Papers by Author: Yu Jiang

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Authors: Yu Jiang, Xu Ying Liu, Rui Cheng, Wen Guang Wang, Jia Ling Pu
Abstract: In this paper, a novel protocol of akylation to tolan using CuI/HMPA as catalyst for synthesizing alkyl-substituted hexabenzocoronene (HBC) was described. The key step in the route was the construction of tolan bearing 2 long side chains, which was completed in the first step via coupling reaction between 4, 4’-Bis (bromomethyl) tolan (1) and Grignard Reagent in a mild condition. Afterward, Co2(CO)8 catalyzed cyclotrimerization gave hexaphenylbenzene derivative (HPB) which could be easily separated by column chromatography and recrystalization. The planarization of HPB was carried out with FeCl3 /MeNO2 to afford the desired HBC with long odd-carbon alkyl chains in good overall yields.
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Authors: Xu Ying Liu, Yu Jiang, Rui Cheng, Wen Guang Wang, Jia Ling Pu
Abstract: Two HBC derivatives (HBC-C13 and HBC-C15), both containing 6 odd-carbon alkyl chains surrounding the rigid plane core, were investigated as discotic liquid crystal. The difference between their thermal behaviors has been investigated by using differential scanning calorimetry (DSC). Their mesomorphic phase behavior was observed by polarizing optical microscopy (POM). A remarkable odd-even effect in the phase transition temperatures was observed for all HBC derivatives (HBC-C12, HBC-C13, HBC-C14, HBC-C15 and HBC-C16).
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Authors: Xu Ying Liu, Yu Jiang, Wen Guang Wang, Jia Ling Pu
Abstract: Hexa-peri-Hexabenzocoronene (HBC), as the smaller graphene fragment consisting of 13 fused benzene rings, possesses a strong tendency to stack together via π-electronic interaction. In this paper, the 1,2-(4-bromomethyl-1-yl) acetylene was alkylated by Grignard reagent to form corresponding 1,2-bis(p-pentadecanylphenyl)acetylene. Cobalt(0)-catalyzed cyclotrimerization was carried out to give hexaphenylbenzene analogue. This step was followed by intramolecular cyclodehydrogenation to yield the desired product HBC-C15. The identity and purity of the new compound was confirmed by UV-vis spectrometer and 1H NMR spectrum. Its thermal behavior and self-assembly were studied by differential scanning calorimetry and polarizing optical microscopy.
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Authors: Yu Jiang, Wen Guang Wang, Rui Cheng, Teng Zhou Yang, Jia Ling Pu
Abstract: A novel dibromo-substituted HBC derivative, whose side chains contains oxygen heteroatoms, has been successfully synthesized by Diels-Alder reaction of asymmetric synthesis. It possesses bromo-functional groups to provide possibility to further synthesize more complex HBC derivatives. The final compound’s structure has been confirmed by 1HNMR, 13CNMR and MALDI-TOF mass spectrometry.
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