170698-86-9

Upstream product

• 15890-72-9 laurylmagnesium bromide 
• 126930-72-1 1-bromo-4-dodecylbenzene 
• 1066-54-2 trimethylsilylacetylene 
• 108-86-1 bromobenzene 
• 112-16-3 n-dodecanoyl chloride 
• 231606-35-2 1-(4-bromo-phenyl)-dodecan-1-one 
• 170698-87-0 4-dodecyl-1-(trimethylsilylethynyl)benzene 
• 170698-90-5 1-dodecyl-4-iodobenzene 
• 104-42-7 4-dodecylaniline 
• 135329-97-4 4,4'-Didodecyl-trans-stilbene 
• 18869-30-2 (E)-4,4'-dibromostilbene 
• 327603-59-8 1,2-Dibromo-1,2-bis(4-dodecylphenyl)ethane 
• 88020-03-5 4-n-dodecylphenylacetylene 

Downstream Products

• 217489-65-1 2,3,4,5-tetrakis(4-dodecyl-phenyl)-cyclopentadienone 
• 327603-95-2 2,5-bis(4-bromophenyl)-3,4-di(4-dodecylphenyl)cyclopenta-2,4-dien-1-one 
• 1431529-81-5 1,2-bis(4-chlorophenyl)-3,6-bis(biphenyl-3-yl)-4,5-bis(4-dodecylphenyl)benzene 
• 156733-60-7 1,2-bis-(4-dodecylphenyl)ethane-1,2-dione 

Relevant academic research and scientific papers

Discotic liquid crystals as novel corrosion-resistant coatings

A discotic liquid crystal (DLC), HBC-C12, coating was successfully applied to improve the corrosion resistance of an iron surface. The iron surface with the DLC-coating exhibited improved corrosion resistance in various environments, including exposure to

Contorted aromatics: Via a palladium-catalyzed cyclopentannulation strategy

We show that a new class of contorted polycyclic aromatic hydrocarbons (PAHs) containing five-membered rings can be prepared via a palladium-catalyzed cyclopentannulation followed by Scholl cyclodehydrogenation. The annulation chemistry can be accomplished between a di-arylethynylene and an appropriate aryl-dibromide to form 1,2,6,7-tetraarylcyclopenta[hi]aceanthrylenes and 1,2,6,7-tetraaryldicyclopenta[cd,jk]pyrenes. Scholl cyclodehydrogenation to close the externally fused aryl groups was accomplished only with properly arranged alkoxy substitutions and provides access to the pi-extended 2,7,13,18-tetraalkoxytetrabenzo[f,h,r,t]rubicenes and 2,7,13,18-tetraalkoxydibenzo[4,5:6,7]indeno[1,2,3-cd]dibenzo[4,5:6,7]indeno[1,2,3-jk]pyrenes. The final compounds each possess apparent [4]helicene-like arrangements with fused five-membered rings; however, only the 2,7,13,18-tetraalkoxytetrabenzo[f,h,r,t]rubicenes contort out of planarity owing to an additional [5]helicene like arrangement. Single crystal analysis of the contorted aromatic shows the PAHs stack in a lock-and-key like arrangement and pi-stack in a columnar arrangement. Solution-phase aggregation, as well as liquid crystalline mesophases, were found for derivatives with suitably attached solubilizing chains.

Synthesis and self-assembly of functionalized hexa-peri-hexabenzocoronenes

Monolayers of hexa-alkyl substituted derivatives of hexa-peri-hexabenzocoronene (HBC) 1b have previously been investigated by scanning tunneling microscopy (STM) and scanning tunneling spectroscopy (STS). It is expected that different functional groups (electron donating or withdrawing) connected to the aromatic core will influence the packing pattern and possibly the current-voltage characteristics as well. In order to provide suitable model systems, a new synthetic approach to synthesize functionalized HBC derivatives has been developed. This was accomplished by [4+2]-cycloaddition of suitably bromo-substituted diphenyl-acetylenes and 2,3,4,5-tetraarylcyclo-penta-2,4-dien-1-ones followed by an oxidative cyclodehydrogenation with iron(III) chloride/nitromethane. Using this strategy three different substitution patterns were synthesized: 2-bromo-5,8, 11,14,17-pentadodecylhexa-peri-hexabenzocoronene (2a), 2,5-dibromo-8,11,14,17-pentadodecylhexa-peri-hexabenzocoronene (2b), and 2,11-dibromo-5,8,14,17-pentadodecylhexa-peri-hexabenzocoronene (2c). These bromo-substituted HBC derivatives were subjected to palladium catalyzed coupling reactions to give donor (alkoxy, amino) as well as acceptor (ester, cyano) substituted derivatives. The self-assembly of these new HBC derivatives was studied in the bulk as well as at an interface. DSC, optical microscopy, and X-ray diffraction revealed the existence of columnar mesophases. The bulk structure in the mesophase is largely insensitive to changes of the substitution pattern; however, in situ scanning tunneling microscopy at the solid-fluid interface between an organic solution of the HBC derivative and highly oriented pyrolytic graphite reveals different packing patterns of the first adsorbed monolayer.

Diodenartige Strom-Spannungs-Kennlinie durch ein einzelnes Molekuel - Rasttertunnel - spektroskopie mit submolekularer Aufloesung an einem alkylierten, peri-kondensierten Hexabenzocoronen

Stichworte: Arene, Einzelmolekuelspektroskopie, Rastertunnel-mikroskopie