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Self-Assembly of 9,10-Bis(phenylethynyl) anthracene (BPEA) Derivatives: Influence of pi-pi and Hydrogen Bonding Interactions on Aggregate Morphology and Self-Assembly Mechanism

Lübtow, M and Helmers, I and Stepanenko, V and Queiroz De Albuquerque, R and Marder, TB and Fernández, G (2017) Self-Assembly of 9,10-Bis(phenylethynyl) anthracene (BPEA) Derivatives: Influence of pi-pi and Hydrogen Bonding Interactions on Aggregate Morphology and Self-Assembly Mechanism. Chemistry - A European Journal, 23 (25). pp. 6198-6205. ISSN 0947-6539

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Abstract

9,10-Bis(phenylethynyl)anthracenes (BPEAs) are an important class of dyes with various applications including chemiluminescence emitters, materials for photon upconversion and for optoelectronic devices. Some of these applications require control over the packing modes of the active molecules within the active layer, which can be effected by bottom-up self-assembly. Studies aimed at controlling the molecular organization of BPEAs have primarily focused on bulk or liquid crystal materials, while in-depth investigations of BPEA-based assemblies in solution remain elusive. In this article, we report the self-assembly of two new BPEA derivatives with hydrophobic side chains, one of them featuring amide functional groups (2) and the other one lacking them (1). Comparison of the self-assembly behaviour in solution of both systems via spectroscopic (UV/Vis, fluorescence and NMR), microscopic (AFM) and theoretical (PM6) studies reveals the crucial role of the amide groups in controlling the self-assembly. While for both systems the formation of H-type face-to-face -stacks is proposed, the interplay of -stacking and H-bonding is responsible of driving the formation of 1D stacks and increasing the binding constant two-to-three orders of magnitude. Our findings show that H-bonding is a prerequisite to create ordered BPEA assemblies in solution.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: M. Lübtow, I. Helmers, V. Stepanenko, R. Q. Albuquerque, T. B. Marder, G. Fernández, Chem. Eur. J. 2017, 23, 6198., which has been published in final form at http://dx.doi.org/10.1002/chem.201605989. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Uncontrolled Keywords: 03 Chemical Sciences
Subjects: Q Science > QD Chemistry
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Wiley
Date Deposited: 07 Feb 2017 11:27
Last Modified: 22 Jun 2017 10:16
DOI or Identification number: 10.1002/chem.201605989
URI: http://researchonline.ljmu.ac.uk/id/eprint/5460

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