Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 7, 2000
Previous Article Next Article

Author affiliations

Abstract

Palladium-catalyzed cross-coupling between 3,4-dialkoxyphenylboronic acids (1ad) and 2,3,6,7,10,11-hexabromotriphenylene (2) provided 2,3,6,7,10,11-hexakis[3,4-bis(alkoxy)phenyl]triphenylenes, C18H6[C6H3(OCnH2n + 1)2]6 where n = 6, 8, 10, and 12 (3ad). Cyclodehydrogenation of the aryl-substituted triphenylenes 3ad using ferric chloride oxidation followed by methanol reduction produced 6,6′,6″,7,7′,7″,10,10′,10″,11,11′,11″-dodecaalkoxy-2,3′:3,2″:2′,3″-tris(triphenylenylene)s, C54H18(OCnH2n + 1)12 where n = 6, 8, 10, and 12 (4ad). The mesomorphic properties of the compounds 3ad and 4ad were investigated by differential scanning calorimetry (DSC) measurements, polarizing microscopy, and wide angle X-ray diffraction (WAXD). The triphenylenes 3ad exhibited a columnar mesophase in the range of 111–126, 85–104, 74–103, and 47–101 °C, respectively. Upon oxidation of the moiety, the columnar mesophases shift to higher temperatures and exist in a much broader range of temperatures: for the tris(triphenylenylene)s 4ad, they have been observed in the range of 180–430, 150–370, 120–322, and 104–306 °C, respectively. Finally, the self-assembly at the interface between a solution of 4c and a graphite substrate has been studied by scanning tunneling microscopy. Molecularly resolved imaging revealed a highly ordered monolayer exhibiting a two-dimensional hexagonal lattice.

Back to tab navigation

Article information


Submitted
11 Feb 2000
Accepted
17 Apr 2000
First published
13 Jun 2000

J. Mater. Chem., 2000,10, 1519-1525
Article type
Paper

Extended triphenylenes: synthesis, mesomorphic properties and molecularly resolved scanning tunneling microscopy images of hexakis(dialkoxyphenyl)triphenylenes and dodeca(alkoxy)tris(triphenylenylene)s

T. Yatabe, M. A. Harbison, J. D. Brand, M. Wagner, K. Müllen, P. Samorí and J. P. Rabe, J. Mater. Chem., 2000, 10, 1519
DOI: 10.1039/B001162M

Search articles by author

Spotlight

Advertisements