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Issue 13, 2007
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Controlling the lateral aggregation of perfluoroalkylated hexa-peri-hexabenzocoronenes†

Olivier F. Aebischer,a   Annina Aebischer,b   Bertrand Donnio,c   Bassam Alameddine,d   Massoud Dadras,e   Hans-Ulrich Güdel,b   Daniel Guillonc  and  Titus A. Jenny*a  
Author affiliations

* Corresponding authors

a Department of Chemistry, University of Fribourg, chemin du Musée 9, 1700 Fribourg, Switzerland
E-mail: titus.jenny@unifr.ch
Fax: +41 26 300 9739
Tel: +41 26 300 8778

b Department of Chemistry and Biochemistry, University of Bern, Feiestrasse 3, 3000 Bern 9, Switzerland
E-mail: guedel@iac.unibe.ch
Fax: +41 31 631 4399
Tel: +41 31 631 4249

c Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Groupe des Matériaux Organiques (GMO), UMR 7504, CNRS/Université Louis Pasteur, 23, rue du Loess, BP 43, 670334 Strasbourg Cedex 2, France
E-mail: bdonnio@ipcms.u-strasbg.fr
Fax: +33 38 810 7246
Tel: +33 38 810 7157

d Department of Chemistry, University of Balamand, Tripoli, Lebanon
E-mail: balameddine@hotmail.com
Fax: +961 166 3885
Tel: +961 693 0250

e Service for Microscopy and Nanoscopy, IMT, University of Neuchâtel, 2007 Neuchâtel, Switzerland
E-mail: massoud.dadras@unine.ch
Fax: +41 32 720 5711
Tel: +41 32 720 5248

Abstract

The investigation of two hexa-peri-hexabenzocoronene (HBC) derivatives carrying linear or branched perfluoroalkylated side chains is reported. Polycondensed aromatic hydrocarbons (PAH) such as HBC derivatives are well known to self-organize to form highly ordered monomolecular stacks, which in turn show a concentration- and solvent-dependent lateral aggregation. However, possible applications of self-assembled HBC derivatives require linear, laterally non-aggregated columnar structures. According to powder X-ray diffraction (XRD) and differential scanning calorimetry (DSC), HBC derivatives with linear perfluoroalkylated side chains show liquid crystalline (LC) properties whereas those with branched perfluoroalkylated side chains have an amorphous structure. The stacking behaviour and the lateral aggregation are found to be greatly influenced by changes in the medium, as shown by fluorescence spectroscopy and cryo-scanning electron microscopy (cryo-SEM).

Graphical abstract: Controlling the lateral aggregation of perfluoroalkylated hexa-peri-hexabenzocoronenes

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Publication details

The article was received on 03 Nov 2006, accepted on 04 Jan 2007 and first published on 25 Jan 2007


Article type: Paper
DOI: 10.1039/B616057C
J. Mater. Chem., 2007,17, 1262-1267

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    Controlling the lateral aggregation of perfluoroalkylated hexa-peri-hexabenzocoronenes

    O. F. Aebischer, A. Aebischer, B. Donnio, B. Alameddine, M. Dadras, H. Güdel, D. Guillon and T. A. Jenny, J. Mater. Chem., 2007, 17, 1262
    DOI: 10.1039/B616057C

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