Please use this identifier to cite or link to this item:
|Title:||Synthesis, self-assembly, and charge transporting property of contorted tetrabenzocoronenes||Authors:||Zhang, X.
|Issue Date:||3-Dec-2010||Citation:||Zhang, X., Jiang, X., Zhang, K., Mao, L., Luo, J., Chi, C., Chan, H.S.O., Wu, J. (2010-12-03). Synthesis, self-assembly, and charge transporting property of contorted tetrabenzocoronenes. Journal of Organic Chemistry 75 (23) : 8069-8077. ScholarBank@NUS Repository. https://doi.org/10.1021/jo101701k||Abstract:||A facile route has been developed for the preparation of a new family of contorted 1.2,3.4,7.8,9.10-tetrabenzocoronenes (TBCs). A two-step cyclization reaction, i.e., oxidative photocyclization followed by FeCl3-mediated intramolecular cyclodehydrogenation, was carried out on the olefin precursors to obtain the final TBC compounds. These new TBC molecules have contorted conformation due to steric overcrowding as disclosed by single-crystal crystallographic analysis. Nevertheless, they showed extended π-conjugation compared with coronene and exhibited strong aggregation in solution. The thermal behavior and self-assembly of TBC-C8 in solid were studied by a combination of thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), powder X-ray diffraction (XRD), scanning electron microscope (SEM), and transmission electron microscope (TEM). Compound TBC-C8 showed very good thermal and photostability and exhibited long-range ordered π-stacking in the bulk state. Moreover, uniform nanofibers with tens of micrometer length are formed in the drop-casted thin films. TBC-C8 also possesses a desirable HOMO energy level (-5.10 eV), which allows efficient charge injection from electrodes such as gold electrode. The charge carrier mobilities were determined by using the space-charge limited-current (SCLC) technique and high average hole mobility of 0.61 cm2 V-1 s-1 was obtained for TBC-C8. © 2010 American Chemical Society.||Source Title:||Journal of Organic Chemistry||URI:||http://scholarbank.nus.edu.sg/handle/10635/95165||ISSN:||00223263||DOI:||10.1021/jo101701k|
|Appears in Collections:||Staff Publications|
Show full item record
Files in This Item:
There are no files associated with this item.
checked on Jun 14, 2021
WEB OF SCIENCETM
checked on Jun 14, 2021
checked on Jun 8, 2021
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.