214-63-1Relevant academic research and scientific papers
Revisiting zethrene: Synthesis, reactivity and semiconductor properties
Shan, Liang,Liang, Zhixiong,Xu, Xiaomin,Tang, Qin,Miao, Qian
, p. 3294 - 3297 (2013)
Zethrene, a unique polycyclic aromatic hydrocarbon with formally fixed C-C double bonds, is predicted to have interesting properties and potential applications as an optical and electronic material. Here we report a novel synthesis of zethrene with improved yield, which presumably involves dinaphtho[10]-annulene as an unstable intermediate. With this convenient access to zethrene, we used zethrene as a p-type semiconductor in thin film transistors for the first time. It is found that Diels-Alder addition to the bay region of zethrene leads to new derivatives of benzo[pqr]naphtho[8,1,2-bcd]perylene, which behave as n-type organic semiconductors.
Nickel-catalyzed, cascade cycloadditions of 1-ethynyl-8-halonaphthalenes with nitriles: Synthesis, structure, and physical properties of new pyrroloarenes
Wu, Tsun-Cheng,Tai, Chia-Cheng,Tiao, Hsin-Chieh,Kuo, Ming-Yu,Wu, Yao-Ting
experimental part, p. 1930 - 1935 (2011/03/22)
The reaction of 1-ethynyl-8-halonaphthalenes 1 with nitriles in the presence of the catalytic system [NiBr2(dppe)]/Zn (dppe=1,2-bis(diphenylphosphino)ethane) is found to produce unusual pyrroloarenes 2. The carbon-nitrogen triple bond in nitril
Synthesis, structure, and photophysical properties of dibenzo-[de, mn]naphthacenes
Wu, Tsun-Cheng,Chen, Chia-Hua,Hibi, Daijiro,Shimizu, Akihiro,Tobe, Yoshito,Wu, Yao-Ting
experimental part, p. 7059 - 7062 (2010/11/05)
Zethrenes were synthesized by Pd-catalyzed cyclodimerization of 1-ethynyl-8-iodonaphthalenes. The structure of these cycloadducts was confirmed by X-ray crystal analysis. The bond lengths and bond alternation in the crystal structures reveal that the central two six-membered rings of the title compounds lack aromaticity.
On the Purported Structure of Cyclodecadinaphthalene
Gleiter, Rolf,Schaaf, Hans Peter,Rodewald, Hans,Jahn, Reiner,Irngartinger, Hermann
, p. 480 - 487 (2007/10/02)
The reaction of the bis(sulfonium salt) 7 in a solution of Na2CO3 in H2O/EtOH yielded three main products 8-10.The spectroscopic data of 8 were identical to those which led Mitchell and Sondheimer to assign them to cyclodecadinaphthalene (3).Our investigations show, however, that the correct structural assignment leads to the structure of 7,7a-dihydrodibenzonaphthacene (8).
Synthesis of Potentially Basic Hydrocarbons by Sulphur Extrusion and/or Bis-Wittig Reactions. Two Syntheses of Benzindenophenalene and a New Synthesis of Dibenzonaphthacene (Zethrene)
Kemp, William,Storie, Iain T.,Tulloch, Charles D.
, p. 2812 - 2817 (2007/10/02)
Macrocyclic bis-sulphides have been prepared from 1,2-, 2,3-, and 1,8-bis(bromomethyl)naphthalenes.Methylation of the bis-sulphides, followed by the Stevens rearrangement, gave the corresponding carbocycles with extra-annular sulphide groups; removal of these sulphide groups by Hofmann elimination led to spontaneous trans-annular condensation.Using this general method, two hydrocarbons were synthesized: benzindenophenalene and dibenzonaphthacene (or zethrene).An alternative synthetic route led to the synthesis of benzindenophenalene, using the Wittig reaction between naphthalene-2,3-carbaldehyde and 1,8-bis(triphenylphosphoniomethyl)naphthalene dibromide.
