A study of the structural effects on the liquid-crystalline properties of ionic perylenebis(dicarboximide)s using UV-Vis spectroscopy, polarized light microscopy, and NMR spectroscopy

Langmuir : the ACS Journal of Surfaces and Colloids
Suk-Wah Tam-ChangIsaac K Iverson

Abstract

Ionic perylenebis(dicarboximide)s 1-5 were synthesized. The aggregation and liquid-crystalline properties of these compounds in aqueous solutions were investigated. In the concentration range of approximately 5 x 10-7-5 x 10-4 M, the structures of the ammonium side chains and counterions did not have a significant effect on the electronic transition properties and H-aggregate formation of these compounds. However, the liquid-crystalline phase properties varied with the structure of the side chains and the counterions. Ionic perylenebis(dicarboximide)s 1, 3, and 5 with chloride ions formed nematic (N) phases from the isotropic (I) phase, while 2 and 4 with p-methylbenzenesulfonate ions formed chromonic ribbons from the I phase. Studies by polarized light microscopy and 2H NMR spectroscopy indicated that the N phase of 5 (with gem dimethyl groups) formed at higher concentrations than those observed for 1 and 3 at the same temperature. Furthermore, the N phase of 5 was less ordered compared to those of 1 and 3 at a similar concentration and temperature, presumably due to the bulkiness of the side chains of 5 that hindered the stacking and pi-interactions of the aromatic rings.

References

Feb 22, 2003·Angewandte Chemie·Suk-Wah Tam-ChangSean M Casey
Mar 9, 2005·Langmuir : the ACS Journal of Surfaces and Colloids·Tod SchneiderOleg D Lavrentovich
Dec 31, 2005·Physical Review. E, Statistical, Nonlinear, and Soft Matter Physics·Viva R HorowitzPeter J Collings
Jan 25, 2006·Chemical Communications : Chem Comm·Suk-Wah Tam-ChangIsaac K Iverson
Jul 21, 2006·The Journal of Physical Chemistry. B·Andrei F KostkoSrinivasa R Raghavan

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Citations

May 9, 2009·Journal of the American Chemical Society·Lei WuYan-Yeung Luk
Jun 30, 2011·Nanoscale Research Letters·Carlos Rodriguez-AbreuSeiji Motojima
Feb 21, 2014·Physical Chemistry Chemical Physics : PCCP·Subhasish RoyArindam Banerjee
Aug 14, 2015·Chemical Reviews·Frank WürthnerDavid Schmidt
Dec 25, 2015·The Journal of Physical Chemistry. B·J R MaganaCarlos Rodriguez-Abreu
May 11, 2012·Angewandte Chemie·Daniel GörlFrank Würthner
Nov 21, 2014·Physical Chemistry Chemical Physics : PCCP·Gerald R Van HeckeScott Rayermann
Jan 28, 2015·Chemical Communications : Chem Comm·Annike Weissenstein, Frank Würthner
Aug 4, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Geraldine EchueCharl F J Faul
Jun 10, 2008·Chemical Communications : Chem Comm·Suk-Wah Tam-Chang, Liming Huang
Nov 13, 2009·Physical Review. E, Statistical, Nonlinear, and Soft Matter Physics·Leela JoshiSatyendra Kumar
Apr 16, 2009·The Journal of Physical Chemistry. B·Heung-Shik ParkOleg D Lavrentovich

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