Issue 17, 2013
From the journal:

RSC Advances

Synthesis and self-assembly of triphenylene-containing conjugated macrocycles†

Tanmoy Dutta,a   Yanke Che,b   Haizhen Zhong,c   John H. Laity,d   Vladimir Dusevich,e   James B. Murowchick,f   Ling Zangb  and  Zhonghua Peng*a  

* Corresponding authors

a Department of Chemistry, University of Missouri-Kansas City, Kansas City, MO 64110, United States
E-mail: pengz@umkc.edu
Fax: +1-816-235-2290
Tel: +1-816-235-2288

b Department of Materials Science & Engineering, University of Utah, Salt Lake City, UT 84108, United States

c Department of Chemistry, University of Nebraska-Omaha, Omaha, NE, United States

d Department of Cell Biology and Biophysics, University of Missouri-Kansas City, Kansas City, MO 64110, United States

e Department of Oral Biology, University of Missouri-Kansas City, Kansas City, MO 64110, United States

f Department of Geosciences, University of Missouri-Kansas City, Kansas City, MO 64110, United States

Abstract

Two imine-based shape-persistent macrocycles containing triphenylene building blocks, along with their noncyclic model compounds, have been synthesized. Their stable conformations are predicted by quantum mechanical calculations and confirmed by 2D NOESY NMR measurements. Compared to the noncyclic model compounds, the macrocycles (3 and 6) show a higher propensity for solution self-assembly due to their stronger π–π stacking interactions, and form micro-objects which exhibit an enhanced conductivity after doping. While both macrocycles have identical molecular geometries and very similar structures, their solution self-assembly leads to micro-objects with very different shapes. The two macrocycles also show different pH-dependent optical properties.

Graphical abstract: Synthesis and self-assembly of triphenylene-containing conjugated macrocycles

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Article information

DOI
https://doi.org/10.1039/C3RA23421E
Article type
Paper
Submitted
20 Dec 2012
Accepted
11 Feb 2013
First published
14 Feb 2013

RSC Adv., 2013,3, 6008-6015

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Synthesis and self-assembly of triphenylene-containing conjugated macrocycles

T. Dutta, Y. Che, H. Zhong, J. H. Laity, V. Dusevich, J. B. Murowchick, L. Zang and Z. Peng, RSC Adv., 2013, 3, 6008 DOI: 10.1039/C3RA23421E

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