190-24-9Relevant articles and documents
Synthesis and crystal packing of large polycyclic aromatic hydrocarbons: Hexabenzo[bc,ef,hi,kl,no,qr]coronene and dibenzo[fg,ij]phenanthro[9,10,1,2,3- pqrst]pentaphene
Kuebel, Christian,Eckhardt, Karin,Enkelmann, Volker,Wegner, Gerhard,Muellen, Klaus
, p. 879 - 886 (2000)
A detailed study of the oxidative cyclodehydrogenation of two oligophenylene precursors resulting in large polycyclic aromatic hydrocarbons (PAHs) which contain up to 42 carbon atoms gave insight into the reaction course. This study confirmed that the reaction occurs exclusively in an intramolecular fashion without the formation of organic side products. X-Ray diffraction, selected area electron diffraction, and low-dose high-resolution electron microscopy were used to analyse the effect of heat treatment and sublimation on the morphology and crystal structure of large PAHs, hexabenzo[bc,ef,hi,kl,no,qr]coronene (HBC) and dibenzo[fg,ij]phenanthro[9,10,1,2,3-pqrst]pentaphene (DBPP). HBC crystallizes in the γ-motif, as has been determined from single crystals previously. The experiments showed that small crystals exhibit some characteristic distortions of the unit cell. DBPP also crystallizes also in the γ-motif, but due to the 'double-bay area' in the periphery of the molecule channels with a diameter of about 4 A are formed in the crystal.
A slippery slope: Mechanistic analysis of the intramolecular scholl reaction of hexaphenylbenzene
Rempala, Pawel,Kroulik, Jiri,King, Benjamin T.
, p. 15002 - 15003 (2004)
DFT calculations support an arenium cation-based mechanism for the Scholl reaction converting hexaphenylbenzene to hexa-peri-benzocoronene. The curve connecting fully benzenoid intermediates on the potential energy diagram is convex. This "slippery slope" provides an explanation for the ease of this cascade Scholl reaction. The calculated reaction coordinate predicts that intermediates will not accumulate; this prediction is verified by experiment. Copyright
Preparation method for constructing hexabenzocoronene by utilizing polycyclic aromatic hydrocarbon phenanthrene in coal tar
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Paragraph 7-14, (2020/04/29)
The invention discloses a preparation method for constructing hexabenzocoronene by utilizing polycyclic aromatic hydrocarbon phenanthrene in coal tar. According to the method, polycyclic aromatic hydrocarbon phenanthrene in coal tar is used as a raw material and is subjected to an oxidation addition reaction with chromium trioxide to generate phenanthrenequinone, phenanthrenequinone and dibenzyl ketone are subjected to a nucleophilic addition elimination reaction in a potassium hydroxide methanol solution to generate 9, 10-phenanthro 1, 12-diphenyl cyclopentadiene ketone, 9, 10-phenanthro 1, 12-diphenyl cyclopentadiene ketone and diphenyl acetylene are subjected to a Diels-Alder cycloaddition reaction in a diphenyl ether solution to obtain 1, 2, 3, 4-tetraphenyl triphenylene, and finally,1, 2, 3, 4-tetraphenyl triphenylene and anhydrous ferric chloride are subjected to an oxidative cyclization dehydrogenation reaction to generate hexabenzocoronene. According to the invention, hexabenzocoronene is prepared by taking polycyclic aromatic hydrocarbon substance-phenanthrene in coal tar as a raw material. By reasonably planning the synthesis route, the yield of each step is increased, and the yield of hexabenzocoronene is increased. The method can be popularized and applied to the process of synthesizing graphene from other polycyclic aromatic hydrocarbons in the coal tar, so that high-added-value utilization of coal tar resources is improved.
Well-Defined Thiolated Nanographene as Hole-Transporting Material for Efficient and Stable Perovskite Solar Cells
Cao, Jing,Liu, Yu-Min,Jing, Xiaojing,Yin, Jun,Li, Jing,Xu, Bin,Tan, Yuan-Zhi,Zheng, Nanfeng
supporting information, p. 10914 - 10917 (2015/09/15)
Perovskite solar cells (PSCs) have been demonstrated as one of the most promising candidates for solar energy harvesting. Here, for the first time, a functionalized nanographene (perthiolated trisulfur-annulated hexa-peri-hexabenzocoronene, TSHBC) is employed as the hole transporting material (HTM) in PSCs to achieve efficient charge extraction from perovskite, yielding the best efficiency of 12.8% in pristine form. The efficiency is readily improved up to 14.0% by doping with graphene sheets into TSHBC to enhance the charge transfer. By the HOMO-LUMO level engineering of TSHBC homologues, we demonstrate that the HOMO levels are critical for the performance of PSCs. Moreover, beneficial from the hydrophobic nature of TSHBC, the devices show the improved stability under AM 1.5 illumination in the humidity about 45% without encapsulation. These findings open the opportunities for efficient HTMs based on the functionalized nanographenes utilizing the strong interactions of their functional groups with perovskite.