217489-65-1

Upstream product

• 327603-59-8 1,2-Dibromo-1,2-bis(4-dodecylphenyl)ethane 
• 170698-86-9 4,4'-didodecyl-1,1'-diphenylacetylene 
• 135329-97-4 4,4'-Didodecyl-trans-stilbene 
• 15890-72-9 laurylmagnesium bromide 
• 18869-30-2 (E)-4,4'-dibromostilbene 
• 92186-08-8 4-Bromomethyldodecylbenzene 
• 231606-35-2 1-(4-bromo-phenyl)-dodecan-1-one 
• 126930-72-1 1-bromo-4-dodecylbenzene 
• 123-01-3 1-dodecylbenzene 
• 112-16-3 n-dodecanoyl chloride 
• 108-86-1 bromobenzene 
• 156733-60-7 1,2-bis-(4-dodecylphenyl)ethane-1,2-dione 
• 189139-40-0 1,3-bis(4-dodecylphenyl)-propan-2-one 

Downstream Products

• 352532-70-8 7,8,9,10-Tetrakis(4-dodecylphenyl)fluoranthene 

Relevant academic research and scientific papers

Novel perylene chromophores obtained by a facile oxidative cyclodehydrogenation route

New perylene chromophores, phenyl-substituted diindeno[1,2,3-cd: 1′,2′,3′-lm]perylenes 5a,b and 4,4′,7,7′-tetraphenyldiacenaphtho[1,2- k:1′,2′,k′]diindeno[1,2,3-cd:1′,2′,3′- me]perylenes 22a,b, have been synthesized from substituted fluoranthene derivatives 3 a,b and 4 a,b by means of a surprisingly simple oxidative cyclodehydrogenation reaction. The resulting chromophores, when substituted with alkyl chains at the periphery, show good solubility in organic solvents, and a full characterization of the novel red, green, and blue dyes by field-desorption mass spectrometry, UV/Vis and 1H and 13C NMR spectroscopy becomes possible.

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.