactive intermediates in condensations of diketones with aromatics mediated by tetraphosphorus decasulfide". . p. 2725 - 2744. Retrieved 2007/10/03.
• 2、 Zimmermann, Klaus,Haenel, Matthias W.. "Novel Syntheses of Decacyclene by Deoxygenating Cyclotrimerisation of Acenaphthenequinone with Zero-valent Titanium or Phosphorus Pentasulfide". . p. 609 - 611. Retrieved 2007/10/03.