Please use this identifier to cite or link to this item: https://doi.org/10.1021/jo101701k
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dc.titleSynthesis, self-assembly, and charge transporting property of contorted tetrabenzocoronenes
dc.contributor.authorZhang, X.
dc.contributor.authorJiang, X.
dc.contributor.authorZhang, K.
dc.contributor.authorMao, L.
dc.contributor.authorLuo, J.
dc.contributor.authorChi, C.
dc.contributor.authorChan, H.S.O.
dc.contributor.authorWu, J.
dc.date.accessioned2014-10-16T08:44:35Z
dc.date.available2014-10-16T08:44:35Z
dc.date.issued2010-12-03
dc.identifier.citationZhang, 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
dc.identifier.issn00223263
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/95165
dc.description.abstractA 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.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1021/jo101701k
dc.sourceScopus
dc.typeArticle
dc.contributor.departmentCHEMISTRY
dc.description.doi10.1021/jo101701k
dc.description.sourcetitleJournal of Organic Chemistry
dc.description.volume75
dc.description.issue23
dc.description.page8069-8077
dc.description.codenJOCEA
dc.identifier.isiut000284519900009
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