327603-95-2Relevant academic research and scientific papers
Direct synthesis of polyaromatic chains of tribenzopentaphene copolymers through cyclodehydrogenation of their poly-tetraphenylbenzene precursors
Alameddine, Bassam,Sobhana Anju, Rajamohanan,Shetty, Suchetha,Baig, Noorullah,Al-Mousawi, Saleh,Al-Sagheer, Fakhreia
, p. 3565 - 3572 (2017)
Three polyaromatic-based polymers are reported to contain co-monomers of trapezoidal tribenzopentaphene (TBP) polycyclic aromatic hydrocarbons. The synthetic strategy consists of initially making highly soluble tetraphenylbenzene copolymers 4a–c, followed
Synthesis of Arylamine Tribenzopentaphenes and Investigation of their Hole Mobility
Alameddine, Bassam,Rice, Andrew H.,Luscombe, Christine,Jenny, Titus A.
, p. 453 - 456 (2015)
We report the versatile synthesis of two tribenzo[fj,ij,rst]pentaphene (TBP) derivatives bearing two diarylamine substituents attached at the opposite ends of the aromatic core. Field effect transistor (FET) devices of the bis-diarylamine-TBP compounds we
Synthesis and self-assembly of functionalized hexa-peri-hexabenzocoronenes
Ito, Shunji,Wehmeier, Mike,Diedrich Brand,Kuebel, Christian,Epsch, Rebekka,Rabe, Juergen P.,Muellen, Klaus
, p. 4327 - 4342 (2007/10/03)
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.
