181144-56-9Relevant academic research and scientific papers
2D networks of rhombic-shaped fused dehydrobenzo[12]annulenes: Structural variations under concentration control
Tahara, Kazukuni,Okuhata, Satoshi,Adisoejoso, Jinne,Lei, Shengbin,Fujita, Takumi,De Feyter, Steven,Tobe, Yoshito
supporting information; experimental part, p. 17583 - 17590 (2010/04/01)
A series of alkyl- and alkoxy-substituted rhombic-shaped bisDBA derivatives 1a-d, 2a, and 2b were synthesized for the purpose of the formation of porous networks at the 1,2,4-trichlorobenzene (TCB)/graphite interface. Depending on the alkyl-chain length and the solute concentration, bisDBAs exhibit five network structures, three porous structures (porous A, B, and C), and two nonporous structures (nonporous D and E), which are attributed to their rhombic core shape and the position of the substituents. BisDBAs 1a and 1b with the shorter alkyl chains favorably form a porous structure, whereas bisDBAs 1c and 1d with the longer alkyl chains are prone to form nonporous structures. However, upon dilution, nonporous structures are typically transformed into porous ones, a trend that can be understood by the effect of surface coverage, molecular density, and intermolecular interactions on the system's enthalpy. Furthermore, porous structures are stabilized by the coadsorption of solvent molecules. The most intriguing porous structure, the Kagome pattern, was formed for all compounds at least to some extent, and the size of its triangular and hexagonal pores could be tuned by the alkyl-chain length. The present study proves that the concentration control is a powerful and general tool for the construction of porous networks at the liquid-solid interface.
Synthesis of Diacetylene Macrocycles Derived from 1,2-Diethynylbenzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer
Zhou, Qin,Carroll, Patrick J.,Swager, Timothy M.
, p. 1294 - 1301 (2007/10/02)
Diacetylene macrocycles 2-4 (n=1-3) (R=H, C4H9, C6H13, C10H21, C12H25, OC10H21) have been prepared from the oxidative coupling of 1,2-diethynylbenzene derivatives.These compounds can be produced in useful quantities and are of interest as precursors to novel conjugated organic polymers.The reported results indicate that when the R groups are large the dimeric macrocycle (n=1) can be prepared in as high as 74percent yield from the corresponding 1,2-diethynylbenzene in a one-step procedure.An alternate multistep procedure was found to produce the tetrameric macrocycle (n=3,R=C6H13) in 45percent yield.The highly strained dimeric macrocycle was characterized by an X-ray structure and was found to be very reactive.The dimers undergo a rapid very exothermic polymerization at 100-125 deg C, indicative of a chain reaction.Reaction of the dimeric macrocycles with iodine results in intramolecular cyclization and a new 20? electron tetraiodide fused ring system.Reaction of the tetraiodide with oxygen produces a related compound in which two of the iodides have been converted to ketones.
