Heptahelicene

Base Information

• Chemical Name: Heptahelicene
• CAS No.: 16914-68-4
• Molecular Formula: C₃₀H₁₈
• Molecular Weight: 378.473
• DSSTox Substance ID: DTXSID50168664
• Nikkaji Number: J55.595I
• Wikidata: Q27115578
• Metabolomics Workbench ID: 54838
• Mol file: 16914-68-4.mol

Synonyms:heptahelicene;16914-68-4;[7]helicene;Dinaphtho[2,1-c:1',2'-g]phenanthrene;(7)Helicene;Dinaphtho(2,1-c:1',2'-g)phenanthrene;heptacyclo[16.12.0.02,15.03,12.04,9.021,30.024,29]triaconta-1(18),2(15),3(12),4,6,8,10,13,16,19,21(30),22,24,26,28-pentadecaene;CHEBI:33153;ZADYHNRFHQXTOH-UHFFFAOYSA-;DTXSID50168664;Dinaphtho[2,1-c:1/',2/'-g]phenanthrene;Q27115578

Chemical Property of Heptahelicene

Chemical Property:

• Vapor Pressure: 2E-17mmHg at 25°C
• Boiling Point: 677°C at 760 mmHg
• Flash Point: 360.6°C
• PSA: 0.00000
• Density: 1.286g/cm³
• LogP: 8.60580
• XLogP3: 9.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 378.140850574
• Heavy Atom Count: 30
• Complexity: 568

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=C2C4=C(C=CC5=C4C6=C(C=C5)C=CC7=CC=CC=C76)C=C3
• Uses: Heptahelicene when ordered in monolayers adsorbed on metal surfaces leads to a preferential transmission of one longitudinally polarized spin component.

Technology Process of Heptahelicene

There total 26 articles about Heptahelicene 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%

3,6-distyrylphenanthrene (694502-83-5) → heptahelicene (59177-52-5,20508-10-5,16914-68-4,40122-35-8)

Guidance literature:

With iodine; methyloxirane; In toluene; UV-irradiation;

DOI:10.1002/ejoc.200300470

Reference yield: 81.0%

3,3'-divinyl-4,4'-biphenanthryl → heptahelicene (59177-52-5,20508-10-5,16914-68-4,40122-35-8)

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; at 100 ℃; for 1h; microwave irradiation;

DOI:10.1002/anie.200504150

Reference yield: 75.0%

3,3'-bis-bromomethyl-[4,4']biphenanthrenyl (221683-80-3) → heptahelicene (59177-52-5,20508-10-5,16914-68-4,40122-35-8)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at 0 ℃; for 0.166667h;

DOI:10.1016/S0040-4039(98)02670-7

upstream raw materials:

1,2-Di-(3-phenanthryl)ethylen, cis

1,2-di(3-phenanthryl)ethylene

9-Bromo<7>helicene

distyryl-3,6-phenanthrene

Downstream raw materials:

<7>-helicene

heptahelicene

Refernces

• 1、 Fujino, Shota,Yamaji, Minoru,Okamoto, Hideki,Mutai, Toshiki,Yoshikawa, Isao,Houjou, Hirohiko,Tani, Fumito. "Systematic investigations on fused π-system compounds of seven benzene rings prepared by photocyclization of diphenanthrylethenes". . p. 925 - 934. Retrieved 2017.
• 2、 Gingras, Marc,Dubois, Fabien. "Synthesis of carbohelicenes and derivatives by 'carbenoid couplings'". . p. 1309 - 1312. Retrieved 1999.
• 3、 Flammang-Barbieux et al.. "". . p. 743. Retrieved 1967.
• 4、 Collins, Shawn K.,Grandbois, Alain,Vachon, Martin P.,Cote, Julie. "Preparation of helicenes through olefin metathesis". . p. 2923 - 2926. Retrieved 2007/10/03.